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.
Author(s)
Doaa A. E. Issa
Coauthor(s)
A. Mohsen M. E. Omar, Omaima M. Aboulwafa, May M. S. El-Shokrofy, May E. Amra and Ibrahim M. El-Ashmawy
Journal/Conference Information
Official journal of the European Federation for Medicinal Chemistry ,Volume 6, 795-805 DOI: 10.1039/C4MD00557K