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Molecules 2014, 19(6), 8456-8471; https://doi.org/10.3390/molecules19068456

3-Aminothiophene-2-Acylhydrazones: Non-Toxic, Analgesic and Anti-Inflammatory Lead-Candidates

1
LaFI—Laboratório de Farmacologia e Imunidade, Instituto de Ciências Biológicas e da Saúde, Universidade Federal de Alagoas, Maceió 57072-900, AL, Brazil
2
Laboratório de Avaliação e Síntese de Substâncias Bioativas—LASSBio, Programa de Pesquisa em Desenvolvimento de Fármacos, Instituto de Ciências Biomédicas, Universidade Federal do Rio de Janeiro, PO Box 68024, Rio de Janeiro 21944-902, RJ, Brazil
3
Centro de Biotecnologia Genomica, Instituto Politecnico Nacional, Boulevard del Maestro, s/n, 88710 Reynosa, Mexico
*
Author to whom correspondence should be addressed.
Received: 19 May 2014 / Revised: 5 June 2014 / Accepted: 6 June 2014 / Published: 20 June 2014
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [693 KB, uploaded 20 June 2014]   |  

Abstract

Different chemotypes are described as anti-inflammatory. Among them the N-acylhydrazones (NAH) are highlighted by their privileged structure nature, being present in several anti-inflammatory drug-candidates. In this paper a series of functionalized 3-aminothiophene-2-acylhydrazone derivatives 5ai were designed, synthesized and bioassayed. These new derivatives showed great anti-inflammatory and analgesic potency and efficacy. Compounds 5a and 5d stand out in this respect, and were also active in CFA-induced arthritis in rats. After daily treatment for seven days with 5a and 5d (50 µmol/Kg), by oral administration, these compounds were not renal or hepatotoxic nor immunosuppressive. Compounds 5a and 5d also displayed good drug-scores and low risk toxicity calculated in silico using the program OSIRIS Property Explorer. View Full-Text
Keywords: anti-inflammatory; toxicity; acylhydrazone; analgesic; arthritis; privileged structure anti-inflammatory; toxicity; acylhydrazone; analgesic; arthritis; privileged structure
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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MDPI and ACS Style

Silva, Y.K.C.; Reyes, C.T.M.; Rivera, G.; Alves, M.A.; Barreiro, E.J.; Moreira, M.S.A.; Lima, L.M. 3-Aminothiophene-2-Acylhydrazones: Non-Toxic, Analgesic and Anti-Inflammatory Lead-Candidates. Molecules 2014, 19, 8456-8471.

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