Synthesis and biological properties of new 1beta-methylcarbapenems containing heteroaromatic thioether moiety.
The synthesis and biological activities of a series of new 1beta-methylcarbapenems 1a-h having heteroaromatic thioether moiety at C-5 position of pyrrolidine were described. Among these compounds, 1,2,3-thiadiazole derivative 1h showed the most potent antibacterial activity and advanced pharmacokinetics in comparison with meropenem.
Shin
K J
KJ
Medicinal Chemistry Research Center, Korea Institute of Science and Technology, Seoul 130-650, South Korea.
Koo
K D
KD
Yoo
K H
KH
Kang
Y K
YK
Park
S W
SW
Kim
D J
DJ
D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D019540:Area Under Curve; D015780:Carbapenems / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D004353:Drug Evaluation, Preclinical / Q000379:methods; D000077731:Meropenem; D008826:Microbial Sensitivity Tests; D051381:Rats; D013845:Thienamycins / Q000737:chemistry / Q000494:pharmacology
C442398:1-aza-6-(1-hydroxyethyl)-4-methyl-7-oxo-3-(((2-(1,2,3-thiadiazol-5-yl)thiomethyl)pyrrolidin-4-yl)thio)bicyclo(3.2.0)heptane-2-carboxylic acid; D000890:Anti-Infective Agents; D015780:Carbapenems; D013845:Thienamycins; D000077731:Meropenem