Citation: Chun-Nong WANG, Tai-Ning ZENG, Sheng-Nan LI, Wan LI, Long-Fei LI, Fei CAO, Zi-Hui YANG. Preparation, Crystal Structure and Fungicidal Activity of N-(5-(benzofuranol-7-oxymethyl)-1, 3, 4-thiadiazol-2-yl)amide Compounds[J]. Chinese Journal of Structural Chemistry, ;2022, 41(3): 220321. doi: 10.14102/j.cnki.0254-5861.2011-3326 shu

Preparation, Crystal Structure and Fungicidal Activity of N-(5-(benzofuranol-7-oxymethyl)-1, 3, 4-thiadiazol-2-yl)amide Compounds

Chun-Nong WANG ^{a, †} ,
Tai-Ning ZENG ^{a, †} ,
Sheng-Nan LI ^a ,
Wan LI ^a,, ,
Long-Fei LI ^a ,
Fei CAO ^a ,
Zi-Hui YANG ^b

a.
College of Pharmaceutical Sciences, Key Laboratory of Analytical Science and Technology of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, Baoding 071002, China
b.
Shan Dong Jinhuahai Biotechnology Co., Ltd Jinan 251400, China

Corresponding author: Wan LI, liwanjingmin@163.com
Received Date: 17 June 2021
Accepted Date: 16 October 2021

Fund Project: the Scientific Research Foundation of Hebei Educational Committee QN2019058Natural Science Foundation of Hebei Province of China H2021201059

Figures(6)

