Synthesis and biological evaluation of coumarincarboxylic acids as inhibitors of gyrase B. L-rhamnose as an effective substitute for L-noviose

被引:46
作者
Ferroud, D
Collard, J
Klich, M
Dupuis-Hamelin, C
Mauvais, P
Lassaigne, P
Bonnefoy, A
Musicki, B
机构
[1] Hoechst Marion Roussel, Med Chem, F-93235 Romainville, France
[2] Hoechst Marion Roussel, Infect Dis, F-93235 Romainville, France
关键词
D O I
10.1016/S0960-894X(99)00493-X
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of novobiocin-like coumarincarboxylic acids has been prepared bearing the L-rhamnosyl moiety as the sugar portion of the molecule. The similar DNA gyrase inhibitory activity of the novel class of coumarins to that of novobiocin demonstrates that L-rhamnose can effectively replace L-noviose. Introduction of alkyl side-chains at C-5 of coumarin leads to improved in vitro antibacterial properties in the novel series. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2881 / 2886
页数:6
相关论文
共 27 条
[1]  
ARISAWA M, 1992, Patent No. 18490
[2]   Design, synthesis and evaluation of a novel series of spiroketals based on the structure of the antibacterial gyrase inhibitor novobiocin [J].
Bell, W ;
Block, MH ;
Cook, C ;
Grant, JA ;
Timms, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (18) :2789-2801
[3]  
Chartreaux F., 1999, Patent Application, Patent No. [894805, EP 894805]
[4]   ORTHO METALATION DIRECTED BY ALPHA-AMINO ALKOXIDES [J].
COMINS, DL ;
BROWN, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :1078-1083
[5]  
GEIWIZ J, 1995, Patent No. 675122
[6]  
Godfrey J C, 1972, Adv Appl Microbiol, V15, P231, DOI 10.1016/S0065-2164(08)70094-7
[7]  
GOETSCHI E, 1994, J PHARM THER, V60, P367
[8]   STRUCTURAL STUDIES ON STREPTONIVICIN, A NEW ANTIBIOTIC [J].
HOEKSEMA, H ;
JOHNSON, JL ;
HINMAN, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (24) :6710-6711
[9]   COBALT(II) CHLORIDE CATALYZED ACYLATION OF ALCOHOLS WITH ACETIC-ANHYDRIDE - SCOPE AND MECHANISM [J].
IQBAL, J ;
SRIVASTAVA, RR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2001-2007
[10]   CYCLOTHIALIDINE, A NOVEL DNA GYRASE INHIBITOR .2. ISOLATION, CHARACTERIZATION AND STRUCTURE ELUCIDATION [J].
KAMIYAMA, T ;
SHIMMA, N ;
OHTSUKA, T ;
NAKAYAMA, N ;
ITEZONO, Y ;
NAKADA, N ;
WATANABE, J ;
YOKOSE, K .
JOURNAL OF ANTIBIOTICS, 1994, 47 (01) :37-45