synthesis and antiviral activity of 5？(4？chlorophenyl)-1,3,4-thiadiazole sulfonamides5的合成和抗病毒活性(4 chlorophenyl)1,3,4-thiadiazole磺胺类药.pdf

Molecules 2010, 15, 9046-9056; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and Antiviral Activity of 5-(4-Chlorophenyl)-1,3,4- Thiadiazole Sulfonamides Zhuo Chen, Weiming Xu, Keming Liu, Song Yang *, Huitao Fan, Pinaki S. Bhadury, De-Yu Hu * and Yuping Zhang 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; E-Mails: gychecnzhuo@ (Z.C.); xuweiming2009@163.com (W.X.); lkmingsd@126.com (K.L.); fanhuitao0818@163.com (H.F.); bhadury@ (P.S.B.); zhangyupinggz@163.com (Y.Z.) * Authors to whom correspondence should be addressed; E-Mails: gdjhzx@ (S.Y.); fcc.dyhu@ (D.-Y.H.); Tel.: +86 (851) 829 2170; Fax: +86 (851) 362 2211. 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