Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides

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,...

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Autores principales: Chen, Zhuo, Xu, Weiming, Liu, Keming, Yang, Song, Fan, Huitao, Bhadury, Pinaki S., Hu, De-Yu, Zhang, Yuping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259578/
https://www.ncbi.nlm.nih.gov/pubmed/21150824
http://dx.doi.org/10.3390/molecules15129046
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author Chen, Zhuo
Xu, Weiming
Liu, Keming
Yang, Song
Fan, Huitao
Bhadury, Pinaki S.
Hu, De-Yu
Zhang, Yuping
author_facet Chen, Zhuo
Xu, Weiming
Liu, Keming
Yang, Song
Fan, Huitao
Bhadury, Pinaki S.
Hu, De-Yu
Zhang, Yuping
author_sort Chen, Zhuo
collection PubMed
description 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.
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spelling pubmed-62595782018-12-06 Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides Chen, Zhuo Xu, Weiming Liu, Keming Yang, Song Fan, Huitao Bhadury, Pinaki S. Hu, De-Yu Zhang, Yuping Molecules Article 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. MDPI 2010-12-09 /pmc/articles/PMC6259578/ /pubmed/21150824 http://dx.doi.org/10.3390/molecules15129046 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Chen, Zhuo
Xu, Weiming
Liu, Keming
Yang, Song
Fan, Huitao
Bhadury, Pinaki S.
Hu, De-Yu
Zhang, Yuping
Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides
title Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides
title_full Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides
title_fullStr Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides
title_full_unstemmed Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides
title_short Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides
title_sort synthesis and antiviral activity of 5‑(4‑chlorophenyl)-1,3,4-thiadiazole sulfonamides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259578/
https://www.ncbi.nlm.nih.gov/pubmed/21150824
http://dx.doi.org/10.3390/molecules15129046
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