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]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
2. [2]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
7. [7]
  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
8. [8]
  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
9. [9]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
10. [10]
  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
11. [11]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
12. [12]
  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
13. [13]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
18. [18]
  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
19. [19]
  Xinzhe HUANG , Lihui XU , Yue YANG , Liming WANG , Zhangyong LIU , Zhongjian WANG . Preparation and visible light responsive photocatalytic properties of BiSbO₄/BiOBr. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 284-292. doi: 10.11862/CJIC.20240212
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(541)
HTML views(39)

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