کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1393237 | 1501195 | 2009 | 9 صفحه PDF | دانلود رایگان |
Thirty nine new 3,4-di(substituted)oxy-N2,N5-bis(substituted)thiophene-2,5-dicarbohydrazides were synthesized starting from ethyl thiodiglycolate through multi-step reactions. In the synthetic sequence, 3,4-dihydroxythiophene-2,5-diester (1) was obtained by condensing the ethyl thiodiglycolate with diethyl oxalate. It was derivatized using different alkyl halides to give disubstituted thiophene esters (2–5), which were then converted to corresponding hydrazides (6–9) following usual methods. Finally, these hydrazides, on treatment with various substituted carbonyl compounds underwent smooth condensation to yield target hydrazones (10–13). The new compounds were characterized using FT-IR, 1H NMR and 13C NMR, mass spectral and elemental analyses. The anticonvulsant activity of the title compounds was established after intraperitoneal (ip) administration in three seizure models, which include maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) and 6 Hz screens and their neurotoxicity was also evaluated. Compound 11f has emerged as an active compound with no neurotoxicity in this series. Also, the structure–activity relationship of the tested compounds was discussed.
Thirty-nine new 3,4-di(substituted)oxy-N2,N5-bis(substituted)thiophene-2,5-dicarbohydrazides (10a–r, 11a–j, 12a–e and 13a–f) were synthesized and evaluated for their anticonvulsant activity in different models. Some of the compounds demonstrated moderate to good activity in this series.Figure optionsDownload as PowerPoint slide
Journal: European Journal of Medicinal Chemistry - Volume 44, Issue 11, November 2009, Pages 4376–4384