Synthesis and .beta.-lactamase inhibitory properties of 2.beta.-[(1,2,3-triazol-1-yl)methyl]-2.alpha.-methylpenam-3.alpha.-carboxylic acid 1,1-dioxide and related triazolyl derivatives
| Autor: | Paul Spevak, Kazuo Ogawa, Samarendra N. Maiti, Ronald G. Micetich, Naobumi Ishida, Shigeru Yamabe, Akira Nakai, Motoaki Tanaka, T. W. Hall, Tomio Yamazaki |
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| Rok vydání: | 1987 |
| Předmět: |
Tazobactam
Chemical Phenomena Trimethylsilyl Stereochemistry Carboxylic acid Penicillanic Acid Sulfone Clavulanic Acids chemistry.chemical_compound Hydrogenolysis Drug Discovery Escherichia coli Beta-Lactamase Inhibitors Clavulanic Acid chemistry.chemical_classification Bacteria Bicyclic molecule Triazoles Chemistry Sulbactam chemistry Lactam Molecular Medicine Ampicillin Azide beta-Lactamase Inhibitors |
| Zdroj: | Journal of Medicinal Chemistry. 30:1469-1474 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00391a032 |
| Popis: | Benzhydryl 2 beta-[(1,2,3-triazol-1-yl)methyl]-2 alpha-methylpenam- 3 alpha-carboxylate 1,1-dioxide was prepared by heating benzhydryl 2 beta-(azidomethyl)-2 alpha-methylpenam-3 alpha-carboxylate 1,1-dioxide with (trimethylsilyl)acetylene. The ester group was removed by hydrogenolysis to give sodium 2 beta-[(1,2,3-triazol-1-yl)methyl]-2 alpha-methylpenam-3 alpha-carboxylate 1,1-dioxide (3i, YTR-830), which was found to be a potent inhibitor of various bacterial beta-lactamases. A series of related compounds was prepared in a similar way, and all of these compounds show excellent beta-lactamase inhibitory properties. |
| Databáze: | OpenAIRE |
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