Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol

Eyong, Kenneth O. ; Kumar, Ponminor S. ; Kuete, Victor ; Folefoc, Gabriel N. ; Nkengfack, Ephriam A. ; Baskaran, Sundarababu (2008) Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol Bioorganic & Medicinal Chemistry Letters, 18 (20). pp. 5387-5390. ISSN 0960-894X

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.bmcl.2008.09.053

Abstract

Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (5), β-lapachone (10) and dehydro-β-lapachone diacetate (11) showed 100% inhibition at 25 μg/ml. All the tested samples showed dose-dependent activity.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Anticancer; Lapachol; Furanonaphthoquinones; Ozonolysis; CAN; Radical Cyclization
ID Code:98544
Deposited On:18 Sep 2014 11:32
Last Modified:18 Sep 2014 11:32

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