CEPHALOSPORINS HAVING A HETEROCYCLIC CATECHOL IN THE C3 SIDE CHAIN I. ENHANCEMENT OF EFFICACY AGAINST GRAM-NEGATIVE BACTERIA

Two groups of cephalosporins substituted with a variety of heterocyclic catechols in the C3 side chain were synthesized. One is a group of 3-(heterocyclic catechol-substituted methyl)cephalosporins and another is 3-[(E)-3-heterocyclic catechol-substituted l-propen-l-yl]cephalosporins. Cephalosporins...

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Published inJournal of antibiotics Vol. 46; no. 5; pp. 840 - 849
Main Authors KAMACHI, HAJIME, HASEGAWA, TOSHIFUMI, KAMEI, HIDEO, IMAE, KIYOTO, OKITA, TAKAAKI, HIRANO, MINORU, IIMURA, SEIJI
Format Journal Article
LanguageEnglish
Published Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1993
Japan Antibiotics Research Association
Subjects
Animals
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Ceftazidime - pharmacology
Cephalosporins - chemical synthesis
Cephalosporins - pharmacokinetics
Cephalosporins - pharmacology
Half-Life
Imipenem - pharmacology
Medical sciences
Mice
Microbial Sensitivity Tests
Pharmacology. Drug treatments
Pseudomonas Infections - drug therapy
Stereoisomerism
Structure-Activity Relationship
Microorganism growth
Molecular structure
Rodentia
Lactam
In vitro
Chemical substitution
Infection
In vivo
Vertebrata
Chemotherapy
Cephalosporin derivatives
Mammalia
Sensitivity resistance
Synthesis
Treatment
Structure activity relation
Mouse
Animal
Bacteriosis
Bacteria
Comparative study
Heterocyclic compound
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Summary:Two groups of cephalosporins substituted with a variety of heterocyclic catechols in the C3 side chain were synthesized. One is a group of 3-(heterocyclic catechol-substituted methyl)cephalosporins and another is 3-[(E)-3-heterocyclic catechol-substituted l-propen-l-yl]cephalosporins. Cephalosporins in the latter group showed higher in vivo efficacies than those in the former group having the same heterocyclic catechol, especially against Pseudomonas aeruginosa A9843A, although there was no significant difference between their in vitro activity. Among the latter group, the 5, 6-dihydroxybenzimidazole derivative (6e) and the 2, 6-dihydro-7-hydroxy-6-oxo-isoquinoline derivative (6b) showed much higher activity than ceftazidime (CAZ) and imipenem (IPM) against P. aeruginosa A9843A both in in vitro and in vivo studies.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.46.840