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2019 Volume 39 Issue 5
2019, 39(5): 1197-1213
doi: 10.6023/cjoc201811035
Abstract:
Oxiranes are a class of oxygen-containing three-membered cyclic compounds. Due to their distinctive structure and unique properties, they can undergo a variety of cycloaddition reactions with compounds bearing diverse unsaturated bonds. The recent advances in the cycloaddition of oxiranes with this kind of compounds over the past decade, including[3+2], [3+3] and[4+3] are summarized. Moreover, the prospects of future development are also discussed.
Oxiranes are a class of oxygen-containing three-membered cyclic compounds. Due to their distinctive structure and unique properties, they can undergo a variety of cycloaddition reactions with compounds bearing diverse unsaturated bonds. The recent advances in the cycloaddition of oxiranes with this kind of compounds over the past decade, including[3+2], [3+3] and[4+3] are summarized. Moreover, the prospects of future development are also discussed.
2019, 39(5): 1214-1225
doi: 10.6023/cjoc201812010
Abstract:
Light-emitting electrochemical cells (LECs), which contain ionic compounds in the light-emitting layer, have attracted considerable interest for their solid-statelighting and next generation display applications. Compared with conventional organic light-emitting diodes (OLEDs), LECs contain simple device architecture (generally only one light- emitting layer), and can use air-stable metals (e.g. Al, Ag and Au) as the cathodes directly. In particular, LECs based on ionic transition metal complexes (iTMCs) have received more attention because of their several advantages over conventional polymer-based LECs. For iTMCs-based LECs, no inorganic salt or ion-conducting polymer is needed because iTMCs are intrinsically ionic. Higher efficiency is expected for iTMCs-based LECs because iTMCs emit efficient phosphorescence at room temperature as they can harvest both singlet and triplet excitons. Compared to other iTMCs, ionic iridium complexes have been widely utilized in optoelectronics, owing to their relevant luminescent properties, such as high emission quantum yields, stability and easy tunability of the emission color. The recent research progress of iridium complexes applied in LECs, including their synthesis, structural characterization and optoelectronic properties is summarized. This review mainly focuses on the development of ionic iridium complex-based LECs with different light-emitting colors and the improvement of device performances. In addition, the future directions of iridium complexes in LECs are also discussed.
Light-emitting electrochemical cells (LECs), which contain ionic compounds in the light-emitting layer, have attracted considerable interest for their solid-statelighting and next generation display applications. Compared with conventional organic light-emitting diodes (OLEDs), LECs contain simple device architecture (generally only one light- emitting layer), and can use air-stable metals (e.g. Al, Ag and Au) as the cathodes directly. In particular, LECs based on ionic transition metal complexes (iTMCs) have received more attention because of their several advantages over conventional polymer-based LECs. For iTMCs-based LECs, no inorganic salt or ion-conducting polymer is needed because iTMCs are intrinsically ionic. Higher efficiency is expected for iTMCs-based LECs because iTMCs emit efficient phosphorescence at room temperature as they can harvest both singlet and triplet excitons. Compared to other iTMCs, ionic iridium complexes have been widely utilized in optoelectronics, owing to their relevant luminescent properties, such as high emission quantum yields, stability and easy tunability of the emission color. The recent research progress of iridium complexes applied in LECs, including their synthesis, structural characterization and optoelectronic properties is summarized. This review mainly focuses on the development of ionic iridium complex-based LECs with different light-emitting colors and the improvement of device performances. In addition, the future directions of iridium complexes in LECs are also discussed.
2019, 39(5): 1226-1243
doi: 10.6023/cjoc201810018
Abstract:
Cyanide ion has strong toxicity for mammals, because it can affect many normal function of body, such as blood vessels, visual, as well as central nervous system, heart, endocrine and metabolic system. In addition, the cyanide salts are widely used in the production of human life, especially in electroplating and plastic manufacturing, mining, gold and silver leather industry, metallurgy, etc., which resulting in the pollution of environment. Therefore, the artificial cyanide selective receptor or fluorescent sensor has attracted widely attention in the field of anionic recognition. Due to the advantages of simple synthesis method, low cost, fast response, colorimetry and/or fluorescence change before and after reaction with cyanide, chemical sensors have been deeply studied by many researchers in the past decades. Based on the reaction of cyanide ions in different media, the research progress of cyanide sensors is summarized since 2010 from four aspects:(1) identification of cyanide in pure organic phase, (2) identification of cyanide ions in aqueous media, (3) identification of cyanide ions in pure water phase, and (4) identification of cyanide ions in solid phase. These sensors for cyanide in solution and solid material test and detect cyanide by naked eyes, which realizes the convenient, fast and real-time detection of cyanide in environmental and food samples.
Cyanide ion has strong toxicity for mammals, because it can affect many normal function of body, such as blood vessels, visual, as well as central nervous system, heart, endocrine and metabolic system. In addition, the cyanide salts are widely used in the production of human life, especially in electroplating and plastic manufacturing, mining, gold and silver leather industry, metallurgy, etc., which resulting in the pollution of environment. Therefore, the artificial cyanide selective receptor or fluorescent sensor has attracted widely attention in the field of anionic recognition. Due to the advantages of simple synthesis method, low cost, fast response, colorimetry and/or fluorescence change before and after reaction with cyanide, chemical sensors have been deeply studied by many researchers in the past decades. Based on the reaction of cyanide ions in different media, the research progress of cyanide sensors is summarized since 2010 from four aspects:(1) identification of cyanide in pure organic phase, (2) identification of cyanide ions in aqueous media, (3) identification of cyanide ions in pure water phase, and (4) identification of cyanide ions in solid phase. These sensors for cyanide in solution and solid material test and detect cyanide by naked eyes, which realizes the convenient, fast and real-time detection of cyanide in environmental and food samples.
2019, 39(5): 1244-1262
doi: 10.6023/cjoc201811029
Abstract:
Isofurazan is composed of 1, 3, 4-oxadiazole and 1, 2, 4-oxadiazole, and the isofurazan compounds have gained considerable prominence as energetic compounds. This review focues on the two major classes of isofurazan energetic compounds and their energetic derivatives. The cyclization methods and reaction mechanism of isofurazans are presented. Several energetic compounds of isofurazans with excellent performances are highlighted, and their main physicochemical properties and detonation performances and their development prospect are discussed.
