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 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
Cite this
Synthesis and biological properties of a new series of anti-MRSA β-Lactams; 2-(thiazol-2-ylthio)carbapenems. / Shinagawa, Hisatoshi; Yamaga, Hiroshi; Houchigai, Hitoshi; Sumita, Yoshihiro; Sunagawa, Makoto.
In: Bioorganic and Medicinal Chemistry, Vol. 5, No. 3, 01.03.1997, p. 601-621.Research output: Contribution to journal › Article
}
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
PY - 1997/3/1
Y1 - 1997/3/1
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.
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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 -