Synthesis and antibacterial evaluation of 1β-methyl-2-[5-(1-methoxyimino-2-substituted sulfonamide ethyl)pyrrolidin-3-ylthio]carbapenems and their related compounds

被引：13
作者：
Jeon, Heechol
Jo, Nam Hyun
Yoo, Kyung Ho
Choi, Joung-Hoon
Cho, Heeyeong
Cho, Jung-Hyuck
Oh, Chang-Hyun
机构：
[1] Korea Inst Sci & Technol, Med Chem Res Ctr, Seoul 130650, South Korea
[2] Hanyang Univ, Dept Chem, Seoul 133791, South Korea
[3] Korea Res Inst Chem Technol, Pharmaceut Screening Lab, Taejon 305600, South Korea
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2007年 / 42卷 / 03期
关键词：
1; beta-methylcarbapenems; antibacterial activity; DHP-I stability;
D O I：
10.1016/j.ejmech.2006.10.006
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The synthesis of a new series of 1 beta-methylcarbapenems having methoxyimine and substituted sulfonamide moieties is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the pyrrolidine ring was investigated. A particular compound (IIIc) having methylaminosulfonamide moiety showed the most potent antibacterial activity. (c) 2006 Elsevier Masson SAS. All rights reserved.
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收藏
页码：358 / 364
页数：7
相关论文
共 14 条
[1]  
BIRNBAUM J, 1985, AM J MED, V78, P3, DOI 10.1016/0002-9343(85)90097-X
[2]   In vivo activity and pharmacokinetic evaluation of a novel long-acting carbapenem antibiotic, MK-826 (L-749,345) [J].
Gill, CJ ;
Jackson, JJ ;
Gerckens, LS ;
Pelak, BA ;
Thompson, RK ;
Sundelof, JG ;
Kropp, H ;
Rosen, H .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1998, 42 (08) :1996-2001
[3]  
INOUE K, 1994, 34 INT C ANT AG CHEM
[4]   A novel 1 beta-methylcarbapenem antibiotic, S-4661 synthesis and structure-activity relationships of 2-(5-substituted pyrrolidin-3-ylthio)-1 beta-methylcarbapenems [J].
Iso, Y ;
Irie, T ;
Nishino, Y ;
Motokawa, K ;
Nishitani, Y .
JOURNAL OF ANTIBIOTICS, 1996, 49 (02) :199-209
[5]   Low convulsive activity of a new carbapenem antibiotic, DK-35C, as compared with existing congeners [J].
Jin, C ;
Jung, I ;
Ku, HJ ;
Yook, J ;
Kim, DH ;
Kim, M ;
Cho, JH ;
Oh, CH .
TOXICOLOGY, 1999, 138 (02) :59-67
[6]  
LEANZA WJ, 1979, J MED CHEM, V22, P1435, DOI 10.1021/jm00198a001
[7]   Synthesis and biological evaluation of 1β-methylcarbapenems having guanidino moieties [J].
Oh, CH ;
Cho, JH .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (01) :50-55
[8]   Synthesis and antibacterial activity of 1β-methyl-2-[5-(N-substituted-2-hydroxy iminoethyl)pyrrolidin-3-ylthio]carbapenem derivatives [J].
Oh, CH ;
Lee, SC ;
Cho, JH .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (7-8) :751-758
[9]   STUDIES ON THE SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW ZWITTERIONIC CARBAPENEMS [J].
OH, CH ;
CHO, JH .
JOURNAL OF ANTIBIOTICS, 1994, 47 (01) :126-128
[10]   MODIFICATION OF THE CYSTEAMINE SIDE-CHAIN OF THIENAMYCIN .3. [J].
SATO, M ;
TAKEMURA, M ;
ATARASHI, S ;
HIGASHI, K ;
NAGAHARA, T ;
FURUKAWA, M ;
IKEUCHI, T ;
OSADA, Y .
JOURNAL OF ANTIBIOTICS, 1987, 40 (09) :1292-1302
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