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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1991年 / 1卷 / 04期

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

页码：219 / 222

页数：4

共 25 条

[1] AN INHIBITOR OF THE PROTEASE BLOCKS MATURATION OF HUMAN AND SIMIAN IMMUNODEFICIENCY VIRUSES AND SPREAD OF INFECTION [J].

ASHORN, P ;

MCQUADE, TJ ;

THAISRIVONGS, S ;

TOMASSELLI, AG ;

TARPLEY, WG ;

MOSS, B .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (19) :7472-7476

[2]

DARKE PL, 1989, J BIOL CHEM, V264, P2307

[3] INHIBITION OF HUMAN IMMUNODEFICIENCY VIRUS-1 PROTEASE INVITRO - RATIONAL DESIGN OF SUBSTRATE-ANALOG INHIBITORS [J].

DREYER, GB ;

METCALF, BW ;

TOMASZEK, TA ;

CARR, TJ ;

CHANDLER, AC ;

HYLAND, L ;

FAKHOURY, SA ;

MAGAARD, VW ;

MOORE, ML ;

STRICKLER, JE ;

DEBOUCK, C ;

MEEK, TD .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (24) :9752-9756

[4] DIASTEREOSPECIFIC SYNTHESIS OF DIAZIRIDINES FROM D-MANNITOL - ACCESS TO CHIRAL ALPHA-AMINO-ACIDS [J].

DUREAULT, A ;

GRECK, C ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1986, 27 (35) :4157-4160

[5] NUCLEOPHILIC OPENING OF CHIRAL BIS-AZIRIDINES - A ROUTE TO ENANTIOMERICALLY PURE ALPHA-AMINO-ACIDS AND POLYSUBSTITUTED PIPERIDINES [J].

DUREAULT, A ;

TRANCHEPAIN, I ;

GRECK, C ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1987, 28 (29) :3341-3344

[6] NUCLEOPHILIC OPENING OF CHIRAL BIS(AZIRIDINES) - A ROUTE TO ENANTIOMERICALLY PURE ALPHA-AMINO ALDEHYDES OR ACIDS AND POLYSUBSTITUTED PIPERIDINES [J].

DUREAULT, A ;

TRANCHEPAIN, I ;

DEPEZAY, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5324-5330

[7] DESIGN, ACTIVITY, AND 2.8 A CRYSTAL-STRUCTURE OF A C2 SYMMETRICAL INHIBITOR COMPLEXED TO HIV-1 PROTEASE [J].

ERICKSON, J ;

NEIDHART, DJ ;

VANDRIE, J ;

KEMPF, DJ ;

WANG, XC ;

NORBECK, DW ;

PLATTNER, JJ ;

RITTENHOUSE, JW ;

TURON, M ;

WIDEBURG, N ;

KOHLBRENNER, WE ;

SIMMER, R ;

HELFRICH, R ;

PAUL, DA ;

KNIGGE, M .

SCIENCE, 1990, 249 (4968) :527-533

[8] RENIN INHIBITORS [J].

GREENLEE, WJ .

MEDICINAL RESEARCH REVIEWS, 1990, 10 (02) :173-236

[9] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES [J].

HENRY, JR ;

MARCIN, LR ;

MCINTOSH, MC ;

SCOLA, PM ;

HARRIS, GD ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1989, 30 (42) :5709-5712

[10] STRUCTURE-BASED, C2 SYMMETRICAL INHIBITORS OF HIV PROTEASE [J].

KEMPF, DJ ;

NORBECK, DW ;

CODACOVI, LM ;

WANG, XC ;

KOHLBRENNER, WE ;

WIDEBURG, NE ;

PAUL, DA ;

KNIGGE, MF ;

VASAVANONDA, S ;

CRAIGKENNARD, A ;

SALDIVAR, A ;

ROSENBROOK, W ;

CLEMENT, JJ ;

PLATTNER, JJ ;

ERICKSON, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2687-2689

← 1 2 3 →