Synthesis and preliminary pharmacological evaluation of new (±) 1,4-naphthoquinones structurally related to lapachol

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 activitics, 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 berizodiazepine-like activity, Suggesting novel neuroactive structural motifs. (C) 2002 Elsevier Science Ltd. All rights reserved.