New hydrazides and thiosemicarbazides derived from ethylenedioxythiophene as potential anticonvulsants

Abstract

A series of ethyl 7-({2-[(substituted)carbonyl]hydrazino}carbonyl)-2,3- dihydrothieno [3,4-b][1,4]dioxine-5-carboxylates (5-13) and ethyl 7-{[({2-[(substituted)carbonyl]hydra-zino}carbonothioyl)amino]carbonyl}-2, 3-dihydrothieno[3,4-b][1,4]dioxine-5-carboxy-lates (15-20) were synthesized in good yield by condensing ethyl-7-(chlorocarbonyl)-2,3-dihydrothieno[3,4-b][1,4] dioxine-5-carboxylate (4) with suitable hydrazides. The newly synthesized compounds were characterized using FTIR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analyses. The anticonvulsant activity of all the title compounds was investigated against maximal electroshock-induced seizures (MES) and pentylenetetrazole (PTZ)-induced convulsion models. None of the compounds showed toxicity at the maximum dose of 2000 mg/kg. Almost all the compounds showed protection in flexion and extension stage against induced convulsion. Among them, naphthyloxy-substituted derivatives exhibited very good response against induced seizures. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright © Taylor & Francis Group, LLC.