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Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China
* Author to whom correspondence should be addressed.
Received: 23 August 2010; in revised form: 10 November 2010 / Accepted: 30 November 2010 / Published: 9 December 2010
Abstract: Starting from 4-chlorobenzoic acid, 10 new 5-(4-chlorophenyl)-N-substituted-N-1,3,4-thiadiazole-2-sulfonamide derivatives were synthesized in six-steps. Esterification of 4-chlorobenzoic acid with methanol and subsequent hydrazination, salt formation and cyclization afforded 5-(4-chlorophen-yl)-1,3,4-thiadiazole-2-thiol (5). Conversion of this intermediate into sulfonyl chloride 6, followed by nucleophilic attack of the amines gave the title sulfonamides 7a-7j whose structures were confirmed by NMR, IR and elemental analysis. The bioassay tests showed that compounds 7b and 7i possessed certain anti-tobacco mosaic virus activity.
Keywords: sulfonamide derivatives; 1,3,4-thiadiazole moiety; synthesis; antiviral activity
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MDPI and ACS Style
Chen, Z.; Xu, W.; Liu, K.; Yang, S.; Fan, H.; Bhadury, P.S.; Huang, D.-Y.; Zhang, Y. Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides. Molecules 2010, 15, 9046-9056.
Chen Z, Xu W, Liu K, Yang S, Fan H, Bhadury PS, Huang D-Y, Zhang Y. Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides. Molecules. 2010; 15(12):9046-9056.
Chen, Zhuo; Xu, Weiming; Liu, Keming; Yang, Song; Fan, Huitao; Bhadury, Pinaki S.; Huang, De-Yu; Zhang, Yuping. 2010. "Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides." Molecules 15, no. 12: 9046-9056.