Eyong Kenneth O, Kumar Ponminor S, Kuete Victor, Folefoc Gabriel N, Nkengfack Ephriam A, Baskaran Sundarababu
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India.
Bioorg Med Chem Lett. 2008 Oct 15;18(20):5387-90. doi: 10.1016/j.bmcl.2008.09.053. Epub 2008 Sep 17.
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), beta-lapachone (10) and dehydro-beta-lapachone diacetate (11) showed 100% inhibition at 25 microg/ml. All the tested samples showed dose-dependent activity.
描述了拉帕醇（1）的臭氧分解反应，该反应除了生成预期的醛6外，还意外地生成了一种强效抗肿瘤剂2-乙酰基呋喃萘醌（3）。还报道了拉帕醇（1）与CAN在干燥乙腈中反应生成具有生物活性的呋喃萘醌。采用XTT法评估了受试化合物对人DU-145前列腺癌细胞的抗肿瘤活性。结果显示，2-（1-亚乙烯基）-2,3-二氢萘并[2,3-b]呋喃-4,9-二酮（5）、β-拉帕醌（10）和脱氢-β-拉帕醌二乙酸酯（11）在25μg/ml时显示出100%的抑制率。所有受试样品均表现出剂量依赖性活性。
