Design, Synthesis and Fungicidal Bioactivity of 1, 2, 4-Triazoles or Thiadiazoles Containing a Benzenesulfonamide Moiety
- Corresponding author: LI Zhengming, nkzml@vip.163.com
Citation:
CHEN Minggui, HUA Xuewen, Wei WEI, ZHANG Dongkai, LIU Ming, WU Changchun, ZHOU Sha, LI Yuxin, WANG Baolei, ZHOU Sha, LI Zhengming. Design, Synthesis and Fungicidal Bioactivity of 1, 2, 4-Triazoles or Thiadiazoles Containing a Benzenesulfonamide Moiety[J]. Chinese Journal of Applied Chemistry,
;2017, 34(10): 1161-1171.
doi:
10.11944/j.issn.1000-0518.2017.10.170163
Lin L S, Lanza T J, Castonguay L A. Bioisosteric Replacement of Anilide with Benzoxazole:Potent and Orally Bioavailable Antagonists of VLA-4[J]. Bioorg Med Chem Lett, 2004,14(9):2331-2334. doi: 10.1016/j.bmcl.2004.01.098
Chandrakantha B, Shetty P, Nambiyar V. Synthesis, Characterization and Biological Activity of Some New 1, 3, 4-Oxadiazole Bearing 2-Flouro-4-methoxy Phenyl Moiety[J]. Eur J Med Chem, 2010,45(3):1206-1210. doi: 10.1016/j.ejmech.2009.11.046
Gouda M A, Berghot M A, El-Ghani G E A. ChemInform Abstract:Synthesis and Antimicrobial Activities of Some New Thiazole and Pyrazole Derivatives Based on 4, 5, 6, 7-Tetrahydrobenzothiophene Moiety[J]. Eur J Med Chem, 2010,45(4):1338-1345. doi: 10.1016/j.ejmech.2009.12.020
He S C, Jeyakkumar P, Srinivasarao A. Recent Advance in Sulfonamide-based Medicinal Chemistry[J]. Sci Sin Chim, 2016,46(9):823-847. doi: 10.1360/N032016-00029
Sunil D, Isloor A M, Shetty P. 6-[3-(4-Fluorophenyl)-1H-pyrazol-4-yl]-3-[(2-naphthyloxy)methyl] [1, 2, 4] triazolo[3, 4-b] [1, 3, 4] thiadiazole as a Potent Antioxidant and an Anticancer Agent Induces Growth Inhibition Followed by Apoptosis in HepG2 Cells[J]. Arab J Chem, 2010,3(4):211-217. doi: 10.1016/j.arabjc.2010.06.002
Chowrasia D, Karthikeyan C, Choure L. Synthesis, Characterization and Anti Cancer Activity of Some Fluorinated 3, 6-Diaryl-[1, 2, 4] triazolo[3, 4-b] [1, 3, 4] thiadiazoles[J]. Arab J Chem, 2017,10(S2):S2424-S2428.
Dai H, Li G, Chen J. Synthesis and Biological Activities of Novel 1, 3, 4-Thiadiazole-containing Pyrazole Oxime Derivatives[J]. Bioorg Med Chem Lett, 2016,26(15):3818-3821. doi: 10.1016/j.bmcl.2016.04.094
Li Z S, Wang W M, Lu W. Synthesis and Biological Evaluation of Nonsymmetrical Aromatic Disulfides as Novel Inhibitors of Acetohydroxyacid Synthase[J]. Bioorg Med Chem Lett, 2013,23(13):3723-3727. doi: 10.1016/j.bmcl.2013.05.013
Wang T, Miao W, Wu S. Synthesis, Crystal Structure, and Herbicidal Activities of 2-Cyanoacrylates Containing 1, 3, 4-Thiadiazole Moieties[J]. Chinese J Chem, 2011,29(29):959-967.
YANG Huazheng, ZOU Xiaomao, ZHU Youquan, et al, Modern Pesticide Chemistry[M]. Beijing:Chemical Industry Press, 2013(in Chinese).
Essghaier B, Naouar A, Abdelhak J. Synthesis, Crystal Structure and Potential Antimicrobial Activities of Di(4-sulfamoyl-phenyl-ammonium) Sulphate[J]. Microbiol Res, 2014,169(7/8):504-510.
