TY - JOUR
T1 - Synthesis and biological properties of a new series of anti-MRSA β-Lactams; 2-(thiazol-2-ylthio)carbapenems
AU - Shinagawa, Hisatoshi
AU - Yamaga, Hiroshi
AU - Houchigai, Hitoshi
AU - Sumita, Yoshihiro
AU - Sunagawa, Makoto
N1 - Copyright:
Copyright 2007 Elsevier B.V., All rights reserved.
PY - 1997/3
Y1 - 1997/3
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0031105521&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031105521&partnerID=8YFLogxK
U2 - 10.1016/S0968-0896(96)00273-8
DO - 10.1016/S0968-0896(96)00273-8
M3 - Article
C2 - 9113338
AN - SCOPUS:0031105521
VL - 5
SP - 601
EP - 621
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 3
ER -