OPTICALLY-ACTIVE FLUORINATED BETA-LACTAM BUILDING-BLOCKS - A NOVEL FLUORINATED RETROAMIDE ISOSTERE

被引:16
作者
ABOUABDELLAH, A [1 ]
WELCH, JT [1 ]
机构
[1] SUNY ALBANY,DEPT CHEM,ALBANY,NY 12222
关键词
D O I
10.1016/0957-4166(94)80050-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new and versatile synthesis of optically active alpha-fluoro-malonamides derivatives from enantiomerically pure 3-fluoro-2-azetidinones is described. A fluorinated retroamide isostere based on these alpha-fluoro-malonamide was introduced into a small peptidomimetic for use as an HIV-1 protease inhibitor.
引用
收藏
页码:1005 / 1013
页数:9
相关论文
共 12 条
[1]  
Bodanszky M., 1984, PRACTICE PEPTIDE SYN, p143
[2]   A DOZEN YEARS OF RETRO-INVERSO PEPTIDOMIMETICS [J].
CHOREV, M ;
GOODMAN, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (05) :266-273
[3]   FLUORINATED PENICILLINS AND OTHER BETA-LACTAMS - CHEMISTRY AND BIOLOGICAL-ACTIVITY [J].
DANELON, GO ;
MASCARETTI, OA .
JOURNAL OF FLUORINE CHEMISTRY, 1992, 56 (02) :109-140
[4]   ASYMMETRIC-SYNTHESIS OF (1'R,3R,4R)-4-ACETOXY-3-(1'-((TERT-BUTYLDIMETHYLSILYL)OXY)ETHYL)-2-AZETIDINONE AND OTHER 3-(1'-HYDROXYETHYL)-2-AZETIDINONES FROM (S)-(+)-ETHYL 3-HYDROXYBUTANOATE - FORMAL TOTAL SYNTHESIS OF (+)-THIENAMYCIN [J].
GEORG, GI ;
KANT, J ;
GILL, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1129-1135
[5]   RAPID, SIMPLE, AND MILD PROCEDURE FOR ALKYLATION OF PHENOLS, ALCOHOLS, AMIDES AND ACIDS [J].
JOHNSTONE, RAW ;
ROSE, ME .
TETRAHEDRON, 1979, 35 (18) :2169-2173
[6]   VIRAL PROTEINASES - WEAKNESS IN STRENGTH [J].
KAY, J ;
DUNN, BM .
BIOCHIMICA ET BIOPHYSICA ACTA, 1990, 1048 (01) :1-18
[8]   ON SIZE OF ACTIVE SITE IN PROTEASES .I. PAPAIN [J].
SCHECHTER, I ;
BERGER, A .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1967, 27 (02) :157-+
[9]   SHORT AND UNEXPECTEDLY POTENT DIFLUOROSTATONE TYPE INHIBITORS OF HIV-1 PROTEASE [J].
SCHIRLIN, D ;
BALTZER, S ;
VANDORSSELAER, V ;
WEBER, F ;
WEILL, C ;
ALTENBURGER, JM ;
NEISES, B ;
FLYNN, G ;
REMY, JM ;
TARNUS, C .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (02) :253-258
[10]   STEREOCONTROL BY THE CARBON FLUORINE BOND AND ITS APPLICATION TO ASYMMETRIC-SYNTHESIS OF 3-FLUORO BETA-LACTAMS [J].
WELCH, JT ;
ARAKI, K ;
KAWECKI, R ;
WICHTOWSKI, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2454-2462