Issue 5, 2015

Design, facile synthesis and anthelmintic activity of new O-substituted 6-methoxybenzothiazole-2-carbamates

Abstract

A series of new substituted 6-methoxybenzothiazoles was synthesized and evaluated for their anthelmintic activity. The synthesis of the desired compounds was achieved through the key intermediate 2-(2-aminobenzothiazol-6-yloxy)acetohydrazide6. Target compounds were designed to comprise diverse substitutions at the 6-position of the benzothiazole ring varying between the flexibility of a long aliphatic chain and the rigidity of some substituted heterocyclic rings. The in vitro paramphistomicidal activity of 15 of the synthesized compounds was assessed. N-[6-((4-Acetyl-5-(4-chlorophenyl) and (4-nitrophenyl)-4,5-dihydro-[1,3,4]-oxadiazol-2-yl(methoxy)benzothiazol-2-yl]acetamides (32, 33) were considerably active against rumen flukes. The impact of structural substitution on activity was examined. A computational study of the impact of the polar nature and hydrophilic–lipophilic properties was undertaken. An expanded structure–activity relationship (SAR) assessment of the different novel series is also discussed.

Graphical abstract: Design, facile synthesis and anthelmintic activity of new O-substituted 6-methoxybenzothiazole-2-carbamates

Article information

Article type
Concise Article
Submitted
12 Dec 2014
Accepted
25 Jan 2015
First published
27 Jan 2015

Med. Chem. Commun., 2015,6, 795-805

Design, facile synthesis and anthelmintic activity of new O-substituted 6-methoxybenzothiazole-2-carbamates

A. M. M. E. Omar, O. M. Aboulwafa, D. A. E. Issa, M. M. S. El-Shokrofy, M. E. Amr and I. M. El-Ashmawy, Med. Chem. Commun., 2015, 6, 795 DOI: 10.1039/C4MD00557K

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