Isofurazan is composed of 1, 3, 4-oxadiazole and 1, 2, 4-oxadiazole, and the isofurazan compounds have gained considerable prominence as energetic compounds. This review focues on the two major classes of isofurazan energetic compounds and their energetic derivatives. The cyclization methods and reaction mechanism of isofurazans are presented. Several energetic compounds of isofurazans with excellent performances are highlighted, and their main physicochemical properties and detonation performances and their development prospect are discussed.
2019, 39(5): 1263-1276
doi: 10.6023/cjoc201811038
Abstract:
The phosphaalkenes, as an important part of organophosphorus chemistry, play a very important role in the field of homogeneous catalysis and functional materials due to special properties of P=C unit. However, the difficult access to phosphaalkene compounds and their less stability have severely retarded the progress of the phosphaalkene chemistry. In this paper, the recent advances in phosphaalkenes, introducing the properties, synthetic methods, and applications of phosphaalkenes to provide some reference for related researcher are reviewed.
The phosphaalkenes, as an important part of organophosphorus chemistry, play a very important role in the field of homogeneous catalysis and functional materials due to special properties of P=C unit. However, the difficult access to phosphaalkene compounds and their less stability have severely retarded the progress of the phosphaalkene chemistry. In this paper, the recent advances in phosphaalkenes, introducing the properties, synthetic methods, and applications of phosphaalkenes to provide some reference for related researcher are reviewed.
2019, 39(5): 1277-1283
doi: 10.6023/cjoc201811023
Abstract:
Furan, an important class of oxygen-containing five-membered heterocyclic compounds, is not only the fundamental structure of many natural products, drugs and biologically active molecules, but also an valuable intermediate in organic synthesis. Synthesis of polysubstituted furans has been one of the focus of organic chemists. In this paper, recent progress in the synthesis of polysubstituted furans since 2013, including disubstituted, trisubstituted, tetrasubstituted furans and benzofurans is reviewed.
Furan, an important class of oxygen-containing five-membered heterocyclic compounds, is not only the fundamental structure of many natural products, drugs and biologically active molecules, but also an valuable intermediate in organic synthesis. Synthesis of polysubstituted furans has been one of the focus of organic chemists. In this paper, recent progress in the synthesis of polysubstituted furans since 2013, including disubstituted, trisubstituted, tetrasubstituted furans and benzofurans is reviewed.
2019, 39(5): 1284-1292
doi: 10.6023/cjoc201809012
Abstract:
Cyclodextrin is a kind of cyclic oligosaccharide which is composed of the D-pyran glucose units connected with the α-1, 4-glycosidic bond. Cyclodextrin has the rigidly tapered cavity of hydrophobic inner and hydrophilic outer. Cyclodextrin has been attracted more and more attention from scientists since it was discovered, owning to its special space cavity of hydrophilic inner and hydrophilic outer. As an important industrial catalyst, transition metal catalyst can combine with the cyclodextrin system to simultaneously exert the catalytic properties of the metal and the molecular recognition and phase transfer of cyclodextrin, which greatly improves its catalytic performance. In this paper, the transition metal catalyzed organic reactions involving cyclodextrin are reviewed, and these reactions are described in terms of the metal valence from 0 to 4. Finally, the development and foreground of these co-catalyst systems involving metal and cyclodextrin are prospected. It is expected that the catalytic system will have a wider application in the future, and a more efficient and selective catalytic system will be continuously developed.
Cyclodextrin is a kind of cyclic oligosaccharide which is composed of the D-pyran glucose units connected with the α-1, 4-glycosidic bond. Cyclodextrin has the rigidly tapered cavity of hydrophobic inner and hydrophilic outer. Cyclodextrin has been attracted more and more attention from scientists since it was discovered, owning to its special space cavity of hydrophilic inner and hydrophilic outer. As an important industrial catalyst, transition metal catalyst can combine with the cyclodextrin system to simultaneously exert the catalytic properties of the metal and the molecular recognition and phase transfer of cyclodextrin, which greatly improves its catalytic performance. In this paper, the transition metal catalyzed organic reactions involving cyclodextrin are reviewed, and these reactions are described in terms of the metal valence from 0 to 4. Finally, the development and foreground of these co-catalyst systems involving metal and cyclodextrin are prospected. It is expected that the catalytic system will have a wider application in the future, and a more efficient and selective catalytic system will be continuously developed.
2019, 39(5): 1293-1303
doi: 10.6023/cjoc201810036
Abstract:
Organotitanium proves to be one of ideal organometallic candidates because of its low price, non-toxicity, diversified types, excellent chemo-, regio- and stereo-selectivities. The reactivity of organotitanium reagent could be easily controlled by ligands of central titanium atom. Recently, the coupling reactions of organotitanium reagent have attracted extensive attention. This review summerized recent progress in transiton metal-catalyzed coupling reactons of organotitanium reagents concerning their types.
Organotitanium proves to be one of ideal organometallic candidates because of its low price, non-toxicity, diversified types, excellent chemo-, regio- and stereo-selectivities. The reactivity of organotitanium reagent could be easily controlled by ligands of central titanium atom. Recently, the coupling reactions of organotitanium reagent have attracted extensive attention. This review summerized recent progress in transiton metal-catalyzed coupling reactons of organotitanium reagents concerning their types.
2019, 39(5): 1304-1315
doi: 10.6023/cjoc201809034
Abstract:
Imidazo[1, 2-a]pyridine compounds were 5- and 6-membered nitrogen heterocyclic compounds, which were found in various natural products and exhibited a wide range of pharmacological activities, and were widely used in medical chemistry. Imidazo[1, 2-a]pyridines have important research significance and broad medical application prospects, so the synthetic strategy literatures on the diversity of such compounds have been continuously reported. In recent years, green chemistry was one of the hot trends in contemporary chemistry. More and more attention is paid to green synthesis and constantly developing various green synthesis solutions. Among them, one-pot "multi-component" reaction, microwave reaction and solid phase synthesis, which were green and high-efficiency synthetic methods, have been the focus of research. From the three types of green synthesis methods, The research progress of imidazole[1, 2-a]pyridine green synthesis in recent years is summarized.
Imidazo[1, 2-a]pyridine compounds were 5- and 6-membered nitrogen heterocyclic compounds, which were found in various natural products and exhibited a wide range of pharmacological activities, and were widely used in medical chemistry. Imidazo[1, 2-a]pyridines have important research significance and broad medical application prospects, so the synthetic strategy literatures on the diversity of such compounds have been continuously reported. In recent years, green chemistry was one of the hot trends in contemporary chemistry. More and more attention is paid to green synthesis and constantly developing various green synthesis solutions. Among them, one-pot "multi-component" reaction, microwave reaction and solid phase synthesis, which were green and high-efficiency synthetic methods, have been the focus of research. From the three types of green synthesis methods, The research progress of imidazole[1, 2-a]pyridine green synthesis in recent years is summarized.
