Molecules p. 3067 - 3088 (2015)
Update date:2022-08-03
Topics:
Da Silva, Tiago Fernandes
Jnior, Walfrido Bispo
Alexandre-Moreira, Magna Suzana
Costa, Fanny Nascimento
Da Silva Monteiro, Carlos Eduardo
Ferreira, Fabio Furlan
Barroso, Regina Cely Rodrigues
Nol, Francois
Sudo, Roberto Takashi
Zapata-Sudo, Gisele
Lima, Ldia Moreira
Barreiro, Eliezer J.
The N-acylhydrazone (NAH) moiety is considered a privileged structure, being present in many compounds with diverse pharmacological activities. Among the activities attributed to NAH derivatives anti-inflammatory and analgesic ones are recurrent. As part of a research program aiming at the design of new analgesic and anti-inflammatory lead-candidates, a series of cyclohexyl-N-acylhydrazones 10-26 were structurally designed from molecular modification on the prototype LASSBio-294, representing a new class of cycloalkyl analogues. Compounds 10-26 and their conformationally restricted analogue 9 were synthetized and evaluated as analgesic and anti-inflammatory agents in classical pharmacologic protocols. The cyclohexyl-N-acylhydrazones 10-26 and the cyclohexenyl analogue 9 showed great anti-inflammatory and/or analgesic activities, but compound 13 stood out as a new prototype to treat acute and chronic painful states due to its important analgesic activity in a neuropathic pain model.
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