SYNTHESIS OF GAMMA-LACTAM ANALOGS OF 1-ACETOXY CARBAPENEM DERIVATIVES

被引:11
作者
COULTON, S
FRANCOIS, I
SOUTHGATE, R
机构
[1] SmithKline Beecham Pharmaceuticals, Research Division, Betchworth, Surrey RH3 7AJ, Brockham Park
关键词
D O I
10.1016/S0040-4039(00)97208-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of γ-lactam analogues of the 1-acetoxy carbapenem esters, from dl-pyroglutamic acid are described. Attempted deprotection to provide the free carboxylic acids resulted in degradation. Whilst the free acid of the 1-hydroxy carbapenem analogue was chemically stable, it lacked antibacterial activity. © 1990.
引用
收藏
页码:6923 / 6926
页数:4
相关论文
共 7 条
[1]   A GAMMA-LACTAM ANALOG OF THE PENEMS POSSESSING ANTIBACTERIAL ACTIVITY [J].
BALDWIN, JE ;
FREEMAN, RT ;
LOWE, C ;
SCHOFIELD, CJ ;
LEE, E .
TETRAHEDRON, 1989, 45 (14) :4537-4550
[2]   SYNTHESIS OF SOME 4-ACYLOXY-7-OXO-1-AZABICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLATES [J].
BATESON, JH ;
QUINN, AM ;
SOUTHGATE, R .
TETRAHEDRON LETTERS, 1987, 28 (14) :1561-1564
[3]  
HASIGUCHI S, 1988, J CHEM SOC P1, P2345
[4]   ELECTROCHEMICAL SYNTHESIS OF SEMICYCLIC AND CYCLIC N-ACYL N,O-ACETALS [J].
IWASAKI, T ;
HORIKAWA, H ;
MATSUMOTO, K ;
MIYOSHI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) :1552-1554
[5]   1-ACETOXYCARBAPENEMS [J].
KOLLER, W ;
LINKIES, A ;
PIETSCH, H ;
REHLING, H ;
REUSCHLING, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (07) :537-537
[6]   MILD DEPROTECTION OF CARBAPENEM ESTERS WITH ALUMINUM TRICHLORIDE [J].
OHTANI, M ;
WATANABE, F ;
NARISADA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5271-5272
[7]   CEPHALOSPORINS TO CARBAPENEMS - 1-OXYGENATED CARBAPENEMS AND CARBAPENAMS [J].
ROSATI, RL ;
KAPILI, LV ;
MORRISSEY, P ;
RETSEMA, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :291-297