2019, 39(5): 1316-1322
doi: 10.6023/cjoc201903009
Abstract:
A copper(Ⅱ)-catalyzed aerobic oxidative coupling of aromatic sulfonyl hydrazides with amines for the synthesis of aromatic sulfonamides was described. In contrast to previously described methods, this reaction employs copper/O2 as the catalytic system, and generates N2 as the only byproduct, which provides an environmentally benign synthetic route for aromatic sulfonamides.
A copper(Ⅱ)-catalyzed aerobic oxidative coupling of aromatic sulfonyl hydrazides with amines for the synthesis of aromatic sulfonamides was described. In contrast to previously described methods, this reaction employs copper/O2 as the catalytic system, and generates N2 as the only byproduct, which provides an environmentally benign synthetic route for aromatic sulfonamides.
2019, 39(5): 1344-1353
doi: 10.6023/cjoc201811041
Abstract:
A series of novel 3-acetyl-4-hydrazinyl-5, 5-disubstitutedtetronic acid and (E/Z)-3-(1-hydrazinylethyli-dene)-5, 5-disubstitutedfuran-2, 4-dione derivatives were designed and synthesized, and four methyl 5-methyl pyrazole-4-carboxylate were obtained unexpectedly. Their structures were confirmed by high-resolution mass spectrum (HR-ESI-MS), 1H NMR, 13C NMR spectral data and X-ray diffraction. The bioassay results of the hydrazinyl compounds along with the amino analogues indicated that some compounds exhibited moderate to excellent fungicidal activities against phytopathagens. For example, compounds 5G, 5H, 5I and 5i showed 100% in vivo control efficacy against Colletotrichum lagenarium, and compound 5G also exhibited 100% in vivo control efficacy against Erysiphe graminis, Puccinia polysora and Colletotrichum lagenarium at 400 μg/mL. Compounds 5b, 5E and 6F showed 100% mortality against Plutella xylostella, compounds 6A, 6g and 6H exhibited 100% mortality against Myzus persicae, and compound 6b showed 100% mortality against Tetranychus cinnabarinus at 600 μg/mL. The 5, 5-spiro cyclohexyl moiety significantly improved the fungicidal activity of the tetronic acid derivatives, and the introduction of the substituted hydrazino group to the furan-2, 4-dione skeleton led to higher insecticidal and acaricidal activities. 5G and 5i were found to have the most potential to be further modified for searching new fungicide as the lead compounds.
A series of novel 3-acetyl-4-hydrazinyl-5, 5-disubstitutedtetronic acid and (E/Z)-3-(1-hydrazinylethyli-dene)-5, 5-disubstitutedfuran-2, 4-dione derivatives were designed and synthesized, and four methyl 5-methyl pyrazole-4-carboxylate were obtained unexpectedly. Their structures were confirmed by high-resolution mass spectrum (HR-ESI-MS), 1H NMR, 13C NMR spectral data and X-ray diffraction. The bioassay results of the hydrazinyl compounds along with the amino analogues indicated that some compounds exhibited moderate to excellent fungicidal activities against phytopathagens. For example, compounds 5G, 5H, 5I and 5i showed 100% in vivo control efficacy against Colletotrichum lagenarium, and compound 5G also exhibited 100% in vivo control efficacy against Erysiphe graminis, Puccinia polysora and Colletotrichum lagenarium at 400 μg/mL. Compounds 5b, 5E and 6F showed 100% mortality against Plutella xylostella, compounds 6A, 6g and 6H exhibited 100% mortality against Myzus persicae, and compound 6b showed 100% mortality against Tetranychus cinnabarinus at 600 μg/mL. The 5, 5-spiro cyclohexyl moiety significantly improved the fungicidal activity of the tetronic acid derivatives, and the introduction of the substituted hydrazino group to the furan-2, 4-dione skeleton led to higher insecticidal and acaricidal activities. 5G and 5i were found to have the most potential to be further modified for searching new fungicide as the lead compounds.
2019, 39(5): 1354-1361
doi: 10.6023/cjoc201810015
Abstract:
The 1, 3-dipolar cycloaddition of nitrilimines with methyl coumalate or pyranone worked efficiently in the presence of iPr2NEt under room temperature to give functionalized dihydropyrano[3, 2-c]pyrazol-5(1H)-one derivatives in high to excellent yields with excellent diastereoselectivities.
The 1, 3-dipolar cycloaddition of nitrilimines with methyl coumalate or pyranone worked efficiently in the presence of iPr2NEt under room temperature to give functionalized dihydropyrano[3, 2-c]pyrazol-5(1H)-one derivatives in high to excellent yields with excellent diastereoselectivities.
2019, 39(5): 1362-1371
doi: 10.6023/cjoc201812001
Abstract:
A series of bis(3, 4, 5-substituted pyrazolyl)methane derivatives were designed as candidates of high energy density materials (HEDMs). The heats of formation (HOFs), electronic structure, energetic properties and thermal stabilities were studied using density functional theory (DFT) method. The difluoroamino groups could increase energy gaps of electronic structure, density and detonation properties among the title compounds. Bis[3, 5-bis(difluoroamino)-4-nitropyrazolyl]methane (C2) had excellent properties of potential HEDM. Its crystal density (ρ, 2.11 g/cm3) and impact sensitivity (h50, 6.8 J) were even higher than those of hexanitrohexaazaisowurtzitane (CL-20), meanwhile its detonation velocity (D, 9.80 km/s) and detonation pressure (P, 46.62 GPa) were very close to CL-20.
A series of bis(3, 4, 5-substituted pyrazolyl)methane derivatives were designed as candidates of high energy density materials (HEDMs). The heats of formation (HOFs), electronic structure, energetic properties and thermal stabilities were studied using density functional theory (DFT) method. The difluoroamino groups could increase energy gaps of electronic structure, density and detonation properties among the title compounds. Bis[3, 5-bis(difluoroamino)-4-nitropyrazolyl]methane (C2) had excellent properties of potential HEDM. Its crystal density (ρ, 2.11 g/cm3) and impact sensitivity (h50, 6.8 J) were even higher than those of hexanitrohexaazaisowurtzitane (CL-20), meanwhile its detonation velocity (D, 9.80 km/s) and detonation pressure (P, 46.62 GPa) were very close to CL-20.
