SYNTHESIS AND ANTI-PSEUDOMONAL ACTIVITY OF NEW 2-ISOCEPHEMS WITH A DIHYDROXYPYRIDONE MOIETY AT C-7

被引：309

作者：

TSUJI, K

ISHIKAWA, H

机构：

[1] Microbiological Institute, Otsuka Pharmaceutical Co., Ltd., Tokushima, 771-01, Kagasuno 463-10, Kawauchi-cho

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1994年 / 4卷 / 13期

关键词：

D O I：

10.1016/S0960-894X(01)80574-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis and biological activities of optically active new 2-isocephems with a 1,3-dihydroxy-4-pyridone moiety at C-7 are described. They were found to have potent antibacterial activity against gram-negative bacteria including Pseudomonas aeruginosa. Among them, 3-[(4-methyl-5-carboxymethyl)thiazol-2-yl]thiomethyl derivative 10 d possessed excellent anti-pseudomonal in vitro potency and in vivo efficacy.

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页码：1601 / 1606

页数：6

相关论文

共 21 条

[1] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF CEPHALOSPORINS WITH C-3' CATECHOL-CONTAINING RESIDUES [J].

ARNOULD, JC ;

BERTRANDIE, A ;

BIRD, TGC ;

BOUCHEROT, D ;

JUNG, F ;

LOHMANN, JJ ;

OLIVIER, A ;

BAILEY, JP ;

BELL, W ;

DAVIES, GM .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (14) :2631-2642

[2] VINYLOGOUS VS ARYLOGOUS ISOCEPHEMS [J].

ASZODI, J ;

BONNET, A ;

CHANTOT, JF ;

COSTEROUSSE, G ;

DIDIERLAURENT, S ;

TEUTSCH, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) :2231-2236

[3]

ASZODI J, 1988, ROYAL SOC CHEM SPECI, V70, P350

[4] 5-MEMBERED HETEROCYCLIC THIONES .7. 1,2,3-THIADIAZOLE-5-THIOLATES [J].

DEMAREE, P ;

DORIA, MC ;

MUCHOWSKI, JM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (08) :1295-1298

[5] DARSTELLUNG UND EIGENSCHAFTEN DES 1.2.4- UND DES 1.3.4-THIODIAZOLS [J].

GOERDELER, J ;

OHM, J ;

TEGTMEYER, O .

CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (06) :1534-1543

[6] 7-(2-AMINOMETHYLPHENYLACETAMIDO)-3-(1-CARBOXYMETHYLTETRAZOL-5-YLTHIOMETHYL)-3-CEPHEM-4-CARBOXYLIC ACID [J].

GOTTSTEIN, WJ ;

KAPLAN, MA ;

COOPER, JA ;

SILVER, VH ;

NACHFOLGER, SJ ;

GRANATEK, AP .

JOURNAL OF ANTIBIOTICS, 1976, 29 (11) :1226-1229

[7] SYNTHESES OF NOVEL ISOPENAM AND ISOCEPHEM ANTIBIOTICS - PREPARATION OF A RETINAMIDO DERIVATIVE OF A HIGHLY STRAINED BETA-LACTAM AS POTENT ANTICANCER AGENT [J].

HAKIMELAHI, GH ;

SHIAO, MJ ;

HWU, JR ;

DAVARI, H .

HELVETICA CHIMICA ACTA, 1992, 75 (06) :1840-1847

[8]

HARO Y, 1954, PHARM B, V2, P156

[9] CEPHALOSPORINS HAVING A HETEROCYCLIC CATECHOL IN THE C3 SIDE-CHAIN .2. IMPROVEMENT OF PHARMACOKINETIC PROFILE [J].

IIMURA, S ;

IMAE, K ;

HASEGAWA, T ;

OKITA, T ;

TAMAOKA, M ;

MURATA, S ;

KAMACHI, H ;

KAMEI, H .

JOURNAL OF ANTIBIOTICS, 1993, 46 (05) :850-857

[10] CEPHALOSPORINS HAVING A HETEROCYCLIC CATECHOL IN THE C3 SIDE-CHAIN .1. ENHANCEMENT OF EFFICACY AGAINST GRAM-NEGATIVE BACTERIA [J].

IMAE, K ;

HASEGAWA, T ;

OKITA, T ;

HIRANO, M ;

KAMACHI, H ;

KAMEI, H .

JOURNAL OF ANTIBIOTICS, 1993, 46 (05) :840-849