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Bioorg Med Chem Lett ; 24(18): 4381-4383, 2014 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-25176328

RESUMO

Research on dolabellane diterpenes of brown algae Dictyota spp. has shown that these diterpenoids have strong anti-HIV-1 activity, but there are not data about antiviral activity of dolabellane diterpenes isolated from octocorals, which are antipodes of those isolated from the brown algae. Dolabellanes 13-keto-1(R),11(S)-dolabella-3(E),7(E),12(18)-triene (1) and ß-Araneosene (2) were isolated from the Caribbean octocoral Eunicea laciniata, and both showed low anti-HIV-1 activity and low toxicity. Since it was shown that oxygenated dolabellanes from algae have better anti-HIV-1 activity, in this work some derivatives of the main dolabellane of E. laciniata1 were obtained by epoxidation (3), epoxide opening (4), and allylic oxidation (5). The derivatives showed significant improvement in the anti-HIV-1potency (100-fold), being compounds 3 and 5 the most active ones. Their high antiviral activities, along with their low cytotoxicity, make them promissory antiviral compounds; and it is worth noting that the absolute configuration at the ring junction in the dolabellane skeleton does not seem to be determinant in the antiviral potency of these diterpeneoids.


Assuntos
Fármacos Anti-HIV/farmacologia , Diterpenos/química , HIV/efeitos dos fármacos , Oxigênio/química , Fármacos Anti-HIV/síntese química , Fármacos Anti-HIV/química , Linhagem Celular Transformada , Relação Dose-Resposta a Droga , Humanos , Testes de Sensibilidade Microbiana , Conformação Molecular , Relação Estrutura-Atividade
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