2019, 39(5): 1424-1428
doi: 10.6023/cjoc201812007
Abstract:
An electrochemical synthesis of tetrasubstituted hydrazines through dehydrogenative dimerization of secondary amines has been developed. The reactions are conducted in a simple undivided cell with constant current. The use of electricity to promote the reactions obviates the need for transition metal catalysts and oxidizing reagents, providing an efficient and sustainable access to tetrasubstituted hydrazines with diverse electronic properties.
An electrochemical synthesis of tetrasubstituted hydrazines through dehydrogenative dimerization of secondary amines has been developed. The reactions are conducted in a simple undivided cell with constant current. The use of electricity to promote the reactions obviates the need for transition metal catalysts and oxidizing reagents, providing an efficient and sustainable access to tetrasubstituted hydrazines with diverse electronic properties.
2019, 39(5): 1429-1435
doi: 10.6023/cjoc201810011
Abstract:
An efficient protocol for conversion of aldehyde and indole into bis(indolyl)methanes derivatives catalyzed by strong-acid cation exchange resin has been developed. The H2O was used as solution and recycle catalyst can be used six times. Various bis(indolyl)methanes derivatives were obtained in excellent yields.
An efficient protocol for conversion of aldehyde and indole into bis(indolyl)methanes derivatives catalyzed by strong-acid cation exchange resin has been developed. The H2O was used as solution and recycle catalyst can be used six times. Various bis(indolyl)methanes derivatives were obtained in excellent yields.
2019, 39(5): 1444-1449
doi: 10.6023/cjoc201901003
Abstract:
6-Methoxyquinazolinone-pyridine difluoroboron dyes (BODIQPys) have been synthesized in two simple steps with 2-amino-5-methoxybenzamide and 2-methylpyridines as starting materials. These quinazolinone-based difluoroboron (BF2) complexes exhibited highly efficient green luminescence and remarkable fluorescence in the solid-state with very large Stokes shift (Δλ up to 220 nm in MeCN). The introduction of methoxy group at 6-position of BODIQPy caused the red-shifted emission by the enhancement of charge transfer property. The introduction of halogen atom at pyridine moiety of BODIQPy can tune the LUMO levels in regularity while their HOMO levels remain intact.
6-Methoxyquinazolinone-pyridine difluoroboron dyes (BODIQPys) have been synthesized in two simple steps with 2-amino-5-methoxybenzamide and 2-methylpyridines as starting materials. These quinazolinone-based difluoroboron (BF2) complexes exhibited highly efficient green luminescence and remarkable fluorescence in the solid-state with very large Stokes shift (Δλ up to 220 nm in MeCN). The introduction of methoxy group at 6-position of BODIQPy caused the red-shifted emission by the enhancement of charge transfer property. The introduction of halogen atom at pyridine moiety of BODIQPy can tune the LUMO levels in regularity while their HOMO levels remain intact.
2019, 39(5): 1323-1332
doi: 10.6023/cjoc201811021
Abstract:
Oxime compounds were efficiently synthesized with aromatic or aliphatic ketones and hydroxylamine hydrochloride as raw materials in the PEG-400 solution, using cheap and readily available superfine kaolin as catalyst under microwave irradiation condition. The effects of the catalyst, the solvent type, reaction time, reaction temperature on the reaction were investigated. The structures of the products were detected by melting point, nuclear magnetic resonance, infrared spectroscopy and mass spectrometry data. This method has the advantages of short reaction times (5~15 min), good yields, and simple operation as well as environmental friendliness. In addition, the preliminary experiment shows that superfine kaolin could also catalyze transoximation reaction and preparation of oxime ether compounds under microwave irradiation with the yields of 42%~67% and 59%~72%.
Oxime compounds were efficiently synthesized with aromatic or aliphatic ketones and hydroxylamine hydrochloride as raw materials in the PEG-400 solution, using cheap and readily available superfine kaolin as catalyst under microwave irradiation condition. The effects of the catalyst, the solvent type, reaction time, reaction temperature on the reaction were investigated. The structures of the products were detected by melting point, nuclear magnetic resonance, infrared spectroscopy and mass spectrometry data. This method has the advantages of short reaction times (5~15 min), good yields, and simple operation as well as environmental friendliness. In addition, the preliminary experiment shows that superfine kaolin could also catalyze transoximation reaction and preparation of oxime ether compounds under microwave irradiation with the yields of 42%~67% and 59%~72%.
2019, 39(5): 1333-1343
doi: 10.6023/cjoc201812022
Abstract:
The PPh3 catalyzed Lu's[3+2] annulation of aurones with alkenoates has been developed to form spiro-[1-ben-zofuran-3-one-2, 5'-cyclopentene] polycyclic moiety. The usefulness of this strategy has been demonstrated by the use of a wide variety of substrates to give desired polycyclic compounds in high yield under mild and simple reaction condition. This methodology research offered a fine entry for synthesis of natural product applanatumin A and its analogues.
The PPh3 catalyzed Lu's[3+2] annulation of aurones with alkenoates has been developed to form spiro-[1-ben-zofuran-3-one-2, 5'-cyclopentene] polycyclic moiety. The usefulness of this strategy has been demonstrated by the use of a wide variety of substrates to give desired polycyclic compounds in high yield under mild and simple reaction condition. This methodology research offered a fine entry for synthesis of natural product applanatumin A and its analogues.
2019, 39(5): 1372-1382
doi: 10.6023/cjoc201812032
Abstract:
A series of nopinone-based thiazolyhydrazone derivatives were synthesized by using nopinone derivated from natural β-pinene as the starting material in three steps, including aldol reaction with aromatic aldehydes, condensation with aminothiourea, and cyclization with bromoacetophenone. The structures of synthesized compounds were characterized by 1H NMR, 13C NMR and HRMS. α-Amylase inhibitory activities of these compounds were also investigated. The results showed that 6 compounds among them had good inhibitory activities compared with the positive control acarbose. Especially, 4-(2-(2-(6, 6-dimethyl-3-(4-methylbenzylidene))bicyclo[3.1.1]heptane-2-ylidene)indolyl-4-thiazol-4-yl)phenol (SZ14) exhibited remarkable α-amylase inhibitory activity with IC50 value of 4.11 μmol/L. From the structure-activity relationship, the structure of R2 gave great influence on the activities of thiazolyhydrazone derivatives. The kinetic inhibition study revealed that those 6 compounds were the noncompetitive inhibitor against α-amylase. It was used for molecular docking study to find out binding affinities for thiazolylhydrazone derivatives, and the binding mode of compound SZ14 with α-amylase was primarily investigated with molecular docking method.
