Solid-phase synthesis of the alkenyldiarylmethane (ADAM) series of non-nucleoside HIV-1 reverse transcriptase inhibitors

被引：25

作者：

Xu, GZ

Loftus, TL

Wargo, H

Turpin, JA

Buckheit, RW

Cushman, M ^{[1
]}

机构：

[1] Purdue Univ, Sch Pharm & Pharmacal Sci, Dept Med Chem & Mol Pharmacol, W Lafayette, IN 47907 USA

[2] So Res Inst, Infect Dis Res Dept, Frederick, MD 21701 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 18期

关键词：

D O I：

10.1021/jo0100291

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Sonogashira and Stille cross-coupling reactions have been employed in the synthesis of several non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the alkenyldiarylmethane (ADAM) series. The synthesis has been carried out both in solution and on a solid support. In contrast to previous syntheses of NNRTIs in the ADAM series, the present strategy allows the incorporation of differently substituted aromatic rings in a stereochemically defined fashion. The most potent of the new ADAMs inhibited the cytopathic effect of HIV-1(RF) in CEM-SS cell culture with an EC50 value of 20 nM.

引用

页码：5958 / 5964

页数：7

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