STUDIES ON ORALLY ACTIVE CEPHALOSPORINS: I. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF NEW 3-SUBSTITUTED CARBAMOYLOXYMETHYL CEPHALOSPORINS

The synthesis and antibacterial activities of 7β-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetarnido]-3-N, N-dimethylcarbamoyloxymethyl-3-cephem-4-carboxylic acid (E1 100) and its analogs are described, as well as oral absorbability and in vivo activities of the l-(isopropoxycarbonyloxy)ethyl ester (E...

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Bibliographic Details
Published in:Journal of antibiotics 1994/12/25, Vol.47(12), pp.1507-1525
Main Authors: NEGI, SHIGETO, YAMANAKA, MOTOSUKE, SUGIYAMA, ISAO, KOMATSU, YUKI, SASHO, MANABU, TSURUOKA, AKIHIKO, KAMADA, ATSUSHI, TSUKADA, ITARU, HIRUMA, RYOICHI, KATSU, KANEMASA, MACHIDA, YOSHIMASA
Format: Article
Language:English
Subjects:
Administration, Oral
Animals
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Biological Availability
Cephalosporins - administration & dosage
Cephalosporins - chemistry
Cephalosporins - pharmacology
Haemophilus influenzae
Male
Medical sciences
Mice
Mice, Inbred ICR
Microbial Sensitivity Tests
Pharmacology. Drug treatments
Structure-Activity Relationship
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Summary:The synthesis and antibacterial activities of 7β-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetarnido]-3-N, N-dimethylcarbamoyloxymethyl-3-cephem-4-carboxylic acid (E1 100) and its analogs are described, as well as oral absorbability and in vivo activities of the l-(isopropoxycarbonyloxy)ethyl ester (E1 101) and its analogous esters. The introduction of acyclic and cyclic lower alkyl groups at the N-position of 3-carbamoyloxymethyl cephems influences antibacterial activities, especially against H. influenzae, and oral absorbability of their prodrug esters. The structure-activity relationships are also discussed.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.47.1507