Synthesis, X-ray diffraction study and pharmacological evaluation of 3-amino-4-methylthiophene-2-acylcarbohydrazones

AUTOR(ES)

HERRMANN, SONJA, SCHÜBEL, TABEA, COSTA, FANNY N., BARBOSA, MARIA LETÍCIA C., FERREIRA, FABIO F., DIAS, THAYS L.M.F., ARAÚJO, MORGANA V., ALEXANDRE-MOREIRA, MAGNA S., LIMA, LÍDIA M., LAUFER, STEFAN, BARREIRO, ELIEZER J.

FONTE

An. Acad. Bras. Ciênc.

DATA DE PUBLICAÇÃO

2018

RESUMO

ABSTRACT N-acylhydrazone is an interesting privileged structure that has been used in the molecular design of a myriad of bioactive compounds. In order to identify new antinociceptive drug candidates, we described herein the design, synthesis, X-ray diffraction study and the pharmacological evaluation of a series of 3-amino-4-methylthiophene-2-acylcarbohydrazone derivatives (8a-t). Compounds were prepared in good overall yields through divergent synthesis from a common key intermediate and were characterized by classical spectroscopy methods. X-ray diffraction study was employed for unequivocal determination of the imine double bond stereochemistry. 8a-t were evaluated in vivo through oral administration using the classical writhing test in mice. N-acylhydrazone derivatives 8j and 8l displayed relative potency similar to dipyrone, highlighting them as promising analgesic lead-candidates for further investigation.

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