Jaiswal M, Khadikar P V, Supuran C T. Topological Modeling of Lipophilicity, Diuretic Activity, and Carbonic Inhibition Activity of Benzene Sulfonamides:A Molecular Connectivity Approach[J]. Bioorg Med Chem Lett, 2004,14(22):5661-5666. doi: 10.1016/j.bmcl.2004.08.051
Navarrete-Vázquez G, Morales-Vilchis M G, Estrada-Soto S. Synthesis of 2-{2-[(α/β-Naphthalen-1-ylsulfonyl)amino]-1, 3-thiazol-4-yl Acetamides with 11β-Hydroxysteroid Dehydrogenase Inhibition and in Combo Antidiabetic Activities[J]. Eur J Med Chem, 2014,74C:179-186.
Xie Y, Chi H W, Guan A Y. Synthesis and Evaluation of Substituted 3-(Pyridin-2-yl)benzenesulfonamide Derivatives as Potent Herbicidal Agents[J]. Bioorg Med Chem, 2016,24(3):428-434. doi: 10.1016/j.bmc.2015.08.037
Xu H, Zhang L, Su B F. Natural Products-Based Insecticidal Agents 1.Semi-Synthesis and Insecticidal Activity of 4β-Benzenesulfonamide Derivatives of Podophyllotoxin Against Mythimna Separata Walker[J]. Heterocycles, 2009,77(1):293-300. doi: 10.3987/COM-08-S(F)14
Sonara S, Vaidyab S, Bagalb M. Synthesis and Characterization of Schiff Base Ligands and Antimicrobial Activity[J]. Adv Appl Sci Res, 2016,7(1):13-16.
SUN Wenyue. Flusulfamide-A Novel Soil Fungicide[J]. World Pestic, 1995(5):60-61.
Wang B L, Shi Y X, Zhang S J. Syntheses, Biological Activities and SAR Studies of Novel Carboxamide Compounds Containing Piperazine and Arylsulfonyl Moieties[J]. Eur J Med Chem, 2016,117:167-178. doi: 10.1016/j.ejmech.2016.04.005
Hua X W, Zhou S, Chen M G. Design, Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Tetrahydrophthalimide Substructure[J]. Chem Res Chinese Univ, 2016,32(3):396-401. doi: 10.1007/s40242-016-5480-4
Sławiński J, Pogorzelska A, ołnowska B. Carbonic Anhydrase Inhibitors. Synthesis of a Novel Series of 5-Substituted 2, 4-Dichlorobenzenesulfonamides and Their Inhibition of Human Cytosolic Isozymes Ⅰ and Ⅱ and the Transmembrane Tumor-associated Isozymes Ⅸ and Ⅻ[J]. Eur J Med Chem, 2014,82:47-55. doi: 10.1016/j.ejmech.2014.05.039
Yadagiri B, Holagunda U D, Bantu R. Rational Design, Synthesis and Anti-proliferative Evaluation of Novel Benzosuberone Tethered with Hydrazide-hydrazones[J]. Bioorg Med Chem Lett, 2014,24(21):5041-5044. doi: 10.1016/j.bmcl.2014.09.018
Wang H, Zhu W, Yu Z. Synthesis and Structure Characterization of Sulfur Ethers Containing 1, 2, 4-Triazole and 1, 3, 4-Oxadiazole[J]. Chinese J Org Chem, 2012,32(10):1888-1893. doi: 10.6023/cjoc1202201
Abuo-Rahma E D A A, Abdel-Aziz M, Beshr E A M. 1, 2, 4-Triazole/oxime Hybrids as New Strategy for Nitric Oxide Donors:Synthesis, Anti-inflammatory, Ulceroginicity and Antiproliferative Activities[J]. Eur J Med Chem, 2013,71(4):185-198.
Pokuri S, Singla R K, Bhat V G. Insights on the Antioxidant Potential of 1, 2, 4-Triazoles:Synthesis, Screening & QSAR Studies[J]. Curr Drug Metab, 2014,15(4):389-397. doi: 10.2174/1389200215666140908101958
Zhang D K, Hua X W, Liu M. Design, Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Triazole and Oxadiazole Moieties[J]. Chem Res Chinese Univ, 2016,32(4):607-614. doi: 10.1007/s40242-016-6029-2
Chen W, Wei W, Zhou S. Design, Synthesis and Biological Activity of Novel Sulfonylurea Derivatives Containing Phenyl-substituted Pyrimidine Moiety[J]. Chem J Chinese Univ, 2015,36:672-681.
Chandna N, Chandak N, Kumar P. Metal and Solvent Free Synthesis of N-Sulfonylformamidines[J]. Green Chem, 2013,15(8):2294-2301. doi: 10.1039/c3gc40797g
Wei W, Cheng D D, Chen W. Design, Syntheses and Biological Activities of Novel Sulfonylureas Containing an Oxime Ether Moiety[J]. Chem Res Chinese Univ, 2016,32(2):1-7.
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