Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents. 1. Conversion of 5-substituent on oxazolidinone

被引：31
|
作者：
Tokuyama, R [1 ]
Takahashi, Y [1 ]
Tomita, Y [1 ]
Suzuki, T [1 ]
Yoshida, T [1 ]
Iwasaki, N [1 ]
Kado, N [1 ]
Okezaki, E [1 ]
Nagata, O [1 ]
机构：
[1] Hokuriku Seiyaku Co Ltd, Div Res & Dev, Katsuyama, Fukui 9118555, Japan
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 2001年 / 49卷 / 04期
关键词：
oxazolidinone; antibacterial activity; 5-substituted oxazolidinone; structure-activity relationship;
D O I：
10.1248/cpb.49.347
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A structure-activity relationship (SAR) study on 5-substituted oxazolidinones as an antibacterial agent is described. The oxazolidinones, of which 5-acetylaminomethyl moiety was converted into other functions, were prepared and evaluated for antibacterial activity. Elongation of the methylene chain (8) and conversion of the acetamido moiety into guanidino moiety (12) decreased the antibacterial activity. The replacement of carbonyl oxygen (=O) by thiocarbonyl sulfur (=S) enhanced in vitro antibacterial activity. Especially, compound 16, which had the 5-thiourea group, showed 4-8 stronger in vitro activity than linezolid. Our SAR study revealed that the antibacterial activity was greatly affected by the conversion of 5-substituent.
引用
收藏
页码：347 / 352
页数：6
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