A variety of new N-(5-(benzofuranol-7-oxymethyl)-1, 3, 4-thiadiazol-2-yl)amide compounds (8a-i) were synthesized through four steps from benzofuranol as raw materials. The crystal structure of compound 8a (C₁₇H₂₁N₃O₃S, M_r = 347.43) was measured by X-ray diffraction, which was classified as monoclinic system, Z = 4, V = 1742.72(8) Å³, D_c = 1.324 Mg/m³, F(000) = 736, S = 1.03, μ = 0.21 mm^-1, space group P2₁ with a = 9.9177(3), b = 8.9519(2), c = 19.8679(5) Å, the final R = 0.035 and wR = 0.105 for 3873 observed reflections (I > 2σ(I)). The X-ray structure presented N(3)–H(3)···N(2) and C(6)–H(6)···O(3) intermolecular hydrogen bonds, which acted as an important role in stabilizing the crystal structure. Additionally, preliminary biological assay on compound 8a showed good fungicidal activity in vivo, with the inhibition of 75% against Pseudoperonospora cubensis at 200 mg/L.
- N-(5-(benzofuranol-7-oxymethyl)-1,3,4-thiadiazol-2-yl)amide,
- preparation,
- crystal structure,
- antifungal activity
1. [1]
  Richardson, S. N.; Nsiama, T. K.; Walker, A. K.; McMullin, D. R.; Miller, J. D. Antimicrobial dihydrobenzofurans and xanthenes from a foliar endophyte of Pinus strobus. Phytochemistry 2015, 117, 436–443. doi: 10.1016/j.phytochem.2015.07.009
2. [2]
  Bernal, F. A.; Gerhards, M.; Kaiser, M.; Wünsch, B.; Schmidt, T. J. (±)-trans-2-phenyl-2, 3-dihydrobenzofurans as leishmanicidal agents: synthesis, in vitro evaluation and SAR analysis. Eur. J. Med. Chem. 2020, 205, 112493. doi: 10.1016/j.ejmech.2020.112493
3. [3]
  Miert, S. V.; Dyck, S. V.; Schmidt, T. J.; Brun, R.; Vlietinck, A.; Lemière, G.; Pieters, L. Antileishmanial activity, cytotoxicity and QSAR analysis of synthetic dihydrobenzofuran lignans and related benzofurans. Bioorg. Med. Chem. 2005, 13, 661–669. doi: 10.1016/j.bmc.2004.10.058
4. [4]
  Masi, M.; Cimmino, A.; Boari, A.; Tuzi, A.; Zonno, M. C.; Baroncelli, R.; Vurro, M.; Evidente, A. Colletochlorins E and F, new phytotoxic tetrasubstituted pyran-2-one and dihydrobenzofuran, isolated from colletotrichum higginsianum with potential herbicidal activity. J. Agric. Food Chem. 2017, 65, 1124–1130. doi: 10.1021/acs.jafc.6b05193
5. [5]
  Lin, D.; Xiao, M. W.; Yang, Z. H.; Li, B. B.; Hu, A. X.; Ye, J. Synthesis and herbicidal activity of N-(2, 2-dimethyl-7-alkoxy-2, 3-dihydrobenzofu-ran-5-yl)-2-(4-arylxoyphenoxy) propionamides. Chem. Res. Chin. U. 2017, 33, 74–79. doi: 10.1007/s40242-016-6305-1
6. [6]
  Baldin, E. L. L.; Dias, H. J.; Souza, C. M. D.; Soares, M. C. E.; Grundman, C. O.; Santos, T. L. B.; Crotti, A. E. M. Insecticidal and inhibitory effects of dihydrobenzofuran neolignans on Bemisia tabaci. J. Pest. Sci. 2019, 92, 861–869. doi: 10.1007/s10340-018-1053-2
7. [7]
  Li, W.; Yang, Z. H.; Hu, A. X.; Ye, J.; Ou, X. M.; Pei, H.; He, L.; Li, J. M. Synthesis and fungicidal activities of 2-{[(2-(1H -1, 2, 4-triazol-1-yl)-ethylidene)amino]oxy}alkanamides containing dihydrobenzofuran. Heterocycl. Commun. 2018, 24, 339–344. doi: 10.1515/hc-2017-0245
8. [8]
  Muğlu, H.; Şener, N.; Mohammad Emsaed, H. A.; Özkınalı, S.; Özkan, O. E.; Gür, M. Synthesis and characterization of 1, 3, 4-thiadiazole compounds derived from 4-phenoxybutyric acid for antimicrobial activities. J. Mol. Struct. 2018, 1174, 151–159. doi: 10.1016/j.molstruc.2018.03.116
9. [9]
  Sekhar, M. M.; Nagarjuna, U.; Padmavathi, V.; Padmaja, A.; Reddy, N. V.; Vijaya, T. Synthesis and antimicrobial activity of pyrimidinyl 1, 3, 4-oxadiazoles, 1, 3, 4-thiadiazoles and 1, 2, 4-triazoles. Eur. J. Med. Chem. 2018, 145, 1–10. doi: 10.1016/j.ejmech.2017.12.067
10. [10]
  Gür, M.; Şener, N.; Muğlu, H.; Çavuş, M. S.; Özkan, O. E.; Kandemirli, F.; Şener, İ. New 1, 3, 4-thiadiazole compounds including pyrazine moiety: synthesis, structural properties and antimicrobial features. J. Mol. Struct. 2017, 1139, 111–118. doi: 10.1016/j.molstruc.2017.03.019
11. [11]
  Güzeldemirci, N. U.; Küçükbasmacı, Ö. Synthesis and antimicrobial activity evaluation of new 1, 2, 4-triazoles and 1, 3, 4-thiadiazoles bearing imidazo[2, 1-b]thiazole moiety. Eur. J. Med. Chem. 2010, 45, 63–68. doi: 10.1016/j.ejmech.2009.09.024
12. [12]
  Foroumadi, A.; Rineh, A.; Emami, S.; Siavoshi, F.; Massarrat, S.; Safari, F.; Rajabalian, S.; Falahati, M.; Lotfali, E.; Shafiee, A. Synthesis and anti-Helicobacter pylori activity of 5-(nitroaryl)-1, 3, 4-thiadiazoles with certain sulfur containing alkyl side chain. Bioorg. Med. Chem. Lett. 2008, 18, 3315–3320. doi: 10.1016/j.bmcl.2008.04.033
13. [13]
