Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone

被引：50

作者：

Stagliano, Kenneth W.

Emadi, Ashkan

Lu, Zhenhai

Malinakova, Helena C.

Twenter, Barry

Yu, Min

Holland, Louis E.

Rom, Amanda M.

Harwood, John S.

Amin, Ronak

Johnson, Allison A.

Pommier, Yves ^{[1
]}

机构：

[1] NCI, Mol Pharmacol Lab, Canc Res Ctr, NIH, Bethesda, MD 20892 USA

[2] IIT, Dept Biol Chem & Phys Sci, Chicago, IL 60616 USA

[3] IIT, Res Inst, Chicago, IL 60616 USA

[4] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 16期

关键词：

biquinones and trimeric quinones; HIV-1 integrase inhibitor; regiocontrolled synthesis; conocurvone;

D O I：

10.1016/j.bmc.2006.04.034

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase. Published by Elsevier Ltd.

引用

页码：5651 / 5665

页数：15

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