Abstract
A series of 1β-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1β-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I.
| Original language | English |
|---|---|
| Pages (from-to) | 601-621 |
| Number of pages | 21 |
| Journal | Bioorganic and Medicinal Chemistry |
| Volume | 5 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - Mar 1 1997 |
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
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Shinagawa, H., Yamaga, H., Houchigai, H., Sumita, Y., & Sunagawa, M. (1997). Synthesis and biological properties of a new series of anti-MRSA β-Lactams; 2-(thiazol-2-ylthio)carbapenems. Bioorganic and Medicinal Chemistry, 5(3), 601-621. https://doi.org/10.1016/S0968-0896(96)00273-8