A series of nopinone-based thiazolyhydrazone derivatives were synthesized by using nopinone derivated from natural β-pinene as the starting material in three steps, including aldol reaction with aromatic aldehydes, condensation with aminothiourea, and cyclization with bromoacetophenone. The structures of synthesized compounds were characterized by 1H NMR, 13C NMR and HRMS. α-Amylase inhibitory activities of these compounds were also investigated. The results showed that 6 compounds among them had good inhibitory activities compared with the positive control acarbose. Especially, 4-(2-(2-(6, 6-dimethyl-3-(4-methylbenzylidene))bicyclo[3.1.1]heptane-2-ylidene)indolyl-4-thiazol-4-yl)phenol (SZ14) exhibited remarkable α-amylase inhibitory activity with IC50 value of 4.11 μmol/L. From the structure-activity relationship, the structure of R2 gave great influence on the activities of thiazolyhydrazone derivatives. The kinetic inhibition study revealed that those 6 compounds were the noncompetitive inhibitor against α-amylase. It was used for molecular docking study to find out binding affinities for thiazolylhydrazone derivatives, and the binding mode of compound SZ14 with α-amylase was primarily investigated with molecular docking method.
2019, 39(5): 1383-1395
doi: 10.6023/cjoc201812038
Abstract:
Ester bonds are found widely in various fine chemicals, medicines, pesticides and functional materials. Despite the apparent simplicity, the construction of ester bonds often constitutes the most challenge in the synthesis of complex molecular containing ester functionality. Oxa-Michael addition represents an important class of organic reactions in carbon-heteroatom bond formation. The use of alcohol donors in oxa-Michael additions is well known. However, the use of carboxylic acid as the donor in the reaction is difficult due to the low activity of acid and a more pronounced reversibility of the reaction. To date, there is no general oxa-Michael addition of acids to α, β-unsaturated ketones reported. Herein, an efficient sodium carbonate promoted oxa-Michael addition of acids to α, β-unsaturated ketones to synthesize esters is reported. With a broad substrate scope, a well-common catalyst and simple operation, the approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of esters.
Ester bonds are found widely in various fine chemicals, medicines, pesticides and functional materials. Despite the apparent simplicity, the construction of ester bonds often constitutes the most challenge in the synthesis of complex molecular containing ester functionality. Oxa-Michael addition represents an important class of organic reactions in carbon-heteroatom bond formation. The use of alcohol donors in oxa-Michael additions is well known. However, the use of carboxylic acid as the donor in the reaction is difficult due to the low activity of acid and a more pronounced reversibility of the reaction. To date, there is no general oxa-Michael addition of acids to α, β-unsaturated ketones reported. Herein, an efficient sodium carbonate promoted oxa-Michael addition of acids to α, β-unsaturated ketones to synthesize esters is reported. With a broad substrate scope, a well-common catalyst and simple operation, the approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of esters.
2019, 39(5): 1396-1403
doi: 10.6023/cjoc201811039
Abstract:
The chlorination reaction of hydrazones with N-aryltrifluoroacetohydrazones by using trichloroisocyanuric acid as chlorine source was investigated, and a series of N-arylhydrazonyl chlorides and N-aryltrifluoroacetohydrazonyl chlorides were obtained in high yields. This method had advatages of easy operation, short reaction time, mild conditions and the use of stable and cheap chlorine source, which provides an efficiant method for the synthesis of N-arylhydrazonyl chlorides and N-aryltrifluoroacetohydrazonyl chlorides.
The chlorination reaction of hydrazones with N-aryltrifluoroacetohydrazones by using trichloroisocyanuric acid as chlorine source was investigated, and a series of N-arylhydrazonyl chlorides and N-aryltrifluoroacetohydrazonyl chlorides were obtained in high yields. This method had advatages of easy operation, short reaction time, mild conditions and the use of stable and cheap chlorine source, which provides an efficiant method for the synthesis of N-arylhydrazonyl chlorides and N-aryltrifluoroacetohydrazonyl chlorides.
2019, 39(5): 1404-1410
doi: 10.6023/cjoc201812035
Abstract:
An one-pot, cascade assembly of polysubstituted cyclopentene was realized via the N-heterocyclic carbene (NHC)-catalyzed annulation of the in situ activated α, β-unsaturated carboxylic acid with 2-(2-oxo-2-arylethyl)malononitrile through the sequence of Michael addition, aldol condesation and decarboxylation. This method could serve as a new attractive strategy for the practical syntheses of multi-functionalized cyclopentene derivatives with broad substrate scope, readily availability of starting materials, mild reaction conditions, excellent yields and operational simplicity.
An one-pot, cascade assembly of polysubstituted cyclopentene was realized via the N-heterocyclic carbene (NHC)-catalyzed annulation of the in situ activated α, β-unsaturated carboxylic acid with 2-(2-oxo-2-arylethyl)malononitrile through the sequence of Michael addition, aldol condesation and decarboxylation. This method could serve as a new attractive strategy for the practical syntheses of multi-functionalized cyclopentene derivatives with broad substrate scope, readily availability of starting materials, mild reaction conditions, excellent yields and operational simplicity.
2019, 39(5): 1411-1416
doi: 10.6023/cjoc201810010
Abstract:
The selective reduction of carbonyl group with organosilane as reducing agent was studied with methanol as a solvent under the action of 2.5 mol% C6H5BF3K and 2.2 epuiv. (EtO)3SiH. The target products were obtained in medium to high yield. This method shows good selectivity and provides a new method for carbonyl reduction.
The selective reduction of carbonyl group with organosilane as reducing agent was studied with methanol as a solvent under the action of 2.5 mol% C6H5BF3K and 2.2 epuiv. (EtO)3SiH. The target products were obtained in medium to high yield. This method shows good selectivity and provides a new method for carbonyl reduction.
2019, 39(5): 1417-1423
doi: 10.6023/cjoc201812006
Abstract:
An efficient palladium-catalyzed protocol for the synthesis of 4-bromoisoxazoles derivatives in moderate to good yields from readily available O-methyl oximes in basic ionic liquid has been developed. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. This cascade cyclization/bromination process provides a novel route for directly accessing 4-bromoisoxazole in good to excellent yields and good functional group tolerance with high atom efficiency. Notably, the current methodology could also be conveniently applied to the synthesis of isoxazoles naturally occurring biologically active frameworks.
