SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS IN THE CEFPIROME SERIES: II. ANALOGUES OF CEFPIROME WITH DIFFERENT 7-HETEROARYLACETAMIDO AND 3'-AMMONIUM SUBSTITUENTS

The synthesis and antibacterial activity in vitro of 7-(2-heteroarylacetamido)-3-[(2, 3-cyclopentenopyridinium)methyl]cephalosporins and of some related compounds with different ammonium functions in 3'-position are described. The 7-[5-amino-1, 2, 4-thiadiazol-3-yl] and the 7-[4-aminopyrimidin-...

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Bibliographic Details
Published in:Journal of antibiotics 1988/10/25, Vol.41(10), pp.1395-1408
Main Authors: LATTRELL, RUDOLF, BLUMBACH, JÜRGEN, DUERCKHEIMER, WALTER, FLEISCHMANN, KLAUS, KIRRSTETTER, REINER, KLESEL, NORBERT, MENCKE, BURKHARD, SCHEUNEMANN, KARL-HEINZ, SCHWAB, WILFRIED, SELIGER, HUBERT, STACHE, ULRICH, WINKLER, IRWIN
Format: Article
Language:English
Subjects:
Cefpirome
Cephalosporins - chemical synthesis
Cephalosporins - pharmacology
Chemical Phenomena
Chemistry
Enterobacter - drug effects
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Klebsiella - drug effects
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Organic chemistry
Preparations and properties
Pseudomonas - drug effects
Streptococcus - drug effects
Structure-Activity Relationship
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Summary:The synthesis and antibacterial activity in vitro of 7-(2-heteroarylacetamido)-3-[(2, 3-cyclopentenopyridinium)methyl]cephalosporins and of some related compounds with different ammonium functions in 3'-position are described. The 7-[5-amino-1, 2, 4-thiadiazol-3-yl] and the 7-[4-aminopyrimidin-2-yl] analogues of cefpirome and compounds with 3-aliphatic ammoniummethyl functions have excellent antibacterial activity. Cephalosporins with different N-heterocycles other than pyridine in 3'-position are less active than their 3-pyridiniummethyl analogues. Attachment of a pyridinium group to a cephem at C-3 via a thiomethyl or an aminomethyl bridge causes reduction of antibacterial activity.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.41.1395