NEW 5-NITROIMIDAZOLES BEARING LACTAME NUCLEUS - SYNTHESIS AND ANTIBACTERIAL PROPERTIES

被引:40
作者
JENTZER, O
VANELLE, P
CROZET, MP
MALDONADO, J
BARREAU, M
机构
[1] FAC PHARM MARSEILLE,CHIM ORGAN LAB,27 BD JEAN MOULIN,F-13385 MARSEILLE 5,FRANCE
[2] RHONE POULENC RORER CTR RECH VITRY,F-94403 VITRY,FRANCE
[3] FAC SCI & TECH ST JEROME,CHIM ORGAN LAB B,CNRS,URA 1412,F-13397 MARSEILLE 13,FRANCE
关键词
5-NITROIMIDAZOLES; SRN1; REACTION; LACTAMS; ANTIBACTERIAL AGENTS; ANTIANAEROBIC ACTIVITY;
D O I
10.1016/0223-5234(91)90118-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
New 5-nitroimidazoles bearing a trisubstituted ethylenic double bond in position 2 were prepared by reacting various 1-alkyl-2-chloromethyl-5-nitroimidazole with 3-nitrolactam anions by S(RN)1 mechanism in phase-transfer catalysis conditions. These compounds showed in vitro and in vivo antianaerobic activity which was clearly greater than that of metronidazole. Structure-activity relationships have been discussed.
引用
收藏
页码:687 / 697
页数:11
相关论文
共 29 条
[1]   ENZYME-INHIBITION BY NITRO AND NITROSO-COMPOUNDS [J].
ALSTON, TA ;
PORTER, DJT ;
BRIGHT, HJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (11) :418-424
[2]   CHEMICAL REACTIONS OF CAPROLACTAM [J].
BENSON, RE ;
CAIRNS, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (06) :2115-2118
[3]   CLEAVAGE OF ETHERS [J].
BHATT, MV ;
KULKARNI, SU .
SYNTHESIS-STUTTGART, 1983, (04) :249-282
[4]   SYNTHESIS OF 2-AZETIDINONES (BETA-LACTAMS) [J].
BLICKE, FF ;
GOULD, WA .
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (08) :1102-1107
[5]  
Breccia A., 1982, NITROIMIDAZOLES CHEM
[6]  
CHEMERDA JM, 1971, Patent No. 3584007
[7]  
COSAR C, 1966, ARZNEI-FORSCHUNG, V16, P23
[8]   CNDO/S METHOD INTERPRETATION OF ULTRAVIOLET-SPECTRA OF 4-NITRO AND 5-NITROIMIDAZOLES [J].
CROZET, MP ;
VANELLE, P ;
BOUSCASSE, L ;
AVIGNON, T .
SPECTROSCOPY LETTERS, 1986, 19 (09) :1049-1057
[9]   SRNI-REACTIONS IN A HETEROCYCLIC SERIES .2. REACTIVITY OF 1-METHYL-2-CHLOROMETHYL-5-NITROIMIDAZOLE [J].
CROZET, MP ;
SURZUR, JM ;
VANELLE, P ;
GHIGLIONE, C ;
MALDONADO, J .
TETRAHEDRON LETTERS, 1985, 26 (08) :1023-1026
[10]  
CROZET MP, 1988, CR ACAD SCI II, V306, P967