Synthesis of dihydrooxazole analogues derived from linezolid

被引:8
作者
Einsiedel, J
Schoerner, C
Gmeiner, P
机构
[1] Univ Erlangen Nurnberg, Emil Fischer Ctr, Dept Med Chem, D-91052 Erlangen, Germany
[2] Univ Erlangen Nurnberg, Inst Clin Microbiol Immunol & Hyg, D-91054 Erlangen, Germany
关键词
serine; dihydrooxazoles; antibiotics;
D O I
10.1016/S0040-4020(03)00490-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from (S)-serine, the linezolid analogue 3 with dihydrooxazole partial structure was synthesized and pharmacologically investigated. With the help of MEP comparisons structural requirements for antibacterial activity were evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3403 / 3407
页数:5
相关论文
共 15 条
[1]   REACTIONS OF AN N-SULFONYLAMINE INNER SALT [J].
ATKINS, GM ;
BURGESS, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (17) :4744-&
[2]  
BARBACHYN MR, 1999, Patent No. 9941244
[3]   Interactive SAR studies:: Rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists [J].
Bettinetti, L ;
Schlotter, K ;
Hübner, H ;
Gmeiner, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (21) :4594-4597
[4]   Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-positive bacterial infections [J].
Brickner, SJ ;
Hutchinson, DK ;
Barbachyn, MR ;
Manninen, PR ;
Ulanowicz, DA ;
Garmon, SA ;
Grega, KC ;
Hendges, SK ;
Toops, DS ;
Ford, CW ;
Zurenko, GE .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (03) :673-679
[5]  
Burger A, 1991, Prog Drug Res, V37, P287
[6]   Linezolid is a specific inhibitor of 50S ribosomal subunit formation in Staphylococcus aureus cells [J].
Champney, WS ;
Miller, M .
CURRENT MICROBIOLOGY, 2002, 44 (05) :350-356
[7]   5-ARYL-BETA,GAMMA BUTENOLIDE, A NEW CLASS OF ANTIBACTERIAL DERIVED FROM THE N-ARYL OXAZOLIDINONE DUP-721 [J].
DENIS, A ;
VILLETTE, T .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (16) :1925-1930
[8]   Benzamide bioisosteres incorporating dihydroheteroazole substructures:: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179) [J].
Einsiedel, J ;
Hübner, H ;
Gmeiner, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (18) :2533-2536
[9]   Nitrogen-carbon-linked (azolylphenyl)oxazolidinones with potent antibacterial activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis [J].
Genin, MJ ;
Hutchinson, DK ;
Allwine, DA ;
Hester, JB ;
Emmert, DE ;
Garmon, SA ;
Ford, CW ;
Zurenko, GE ;
Hamel, JC ;
Schaadt, RD ;
Stapert, D ;
Yagi, BH ;
Friis, JM ;
Shobe, EM ;
Adams, WJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (26) :5144-5147
[10]   ANTIBACTERIALS - SYNTHESIS AND STRUCTURE ACTIVITY STUDIES OF 3-ARYL-2-OXOOXAZOLIDINES .2. THE A GROUP [J].
GREGORY, WA ;
BRITTELLI, DR ;
WANG, CLJ ;
KEZAR, HS ;
CARLSON, RK ;
PARK, CH ;
CORLESS, PF ;
MILLER, SJ ;
RAJAGOPALAN, P ;
WUONOLA, MA ;
MCRIPLEY, RJ ;
EBERLY, VS ;
SLEE, AM ;
FORBES, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2569-2578