ENANTIOSELECTIVE SYNTHESIS AND ANTIELASTASE ACTIVITY OF 1,3,4-TRISUBSTITUTED AND 3,4-DISUBSTITUTED BETA-LACTAM ANTIBIOTICS

被引:8
作者
ADONIAS, M
ANAYA, J
CAMARA, J
CANET, E
GATEAUOLESKER, A
GERO, SD
GRANDE, M
HERNANDO, JIM
机构
[1] UNIV SALAMANCA,DEPT QUIM ORGAN,E-37008 SALAMANCA,SPAIN
[2] INST RECH INT SERVIER,F-92150 SURESNES,FRANCE
关键词
D O I
10.1016/S0960-894X(01)80714-9
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis and elastase inhibitory properties of 1,3,4-trisubstituted and 3,4-disubstituted 2-azetidinones are described. Nine of the synthesized derivatives showed elastase inhibitory activities and four of them were specific against human leukocyte elastase (HLE). 2-Deoxy-2-dithianyl-3,4;5,6-di-O-isopropylidene-D-2-glucosyl group attached to the beta-lactam nitrogen atom is related to the specificity against HLE.
引用
收藏
页码:2547 / 2552
页数:6
相关论文
共 19 条
[1]   THE USE OF RADICAL CYCLIZATION IN THE PREPARATION OF SUBSTITUTED METHYL CARBAPENEM ANTIBIOTIC PRECURSORS [J].
ANAYA, J ;
BARTON, DHR ;
GERO, SD ;
GRANDE, M ;
MARTIN, N ;
TACHDIJIAN, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (06) :867-869
[2]   ENANTIOSELECTIVE SYNTHESIS OF 2-ISOCEPHEM AND 2-OXA-ISOCEPHEM ANTIBIOTICS [J].
BARTON, DHR ;
ANAYA, J ;
GATEAUOLESKER, A ;
GERO, SD .
TETRAHEDRON LETTERS, 1992, 33 (44) :6641-6642
[3]  
BARTON DHR, 1990, J CHEM SOC P1, V11, P3211
[4]   HUMAN-LEUKOCYTE AND PORCINE PANCREATIC ELASTASE - X-RAY CRYSTAL-STRUCTURES, MECHANISM, SUBSTRATE-SPECIFICITY, AND MECHANISM-BASED INHIBITORS [J].
BODE, W ;
MEYER, E ;
POWERS, JC .
BIOCHEMISTRY, 1989, 28 (05) :1951-1963
[5]  
DOHERTY JB, 1986, NATURE, V322, P192, DOI 10.1038/322192a0
[6]   INHIBITION OF HUMAN-LEUKOCYTE ELASTASE .4. SELECTION OF A SUBSTITUTED CEPHALOSPORIN (L-658,758) AS A TOPICAL AEROSOL [J].
FINKE, PE ;
SHAH, SK ;
ASHE, BM ;
BALL, RG ;
BLACKLOCK, TJ ;
BONNEY, RJ ;
BRAUSE, KA ;
CHANDLER, GO ;
COTTON, M ;
DAVIES, P ;
DELLEA, PS ;
DORN, CP ;
FLETCHER, DS ;
OGRADY, LA ;
HAGMANN, WK ;
HAND, KM ;
KNIGHT, WB ;
MAYCOCK, AL ;
MUMFORD, RA ;
OSINGA, DG ;
SOHAR, P ;
THOMPSON, KR ;
WESTON, H ;
DOHERTY, JB .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (21) :3731-3744
[7]  
FIRESTONE RA, 1990, TETRAHEDRON, V46, P2255
[8]   PREVENTION OF HUMAN-LEUKOCYTE ELASTASE-MEDIATED LUNG DAMAGE BY 3-ALKYL-4-AZETIDINONES [J].
HAGMANN, WK ;
SHAH, SK ;
DORN, CP ;
OGRADY, LA ;
HALE, JJ ;
FINKE, PE ;
THOMPSON, KR ;
BRAUSE, KA ;
ASHE, BM ;
WESTON, H ;
DAHLGREN, ME ;
MAYCOCK, AL ;
DELLEA, PS ;
HAND, KM ;
OSINGA, DG ;
BONNEY, RJ ;
DAVIES, P ;
FLETCHER, DS ;
DOHERTY, JB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (10) :545-550
[9]   THE EFFECT OF N-ACYL SUBSTITUENTS ON THE STABILITY OF MONOCYCLIC BETA-LACTAM INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE [J].
HAGMANN, WK ;
THOMPSON, KR ;
SHAH, SK ;
FINKE, PE ;
ASHE, BM ;
WESTON, H ;
MAYCOCK, AL ;
DOHERTY, JB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (07) :681-684
[10]  
MAILLARD JL, 1990, EUR J CELL BIOL, P213