An efficient palladium-catalyzed protocol for the synthesis of 4-bromoisoxazoles derivatives in moderate to good yields from readily available O-methyl oximes in basic ionic liquid has been developed. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. This cascade cyclization/bromination process provides a novel route for directly accessing 4-bromoisoxazole in good to excellent yields and good functional group tolerance with high atom efficiency. Notably, the current methodology could also be conveniently applied to the synthesis of isoxazoles naturally occurring biologically active frameworks.
2019, 39(5): 1436-1443
doi: 10.6023/cjoc201810016
Abstract:
Using carbazole as the donor motif, triazine as the acceptor motif, two thermally activated delayed fluorescence (TADF) molecules of m-CzTri and p-CzTri were designed and synthesized through efficient combination and position regulation. Both materials emit bright blue fluorescence with very small singlet-triplet splitting energy. Computational simulations show that the donor and acceptor groups are well separated from the highest occupied orbit (HOMO) and the lowest unoccupied orbit (LUMO). In addition, their thermal, electrochemical, photophysical, and device properties were tested. Among them, the color coordinates of organic light emitting diode (OLED) devices with m-CzTri as the emitter were (0.15, 0.25), and the external quantum efficiency was as high as 18%.
Using carbazole as the donor motif, triazine as the acceptor motif, two thermally activated delayed fluorescence (TADF) molecules of m-CzTri and p-CzTri were designed and synthesized through efficient combination and position regulation. Both materials emit bright blue fluorescence with very small singlet-triplet splitting energy. Computational simulations show that the donor and acceptor groups are well separated from the highest occupied orbit (HOMO) and the lowest unoccupied orbit (LUMO). In addition, their thermal, electrochemical, photophysical, and device properties were tested. Among them, the color coordinates of organic light emitting diode (OLED) devices with m-CzTri as the emitter were (0.15, 0.25), and the external quantum efficiency was as high as 18%.
2019, 39(5): 1450-1455
doi: 10.6023/cjoc201812014
Abstract:
Ruthenium acetylacetonate and aminophosphine ligand were selected as the catalyst system and applied to the catalytic hydrogenation of dimethyl malonate into methyl 3-hydroxypropanoate. With the focus on the catalytic efficiency, the important factors with significant influences on the dimethyl malonate conversion and methyl 3-hydroxypropanoate selectivity were well discussed, including the structure and dosage of the ligand, temperature, reaction time, solvent, and so on. The results revealed that catalyst system of ruthenium acetylacetonate and o-(diphenylphosphino)aniline ligand could obtain significant catalytic results. Under the optimal reaction conditions, this catalyst system can also be applied to catalytic hydrogenation of some other esters with high efficiency.
Ruthenium acetylacetonate and aminophosphine ligand were selected as the catalyst system and applied to the catalytic hydrogenation of dimethyl malonate into methyl 3-hydroxypropanoate. With the focus on the catalytic efficiency, the important factors with significant influences on the dimethyl malonate conversion and methyl 3-hydroxypropanoate selectivity were well discussed, including the structure and dosage of the ligand, temperature, reaction time, solvent, and so on. The results revealed that catalyst system of ruthenium acetylacetonate and o-(diphenylphosphino)aniline ligand could obtain significant catalytic results. Under the optimal reaction conditions, this catalyst system can also be applied to catalytic hydrogenation of some other esters with high efficiency.
2019, 39(5): 1456-1459
doi: 10.6023/cjoc201810029
Abstract:
Most small chiral molecule catalysts are suffered from a rigid process in both product separation and recovery. Therefore more attention has been drawn to the soluble polymer-supported catalyst which could be easily recycled. In this paper, a new type of reusable chiral binaphthol polymer-supported diethylzinc catalyst was synthesized and applied in the asymmetric epoxidation of (E)-α, β-unsaturated aryl ketones. The scope of this reaction was explored. Various (E)-α, β-aryl ketones could be easily prepared in good yield (up to 88%) and high ee value (up to 94%) via this asymmetric epoxidation process. Ligands were recovered to explore the inductive effect of the reaction. Recovery experiments of this binaphthol polymer-supported diethylzinc catalyst were conducted. The results indicate that the asymmetric induction ability of the reclaimed chiral polymer 1, 1'-bi-2-naphthol did not decrease significantly.
Most small chiral molecule catalysts are suffered from a rigid process in both product separation and recovery. Therefore more attention has been drawn to the soluble polymer-supported catalyst which could be easily recycled. In this paper, a new type of reusable chiral binaphthol polymer-supported diethylzinc catalyst was synthesized and applied in the asymmetric epoxidation of (E)-α, β-unsaturated aryl ketones. The scope of this reaction was explored. Various (E)-α, β-aryl ketones could be easily prepared in good yield (up to 88%) and high ee value (up to 94%) via this asymmetric epoxidation process. Ligands were recovered to explore the inductive effect of the reaction. Recovery experiments of this binaphthol polymer-supported diethylzinc catalyst were conducted. The results indicate that the asymmetric induction ability of the reclaimed chiral polymer 1, 1'-bi-2-naphthol did not decrease significantly.
2019, 39(5): 1460-1468
doi: 10.6023/cjoc201811040
Abstract:
In order to explore a new type of anti-diabetic molecules, dipeptide derivatives containing uracil structural units were designed. The key intermediate S-thymine-L-cysteine (IM-2) was obtained from uracil, paraformaldehyde and cysteine through two step reactions, and then 16 dipeptide derivatives were successfully synthesized through amino protection, carboxylation and amino acid coupling. All new compounds have been characterized by 1H NMR, 13C NMR and HRMS, and the peroxisome proliferator response element (PPRE) activated activity, α-glucosidase-rat inhibitory activity and dipeptidyl peptidase-4 (DPP-4) inhibitory activity were screened for all target molecules. The results showed that these molecules had weak above-mentioned activities, meanwhile the change trend of α-glucosidase-rat inhibitory activity of these molecules is opposite to that of PPRE agonistic activity and DPP-4 inhibitory activity. It maybe provides an idea for the research of designing novel polypeptide multi-target drugs.
