Abstract
Discovery of novel antimicrobial agents effective against infections caused by drug-resistant pathogens is an important objective. In order to find a new parenteral carbapenem antibiotic, which has potent antibacterial activity especially against methicillin-resistant staphylococci, vancomycin-resistant enterococci and penicillin-resistant Streptococcus pneumoniae, a series of 1beta-methylcarbapenems with thiazol-2-ylthio groups at the C-2 position have been synthesized. Structure-activity relationships were investigated which led to SM-197436 (27), SM-232721 (44) and SM-232724 (41), being selected for further evaluation.
MeSH terms
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Anti-Bacterial Agents* / chemical synthesis
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Anti-Bacterial Agents* / chemistry
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Anti-Bacterial Agents* / pharmacology
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Carbapenems* / chemical synthesis
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Carbapenems* / chemistry
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Carbapenems* / pharmacology
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Enterococcus / drug effects*
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Humans
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Methicillin Resistance*
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Microbial Sensitivity Tests / methods
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Penicillin Resistance
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Staphylococcus aureus / drug effects*
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Streptococcus pneumoniae / drug effects
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Structure-Activity Relationship
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Vancomycin Resistance*
Substances
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3-((4-(2,5-dihydro-1H-pyrrol-3-yl)-1,3-thiazol-2-yl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
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6-(1-hydroxyethyl)-3-((4-(2-(hydroxymethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1,3-thiazol-2-yl)thio)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
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6-(1-hydroxyethyl)-4-methyl-3-((4-(2-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1,3-thiazol-2-yl)thio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
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Anti-Bacterial Agents
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Carbapenems