Synthesis of enantiomerically pure cis and trans 2-aminocyclopentanecarboxylic acids. Use of proline replacements in potential HIV-protease inhibitors.

被引:25
作者
Noteberg, D
Branalt, J
Kvarnstrom, I
Classon, B
Samuelsson, B
Nillroth, U
Danielson, H
Karlen, A
Hallberg, A
机构
[1] UNIV STOCKHOLM,ARRHENIUS LAB,DEPT ORGAN CHEM,S-10691 STOCKHOLM,SWEDEN
[2] LINKOPING UNIV,DEPT CHEM,S-58183 LINKOPING,SWEDEN
[3] UNIV UPPSALA,DEPT BIOCHEM,S-75123 UPPSALA,SWEDEN
[4] UNIV UPPSALA,DEPT ORGAN PHARMACEUT CHEM,S-75123 UPPSALA,SWEDEN
[5] AB HASSLE,S-43183 MOLNDAL,SWEDEN
关键词
D O I
10.1016/S0040-4020(97)00482-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the four diastereomeric 2-aminocyclopentanecarboxylic acids, their use as replacements for proline in potential HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere and the evaluation of the biological activity of these is described. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7975 / 7984
页数:10
相关论文
共 32 条
[1]  
BARTOLI G, 1994, J ORG CHEM, V59, P5228
[2]  
BRANALT J, UNPUB
[3]   METAL-SALTS AS NEW CATALYSTS FOR MILD AND EFFICIENT AMINOLYSIS OF OXIRANES [J].
CHINI, M ;
CROTTI, P ;
MACCHIA, F .
TETRAHEDRON LETTERS, 1990, 31 (32) :4661-4664
[4]   NOVEL HIV-1 PROTEASE INHIBITORS CONTAINING A BETA-HYDROXY SULFIDE ISOSTERE [J].
CHO, SYS ;
JUNGHEIM, LN ;
BAXTER, AJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (05) :715-720
[5]   Biocatalysis for the preparation of optically active beta-lactam precursors of amino acids [J].
Csomos, P ;
Kanerva, LT ;
Bernath, G ;
Fulop, F .
TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1789-1796
[6]   ASYMMETRIC-SYNTHESIS OF (-)-(1R,2S)-CISPENTACIN AND RELATED CIS-2-AMINO AND TRANS-2-AMINO CYCLOPENTANE-1-CARBOXYLIC AND CYCLOHEXANE-1-CARBOXYLIC ACIDS [J].
DAVIES, SG ;
ICHIHARA, O ;
LENOIR, I ;
WALTERS, IAS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11) :1411-1415
[7]   WHOLE CELL CATALYZED KINETIC RESOLUTION OF 6-AZABICYCLO[3.2.0]HEPT-3-EN-7-ONE - SYNTHESIS OF (-)-CISPENTACIN (FR 109615) [J].
EVANS, C ;
MCCAGUE, R ;
ROBERTS, SM ;
SUTHERLAND, AG ;
WISDOM, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2276-2277
[8]   THE DEVELOPMENT OF CYCLIC SULFOLANES AS NOVEL AND HIGH-AFFINITY P(2) LIGANDS FOR HIV-1 PROTEASE INHIBITORS [J].
GHOSH, AK ;
LEE, HY ;
THOMPSON, WJ ;
CULBERSON, C ;
HOLLOWAY, MK ;
MCKEE, SP ;
MUNSON, PM ;
DUONG, TT ;
SMITH, AM ;
DARKE, PL ;
ZUGAY, JA ;
EMINI, EA ;
SCHLEIF, WA ;
HUFF, JR ;
ANDERSON, PS .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (08) :1177-1188
[9]   POTENT HIV PROTEASE INHIBITORS - THE DEVELOPMENT OF TETRAHYDROFURANYLGLYCINES AS NOVEL P(2)-LIGANDS AND PYRAZINE AMIDES AS P(3)-LIGANDS [J].
GHOSH, AK ;
THOMPSON, WJ ;
HOLLOWAY, MK ;
MCKEE, SP ;
DUONG, TT ;
LEE, HY ;
MUNSON, PM ;
SMITH, AM ;
WAI, JM ;
DARKE, PL ;
ZUGAY, JA ;
EMINI, EA ;
SCHLEIF, WA ;
HUFF, JR ;
ANDERSON, PS .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (16) :2300-2310
[10]  
Girijavallabhan V M, 1994, Bioorg Med Chem, V2, P1075, DOI 10.1016/S0968-0896(00)82057-X