In order to explore a new type of anti-diabetic molecules, dipeptide derivatives containing uracil structural units were designed. The key intermediate S-thymine-L-cysteine (IM-2) was obtained from uracil, paraformaldehyde and cysteine through two step reactions, and then 16 dipeptide derivatives were successfully synthesized through amino protection, carboxylation and amino acid coupling. All new compounds have been characterized by 1H NMR, 13C NMR and HRMS, and the peroxisome proliferator response element (PPRE) activated activity, α-glucosidase-rat inhibitory activity and dipeptidyl peptidase-4 (DPP-4) inhibitory activity were screened for all target molecules. The results showed that these molecules had weak above-mentioned activities, meanwhile the change trend of α-glucosidase-rat inhibitory activity of these molecules is opposite to that of PPRE agonistic activity and DPP-4 inhibitory activity. It maybe provides an idea for the research of designing novel polypeptide multi-target drugs.
2019, 39(5): 1469-1474
doi: 10.6023/cjoc201812046
Abstract:
Zinc-proline complex catalyzed Knoevenagel condensation in water was reported. Seventeen aldehydes and two ketones were investigated, which coupled with malononitrile smoothly affording desired Knoevenagel condensation products in 5~10 min at 80℃ in the yields of 84%~99%. The catalyst can be recovered and reused for ten cycles without loss of activity.
Zinc-proline complex catalyzed Knoevenagel condensation in water was reported. Seventeen aldehydes and two ketones were investigated, which coupled with malononitrile smoothly affording desired Knoevenagel condensation products in 5~10 min at 80℃ in the yields of 84%~99%. The catalyst can be recovered and reused for ten cycles without loss of activity.
2019, 39(5): 1483-1488
doi: 10.6023/cjoc201811034
Abstract:
Hydrazine (N2H4) is a highly toxic biochemical reagent with the capability of mutagenic, teratogenic and carcinogenic. For accurately monitoring the concentration of N2H4 in the environment and life, two FRET (fluorescence resonance energy transfer)-based dual-emissive ratiometric fluorescent probes (FRET-1/2) were designed and synthesized. The structures of both probes were charactered by 1H NMR, 13C NMR and HRMS. The results prove that both probes exhibit good selectivity and sensitivity to N2H4 and can be used for detecting N2H4 in water samples.
Hydrazine (N2H4) is a highly toxic biochemical reagent with the capability of mutagenic, teratogenic and carcinogenic. For accurately monitoring the concentration of N2H4 in the environment and life, two FRET (fluorescence resonance energy transfer)-based dual-emissive ratiometric fluorescent probes (FRET-1/2) were designed and synthesized. The structures of both probes were charactered by 1H NMR, 13C NMR and HRMS. The results prove that both probes exhibit good selectivity and sensitivity to N2H4 and can be used for detecting N2H4 in water samples.
2019, 39(5): 1489-1496
doi: 10.6023/cjoc201810025
Abstract:
Based on the agrochemical structure of anthranilic diamides, fourteen novel N-substitutedphenyl-2-pyrazolyl- nicotinamides were conveniently synthesized with 2-chloro-3-cyanopyridine and 4-bromopyrazole or 3, 5-dimethylpyrazole as starting materials, via an "acyl transposing" design strategy. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The preliminary bioassay tests indicated that most of these compounds exhibited obvious insecticidal activity at the test concentration of 200 mg/L, among which N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)-2-(3, 5-dimethyl-1H-pyra- zol-1-yl)nicotinamide (Il) possessed a 70% mortality rate against Mythimna separata Walker; some of the compounds displayed favorable fungicidal activities at 50 mg/L towards Physalospora piricola and Alternaria solani Sorauer, especially 2-(4-bromo-1H-pyrazol-1-yl)-N-(2-(cyclopropylcarbamoyl)-4-iodo-6-methylphenyl)nicotinamide (If) and 2-(4-bromo-1H- pyrazol-1-yl)-N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)nicotinamide (Ih) against Physalospora piricola, and 2-(4- bromo-1H-pyrazol-1-yl)-N-(4-chloro-2-(propylcarbamoyl)phenyl)nicotinamide (Id) against Alternaria solani Sorauer had growth inhibitory rates of 62.9%, 54.3% and 54.5%, respectively. These research results provide important reference for the further study of novel 2-pyrazolylnicotinamide derivatives.
Based on the agrochemical structure of anthranilic diamides, fourteen novel N-substitutedphenyl-2-pyrazolyl- nicotinamides were conveniently synthesized with 2-chloro-3-cyanopyridine and 4-bromopyrazole or 3, 5-dimethylpyrazole as starting materials, via an "acyl transposing" design strategy. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The preliminary bioassay tests indicated that most of these compounds exhibited obvious insecticidal activity at the test concentration of 200 mg/L, among which N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)-2-(3, 5-dimethyl-1H-pyra- zol-1-yl)nicotinamide (Il) possessed a 70% mortality rate against Mythimna separata Walker; some of the compounds displayed favorable fungicidal activities at 50 mg/L towards Physalospora piricola and Alternaria solani Sorauer, especially 2-(4-bromo-1H-pyrazol-1-yl)-N-(2-(cyclopropylcarbamoyl)-4-iodo-6-methylphenyl)nicotinamide (If) and 2-(4-bromo-1H- pyrazol-1-yl)-N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)nicotinamide (Ih) against Physalospora piricola, and 2-(4- bromo-1H-pyrazol-1-yl)-N-(4-chloro-2-(propylcarbamoyl)phenyl)nicotinamide (Id) against Alternaria solani Sorauer had growth inhibitory rates of 62.9%, 54.3% and 54.5%, respectively. These research results provide important reference for the further study of novel 2-pyrazolylnicotinamide derivatives.
2019, 39(5): 1503-1508
doi: 10.6023/cjoc201811031
Abstract:
Hydrogen sulfide (H2S), the third gas signal molecule in mammals is studied more and more deeply, and great progress has been made on organic small molecule hydrogen sulfide donors. However, no hydrogen sulfide donor has been marketed as a drug yet. Metformin is a first-line drug for the treatment of diabetes. And some other biological activities such as anti-obesity, anticancer, and anti-aging have been disclosed in recent years. H2S donor has also shown promising prospect in antitumor, cardiovascular protection, anti-inflammation, ion channel regulation and anti-oxidation activities. In view of the potential of hydrogen sulfide and metformin for treatment of diseases, a novel hydrogen sulfide donor, metformin hydrosulfide, was thus designed. Till now, there is no report of this type of hydrogen sulfide donor. In our work, metformin hydrochloride was first basified to obtain metformin, followed by reaction with hydrogen sulfide to afford metformin hydrosulfide. The structure was fully characterized by 1H NMR, 13C NMR, elemental analysis and X-ray crystal. The content of hydrogen sulfide was determined by iodometry method, lead acetate test and methylene blue spectrophotometric method to be more than 96.00%. The metformin level was determined by high-pressure liquid chromatography (HPLC) to be more than 98.50%. The stability of metformin hydrosulfide was evaluated by iodometry method in solution and solid, respectively. The results indicate that metformin hydrosulfide is a promising new type of hydrogen sulfide donor which deserves further research and development.
