title: Synthesis and antiviral activity of 5‑(4‑chlorophenyl)-1,3,4-thiadiazole sulfonamides.
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.
authors.affiliation: 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. gychecnzhuo@yahoo.com.cn
authors.forename: Zhuo
authors.initials: Z
authors.lastname: Chen
authors.forename: Weiming
authors.initials: W
authors.lastname: Xu
authors.forename: Keming
authors.initials: K
authors.lastname: Liu
authors.forename: Song
authors.initials: S
authors.lastname: Yang
authors.forename: Huitao
authors.initials: H
authors.lastname: Fan
authors.forename: Pinaki S
authors.initials: PS
authors.lastname: Bhadury
authors.forename: De-Yu
authors.initials: DY
authors.lastname: Hu
authors.forename: Yuping
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014026:Nicotiana / Q000821:virology*; D014027:Tobacco Mosaic Virus
chemical_list: D000998:Antiviral Agents; D013449:Sulfonamides