HIV INHIBITORY NATURAL-PRODUCTS .11. STRUCTURE, ABSOLUTE STEREOCHEMISTRY, AND SYNTHESIS OF CONOCURVONE, A POTENT, NOVEL HIV-INHIBITORY NAPHTHOQUINONE TRIMER FROM A CONOSPERMUM SP

被引：78

作者：

DECOSTERD, LA ^{[1
]}

PARSONS, IC ^{[1
]}

GUSTAFSON, KR ^{[1
]}

CARDELLINA, JH ^{[1
]}

MCMAHON, JB ^{[1
]}

CRAGG, GM ^{[1
]}

MURATA, Y ^{[1
]}

PANNELL, LK ^{[1
]}

STEINER, JR ^{[1
]}

CLARDY, J ^{[1
]}

BOYD, MR ^{[1
]}

机构：

[1] NCI,DIV CANC TREATMENT,DEV THERAPEUT PROGRAM,DRUG DISCOVERY RES & DEV LAB,BLDG 1052,ROOM 121,FREDERICK,MD 21702

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 15期

关键词：

D O I：

10.1021/ja00068a026

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bioassay-guided fractionation provided conocurvone (1), a novel trimeric naphthoquinone derivative, as the active anti-HIV constituent of an extract from a Conospermum sp. The related naphthoquinone monomer teretifolione B (2) also was isolated from a Conospermum sp. extract. The absolute stereochemistry of 2 was established by X-ray crystallographic analysis of the p-bromobenzoate derivative 6. Base-catalyzed coupling of 2 equiv of teretifolione B (2) with the deoxy derivative 8 provided compound 1, which was identical in all respects with the natural product. While compound 2 was inactive against HIV, the natural and synthetic conocurvone (1) and the synthetic trimeric analog 4 were all active and equipotent, preventing the cytopathic effects and replication of HIV in human T-lymphoblastic cells (CEM-SS) over a concentration range of 0.02-50 muM.

引用

页码：6673 / 6679

页数：7

共 14 条

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