Hydrogen sulfide (H2S), the third gas signal molecule in mammals is studied more and more deeply, and great progress has been made on organic small molecule hydrogen sulfide donors. However, no hydrogen sulfide donor has been marketed as a drug yet. Metformin is a first-line drug for the treatment of diabetes. And some other biological activities such as anti-obesity, anticancer, and anti-aging have been disclosed in recent years. H2S donor has also shown promising prospect in antitumor, cardiovascular protection, anti-inflammation, ion channel regulation and anti-oxidation activities. In view of the potential of hydrogen sulfide and metformin for treatment of diseases, a novel hydrogen sulfide donor, metformin hydrosulfide, was thus designed. Till now, there is no report of this type of hydrogen sulfide donor. In our work, metformin hydrochloride was first basified to obtain metformin, followed by reaction with hydrogen sulfide to afford metformin hydrosulfide. The structure was fully characterized by 1H NMR, 13C NMR, elemental analysis and X-ray crystal. The content of hydrogen sulfide was determined by iodometry method, lead acetate test and methylene blue spectrophotometric method to be more than 96.00%. The metformin level was determined by high-pressure liquid chromatography (HPLC) to be more than 98.50%. The stability of metformin hydrosulfide was evaluated by iodometry method in solution and solid, respectively. The results indicate that metformin hydrosulfide is a promising new type of hydrogen sulfide donor which deserves further research and development.
2019, 39(5): 1475-1478
doi: 10.6023/cjoc201812009
Abstract:
The chemical investigation of the broth extract of the endophytic fungus Phomopsis phyllanthicola A658, which was isolated from the medicinal plant Pogostemon cablin, resulted in the isolation of one new compound, named dothiorelone O (1) and one new natural product 2-(3, 5-dihydroxy-2-(7-hydroxyoctanoyl)phenyl)acetic acid (2), along with four known derivatives. Their structures were fully characterized by means of detailed spectroscopic analysis for new structures, and in comparison with published data for known compounds. Moreover, all of the compounds were evaluated for in vitro cytotoxic activities against SF-268, MCF-7, HepG-2, and A549 tumor cell lines.
The chemical investigation of the broth extract of the endophytic fungus Phomopsis phyllanthicola A658, which was isolated from the medicinal plant Pogostemon cablin, resulted in the isolation of one new compound, named dothiorelone O (1) and one new natural product 2-(3, 5-dihydroxy-2-(7-hydroxyoctanoyl)phenyl)acetic acid (2), along with four known derivatives. Their structures were fully characterized by means of detailed spectroscopic analysis for new structures, and in comparison with published data for known compounds. Moreover, all of the compounds were evaluated for in vitro cytotoxic activities against SF-268, MCF-7, HepG-2, and A549 tumor cell lines.
2019, 39(5): 1479-1482
doi: 10.6023/cjoc201812008
Abstract:
Two new isocoumarins derivatives, penicimarins J (1) and K (2), were isolated from the mangrove-derived fungus Penicillium citrinum HL-5126. Their structures were elucidated through extensive 1D NMR, 2D NMR and HR-ESI-MS spectroscopic analyses. The absolute configurations of 1 and 2 were determined by comparison of their circular dichroism (CD) spectra with the literature. Compounds 1 and 2 showed inhibitory activities against α-glucosidase with the IC50 values of 18.37 and 25.86 μg/mL, respectively.
Two new isocoumarins derivatives, penicimarins J (1) and K (2), were isolated from the mangrove-derived fungus Penicillium citrinum HL-5126. Their structures were elucidated through extensive 1D NMR, 2D NMR and HR-ESI-MS spectroscopic analyses. The absolute configurations of 1 and 2 were determined by comparison of their circular dichroism (CD) spectra with the literature. Compounds 1 and 2 showed inhibitory activities against α-glucosidase with the IC50 values of 18.37 and 25.86 μg/mL, respectively.
2019, 39(5): 1497-1502
doi: 10.6023/cjoc201811012
Abstract:
A series of aminoguanidine derivatives containing a biphenyl moiety were designed, synthesized, and characterized by spectra methods using chalcone-aminoguanidine derivative as the lead compound. The antibacterial activity of the target compounds was evaluated. The results indicated that most of the target compounds showed potent inhibitory activity with the minimum inhibitory concentration values (MICs) in range of 0.5~8 μg/mL. Among of which, 2-((4'-bromo-[1, 1'-biphenyl]-4-yl)methylene)hydrazine-1-carboximidamide (3j) exhibited broad-spectrum antibacterial activity, effective to all the chosen strains including two multidrug-resistant gram-positive strains, showed the most potent inhibitory against S. aureus CMCC(B) 26003, E. faecalis CMCC 29212 and multidrug-resistant S. aureus ATCC 33591 with a MIC value of 0.5 μg/mL. Moreover, low cytotoxicity of compound 3j (HEK 293T, IC50=60.90 µmol/L) was found. These results suggested that the Compound 3j, with high safety, was potential and valuable in the research of novel antibacterial drugs.
A series of aminoguanidine derivatives containing a biphenyl moiety were designed, synthesized, and characterized by spectra methods using chalcone-aminoguanidine derivative as the lead compound. The antibacterial activity of the target compounds was evaluated. The results indicated that most of the target compounds showed potent inhibitory activity with the minimum inhibitory concentration values (MICs) in range of 0.5~8 μg/mL. Among of which, 2-((4'-bromo-[1, 1'-biphenyl]-4-yl)methylene)hydrazine-1-carboximidamide (3j) exhibited broad-spectrum antibacterial activity, effective to all the chosen strains including two multidrug-resistant gram-positive strains, showed the most potent inhibitory against S. aureus CMCC(B) 26003, E. faecalis CMCC 29212 and multidrug-resistant S. aureus ATCC 33591 with a MIC value of 0.5 μg/mL. Moreover, low cytotoxicity of compound 3j (HEK 293T, IC50=60.90 µmol/L) was found. These results suggested that the Compound 3j, with high safety, was potential and valuable in the research of novel antibacterial drugs.
