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.
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