Next Article in Journal
Selective C–C Coupling Reaction of Dimethylphenol to Tetramethyldiphenoquinone Using Molecular Oxygen Catalyzed by Cu Complexes Immobilized in Nanospaces of Structurally-Ordered Materials
Previous Article in Journal
New Pregnane Glycosides from Gymnema sylvestre
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(2), 3067-3088; doi:10.3390/molecules20023067

Novel Orally Active Analgesic and Anti-Inflammatory Cyclohexyl-N-Acylhydrazone Derivatives

1
Laboratório de Avaliação e Síntese de Substâncias Bioativas (LASSBio®), Instituto Nacional de Ciência e Tecnologia de Fármacos e Medicamentos (INCT-INOFAR), Universidade Federal do Rio de Janeiro, CCS, Cidade Universitária, P.O. Box 68024, Rio de Janeiro-RJ 21941-971, Brazil
2
Programa de Pós-Graduação em Química, Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro-RJ 21941-909, Brazil
3
LaFI—Laboratório de Farmacologia e Imunidade, Instituto de Ciências Biológicas e da Saúde, Universidade Federal de Alagoas, Maceió-AL 57072-900, Brazil
4
Centro de Ciências Naturais e Humanas (CCNH), Universidade Federal do ABC (UFABC) Av. dos Estados 5001, Santo André-SP 09210-580, Brazil
5
Physics Institute, UERJ, Rio de Janeiro-RJ 20550-900, Brazil
6
Programa de Pesquisa em Desenvolvimento de Fármacos, Instituto de Ciências Biomédicas, Universidade Federal do Rio de Janeiro, Rio de Janeiro-RJ 21941-902, Brazil
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 19 December 2014 / Accepted: 3 February 2015 / Published: 12 February 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [1404 KB, uploaded 12 February 2015]   |  

Abstract

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 1026 were structurally designed from molecular modification on the prototype LASSBio-294, representing a new class of cycloalkyl analogues. Compounds 1026 and their conformationally restricted analogue 9 were synthetized and evaluated as analgesic and anti-inflammatory agents in classical pharmacologic protocols. The cyclohexyl-N-acylhydrazones 1026 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. View Full-Text
Keywords: molecular simplification; N-acylhydrazone; anti-inflammatory; neuropathic pain; privileged structure; adenosine receptor molecular simplification; N-acylhydrazone; anti-inflammatory; neuropathic pain; privileged structure; adenosine receptor
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Silva, T.F.D.; Bispo Júnior, W.; Alexandre-Moreira, M.S.; Costa, F.N.; Monteiro, C.E.S.; Furlan Ferreira, F.; Barroso, R.C.R.; Noël, F.; Sudo, R.T.; Zapata-Sudo, G.; Lima, L.M.; Barreiro, E.J. Novel Orally Active Analgesic and Anti-Inflammatory Cyclohexyl-N-Acylhydrazone Derivatives. Molecules 2015, 20, 3067-3088.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top