RESUMO

Seven new 1,4-naphthoquinones structurally related to lapachol were synthesized from lawsone and oxygenated arylmercurials. These compounds can also be seen as pterocarpan derivatives where the A-ring was substituted by the 1,4-naphthoquinone nucleus. Pharmacological screening provided evidence of significant biological activities, including effects against proliferation of the MCF-7 human breast cancer cell line, against Herpes Simplex Virus type 2 infection, and against snake poison-induced myotoxicity. One derivative displaced flunitrazepam binding and showed benzodiazepine-like activity, suggesting novel neuroactive structural motifs.

Assuntos

Naftoquinonas/síntese química , Animais , Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Antivirais/síntese química , Antivirais/farmacologia , Divisão Celular/efeitos dos fármacos , Venenos de Crotalídeos/antagonistas & inibidores , Relação Dose-Resposta a Droga , Avaliação Pré-Clínica de Medicamentos , Antagonistas de Receptores de GABA-A , Herpesvirus Humano 2/efeitos dos fármacos , Humanos , Naftoquinonas/farmacologia , Neurotoxinas/antagonistas & inibidores , Ratos , Relação Estrutura-Atividade , Células Tumorais Cultivadas