SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF C4 SUBSTITUTED MONOBACTAMS

被引：17

作者：

ARNOULD, JC

BOUTRON, P

PASQUET, MJ

机构：

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 1992年 / 27卷 / 02期

关键词：

MONOBACTAM; CATECHOL; ANTIBACTERIAL ACTIVITY; AZETIDINONE; BETA-LACTAM;

D O I：

10.1016/0223-5234(92)90101-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis and antibacterial activity of a series of monobactams having various substituents at C4 position is described. An efficient route to versatile intermediates 4a-c from 6-aminopenicillanic acid (6-APA) has been developed. Derivatives 10e, 11, 21 showed good to moderate activity against Gram-negative bacteria with the exception of Pseudomonas aeruginosa. Introduction of a catechol moiety on the C4 side chain only slightly improved the activity against P aeruginosa.

引用

收藏

页码：131 / 140

页数：10

相关论文

共 29 条

[1] KETENE ALKYLTRIALKYLSILYL ACETALS - SYNTHESIS, PRYOLYSIS AND NMR STUDIES [J].

AINSWORTH, C ;

CHEN, F ;

KUO, YN .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 46 (01) :59-+

[2]

ATTRIL R, 1984, J ORG CHEM, V249, P1679

[3]

AUGSTEIN J, 1974, Patent No. 1345075

[4] ACYLATION OF DIBASIC COMPOUNDS CONTAINING AMINO AMIDINE AND AMINOGUANIDINE FUNCTIONS [J].

BARKER, PL ;

GENDLER, PL ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) :2455-2465

[5]

BREUER H, 1985, I5TH INT C ANT AG CH, P371

[6] 4-ALKYLATED MONOBACTAMS - CHIRAL SYNTHESIS AND ANTI-BACTERIAL ACTIVITY [J].

CIMARUSTI, CM ;

BONNER, DP ;

BREUER, H ;

CHANG, HW ;

FRITZ, AW ;

FLOYD, DM ;

KISSICK, TP ;

KOSTER, WH ;

KRONENTHAL, D ;

MASSA, F ;

MUELLER, RH ;

PLUSCEC, J ;

SLUSARCHYK, WA ;

SYKES, RB ;

TAYLOR, M ;

WEAVER, ER .

TETRAHEDRON, 1983, 39 (15) :2577-2589

[7] IRON-REGULATED OUTER-MEMBRANE PROTEINS OF ESCHERICHIA-COLI-K-12 AND MECHANISM OF ACTION OF CATECHOL-SUBSTITUTED CEPHALOSPORINS [J].

CURTIS, NAC ;

EISENSTADT, RL ;

EAST, SJ ;

CORNFORD, RJ ;

WALKER, LA ;

WHITE, AJ .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1988, 32 (12) :1879-1886

[8]

HANNAH J, 1982, J MED CHEM, P457

[9] SULFAZECIN AND ISOSULFAZECIN, NOVEL BETA-LACTAM ANTIBIOTICS OF BACTERIAL ORIGIN [J].

IMADA, A ;

KITANO, K ;

KINTAKA, K ;

MUROI, M ;

ASAI, M .

NATURE, 1981, 289 (5798) :590-591

[10] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF C-4-AMINO ACID SUBSTITUTED MONOBACTAM ANALOGS [J].

KIM, KS ;

CHAMBERS, JH .

JOURNAL OF ANTIBIOTICS, 1987, 40 (01) :124-129