  Luo, Y.; Zhang, S.; Liu, Z. J.; Chen, W.; Fu, J.; Zeng, Q. F.; Zhu, H. L. Synthesis and antimicrobical evaluation of a novel class of 1, 3, 4-thiadiazole: derivatives bearing 1, 2, 4-triazolo[1, 5-a]pyrimidine moiety. Eur. J. Med. Chem. 2013, 64, 54–61. doi: 10.1016/j.ejmech.2013.04.014
14. [14]
  Serban, G. 2-Amino-1, 3, 4-thiadiazoles as prospective agents in trypanosomiasis and other parasitoses. Acta Pharm. 2020, 70, 259–290. doi: 10.2478/acph-2020-0031
15. [15]
  Freitas, R. H. C. N.; Barbosa, J. M. C.; Bernardino, P.; Sueth-Santiago, V.; Wardell, S. M. S. V.; Wardell, J. L.; Decoté-Ricardo, D.; Melo, T. G.; da Silva, E. F.; Salomão, K.; Fraga, C. A. M. Synthesis and trypanocidal activity of novel pyridinyl-1, 3, 4-thiadiazole derivatives. Biomed. Pharmacother. 2020, 127, 110162. doi: 10.1016/j.biopha.2020.110162
16. [16]
  Mojallal-Tabatabaei, Z.; Foroumadi, P.; Toolabi, M.; Goli, F.; Moghimi, S.; Kaboudanian-Ardestani, S.; Foroumadi, A. 2-(Bipiperidin-1-yl)-5-(nitroaryl)-1, 3, 4-thiadiazoles: synthesis, evaluation of in vitro leishmanicidal activity, and mechanism of action. Bioorg. Med. Chem. 2019, 27, 3682–3691. doi: 10.1016/j.bmc.2019.07.009
17. [17]
  Lv, M.; Liu, G.; Jia, M.; Xu, H. Synthesis of matrinic amide derivatives containing 1, 3, 4-thiadiazole scaffold as insecticidal/acaricidal agents. Bioorg. Chem. 2018, 81, 88–92. doi: 10.1016/j.bioorg.2018.07.034
18. [18]
  Al-Qahtani, A.; Siddiqui, Y. M.; Bekhit, A. A.; El-Sayed, O. A.; Aboul-Enein, H. Y.; Al-Ahdal, M. N. Inhibition of growth of Leishmania donovani promastigotes by newly synthesized 1, 3, 4-thiadiazole analogs. Saudi. Pharm. J. 2009, 17, 227–232. doi: 10.1016/j.jsps.2009.08.005
19. [19]
  Pal, S.; Singh, V.; Kumar, R.; Gogoi, R. Design and development of 1, 3, 4-thiadiazole based potent new nano-fungicides. J. Mol. Struct. 2020, 1219, 128507. doi: 10.1016/j.molstruc.2020.128507
20. [20]
  Omar, Y. M.; Abdel-Moty, S. G.; Abdu-Allah, H. H. M. Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1, 3, 4-thiadiazole-thiazolidinone hybrids: the contribution of the substituents at 5th positions is size dependent. Bioorg Chem. 2020, 97, 103657. doi: 10.1016/j.bioorg.2020.103657
21. [21]
  Shen, F.; Hu, A. X.; Luo, X. F.; Ye, J.; Ou, X. M. Synthesis and bioactivity of (E)-2-benzylidenimino-4-(7-methoxy-2, 2-dimethyl-2, 3-dihydroben-zofuran-5-y1) thiazole. Chin. J. Org. Chem. 2012, 32, 388–392. doi: 10.6023/cjoc1108151
22. [22]
  Zou, X. J.; Jin, G. Y.; Zhang, Z. X. Synthesis, fungicidal activity, and QSAR of pyridazinonethiadiazoles. J. Agric. Food Chem. 2002, 50, 1451−1454. doi: 10.1021/jf0109266
23. [23]
  Chen, H.; Li, Z.; Han, Y. Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl(alkylthio)-5-pyrazolyl-1, 3, 4-oxadiazoles (thiadiazoles). J. Agric. Food Chem. 2000, 48, 5312−5315. doi: 10.1021/jf991065s
24. [24]
  Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Cryst. 2015, C71, 3–8.
1. [1]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
2. [2]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
3. [3]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
4. [4]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
5. [5]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
6. [6]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
7. [7]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
8. [8]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
9. [9]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
10. [10]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
11. [11]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
12. [12]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
13. [13]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
14. [14]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
15. [15]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
16. [16]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2023.100416
17. [17]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
18. [18]
  Jun LI , Huipeng LI , Hua ZHAO , Qinlong LIU . Preparation and photocatalytic performance of AgNi bimetallic modified polyhedral bismuth vanadate. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 601-612. doi: 10.11862/CJIC.20230401
19. [19]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
20. [20]
  Jia Fu , Shilong Zhang , Lirong Liang , Chunyu Du , Zhenqiang Ye , Guangming Chen . PEDOT-based thermoelectric composites: Preparation, mechanism and applications. Chinese Chemical Letters, 2024, 35(9): 109804-. doi: 10.1016/j.cclet.2024.109804

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(384)
HTML views(30)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142