Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins
| Autor: | L C, Blaszczak, R F, Brown, G K, Cook, W J, Hornback, R C, Hoying, J M, Indelicato, C L, Jordan, A S, Katner, M D, Kinnick, J H, McDonald |
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| Rok vydání: | 1990 |
| Předmět: |
Aqueous solution
Spectrophotometry Infrared medicine.drug_class Stereochemistry Hydrolysis Cephalosporin Infrared spectroscopy Microbial Sensitivity Tests Cephalosporins chemistry.chemical_compound chemistry Drug Discovery Lactam medicine Molecular Medicine Hydroxide Chemical stability Reactivity (chemistry) |
| Zdroj: | Journal of Medicinal Chemistry. 33:1656-1662 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00168a019 |
| Popis: | Nine matched pairs of cephalosporins and their 1-carba-1-dethiacephalosporin analogues have been compared with regard to microbiological activity, beta-lactam carbonyl infrared absorption, and aqueous stability. In general the microbiological activity of the pairs of compounds were very similar across a broad range of bacteria. The infrared absorption bands for the beta-lactam carbonyls of the pairs indicated a general trend for the 1-carba-1-dethiacephalosporins to absorb at lower frequencies than the corresponding cephalosporins. All of the 1-carba-1-dethiacephalosporins did however present a striking stability enhancement over their cephalosporin counterparts at pH = 10 or 11 in water. This marked contrast of MIC similarity with the observed differences in chemical reactivity clearly demonstrates hydroxide ion catalyzed hydrolysis is not a good model for transpeptidase activity unless the compounds comprise a limited domain of structural type. |
| Databáze: | OpenAIRE |
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