Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents

Maria E S B Barros; Juliano C R Freitas; Juliana M Oliveira; Carlos H B da Cruz; Paulo B N da Silva; Larissa C C de Araújo; Gardenia C G Militão; Teresinha G da Silva; Roberta A Oliveira; Paulo H Menezes

doi:10.1016/j.ejmech.2014.02.013

Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents

Eur J Med Chem. 2014 Apr 9:76:291-300. doi: 10.1016/j.ejmech.2014.02.013. Epub 2014 Feb 11.

Affiliations

¹ Universidade Federal de Pernambuco, Departamento de Química Fundamental, Cidade Universitária, Av. Jornalista Aníbal Fernandes, s/n, Recife, PE 50740-560, Brazil.
² Universidade Federal de Pernambuco, Departamento de Fisiologia e Farmacologia, CCB, Cidade Universitária, Recife, PE, Brazil.
³ Universidade Federal de Pernambuco, Departamento de Antibióticos, Cidade Universitária, Recife, PE, Brazil.
⁴ Universidade Federal de Pernambuco, Departamento de Química Fundamental, Cidade Universitária, Av. Jornalista Aníbal Fernandes, s/n, Recife, PE 50740-560, Brazil. Electronic address: [email protected].

PMID: 24589485
DOI: 10.1016/j.ejmech.2014.02.013

Abstract

(-)-Massoialactone, an α,β-unsaturated δ-lactone isolated from Cryptocarya massoia, and five analogues were synthesized and their antiproliferative and anti-inflammatory activities were evaluated. The lactones were able to mimic the "core" functional group required for the biological activity of their parent natural compounds suggesting that substantially altered analogues may retain their properties.

Keywords: Anti-inflammatory activity; Antitumoral activity; Lactones; Massoialactone; Tellurides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Inflammatory Agents / chemical synthesis*
Anti-Inflammatory Agents / pharmacology*
Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Drug Screening Assays, Antitumor
Humans
Magnetic Resonance Spectroscopy
Mice
Mice, Inbred BALB C
Pyrones / chemical synthesis*
Pyrones / pharmacology*

Substances

6-(phenoxymethyl)-5,6-dihydro-2H-pyran-2-one
Anti-Inflammatory Agents
Antineoplastic Agents
Pyrones