SYNTHESIS OF C2-SYMMETRICAL AND PSEUDOSYMMETRIC HIV-1 PROTEASE INHIBITORS FROM D-MANNITOL AND D-ARABITOL

被引:41
作者
CHENERA, B
BOEHM, JC
DREYER, GB
机构
[1] Department of Medicinal Chemistry, SmithKline Beecham Pharmaceuticals, King of Prussia, PA 19406
关键词
D O I
10.1016/S0960-894X(00)80256-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Facile stereocontrolled syntheses of the potent HIV-1 protease inhibitors 1 and 2 are described, employing a unified synthetic route from carbohydrate precursors.
引用
收藏
页码:219 / 222
页数:4
相关论文
共 25 条
[11]  
KEMPF DJ, 1990, Patent No. 402646
[12]  
LEMERRER Y, 1987, HETEROCYCLES, V25, P541
[13]   HUMAN IMMUNODEFICIENCY VIRUS-1 PROTEASE EXPRESSED IN ESCHERICHIA-COLI BEHAVES AS A DIMERIC ASPARTIC PROTEASE [J].
MEEK, TD ;
DAYTON, BD ;
METCALF, BW ;
DREYER, GB ;
STRICKLER, JE ;
GORNIAK, JG ;
ROSENBERG, M ;
MOORE, ML ;
MAGAARD, VW ;
DEBOUCK, C .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (06) :1841-1845
[14]   INHIBITION OF HIV-1 PROTEASE IN INFECTED LYMPHOCYTES-T BY SYNTHETIC PEPTIDE ANALOGS [J].
MEEK, TD ;
LAMBERT, DM ;
DREYER, GB ;
CARR, TJ ;
TOMASZEK, TA ;
MOORE, ML ;
STRICKLER, JE ;
DEBOUCK, C ;
HYLAND, LJ ;
MATTHEWS, TJ ;
METCALF, BW ;
PETTEWAY, SR .
NATURE, 1990, 343 (6253) :90-92
[15]  
MEEK TD, 1990, DESIGN ANTIAIDS DRUG, V14, P225
[16]  
Meienhofer J., 1979, PEPTIDES ANAL SYNTHE, V1, P263
[17]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[18]   TOTAL SYNTHESIS OF FK506 AND AN FKBP PROBE REAGENT, (C8,C9-(C-13)2)-FK506 [J].
NAKATSUKA, M ;
RAGAN, JA ;
SAMMAKIA, T ;
SMITH, DB ;
UEHLING, DE ;
SCHREIBER, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5583-5601
[19]   3-DIMENSIONAL STRUCTURE OF ASPARTYL PROTEASE FROM HUMAN IMMUNODEFICIENCY VIRUS HIV-1 [J].
NAVIA, MA ;
FITZGERALD, PMD ;
MCKEEVER, BM ;
LEU, CT ;
HEIMBACH, JC ;
HERBER, WK ;
SIGAL, IS ;
DARKE, PL ;
SPRINGER, JP .
NATURE, 1989, 337 (6208) :615-620
[20]   HYDROXYETHYLAMINE ANALOGS OF THE P17/P24 SUBSTRATE CLEAVAGE SITE ARE TIGHT-BINDING INHIBITORS OF HIV PROTEASE [J].
RICH, DH ;
GREEN, J ;
TOTH, MV ;
MARSHALL, GR ;
KENT, SBH .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1285-1288