Síntese e avaliação da atividade antimicrobiana de furanonas halogenadas e de compostos análogos aos nostoclídeos Synthesis and evaluation of antimicrobial activity of halogenated furanones and compounds analogues to nostoclides

Abstract

Considering the broad spectrum of biological activity of gamma-butyrolactone derivatives, we presented the synthesis of 3,4-dihalo-5-arylidenefuran-2(5H)-ones (17-21) and analogues (24-28) of the natural product nostoclide (7,8). Furanones 17-21 were synthesized from the condensation of aromatic aldehydes with lactones 14 and 15, that were obtained from mucobromic and mucochloric acids. Lactone 15 was converted into the intermediate 23 in 36% overall yield. Compound 23 was then transformed into the nostoclide analogues 24-28. Some of the compounds prepared showed antimicrobial activities against Escherichia coli, Staphylococcus aureus and Bacillus cereus comparable to commercial antibiotics.

Keywords

• γ-alquilydenebutenolides
• nostoclide derivatives
• furanones