1. Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.
- Author
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Bonifazi EL, Ríos-Luci C, León LG, Burton G, Padrón JM, and Misico RI
- Subjects
- Cell Line, Tumor, Drug Screening Assays, Antitumor, Humans, Indicators and Reagents, Lipids chemistry, Magnetic Resonance Spectroscopy, Prenylation, Structure-Activity Relationship, Antineoplastic Agents, Phytogenic chemical synthesis, Antineoplastic Agents, Phytogenic pharmacology, Naphthoquinones chemical synthesis, Naphthoquinones chemistry, Naphthoquinones pharmacology
- Abstract
A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI(50) values of 0.42-8.1 and 0.80-2.2microM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity., (Copyright 2010 Elsevier Ltd. All rights reserved.)
- Published
- 2010
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