Stereoselective synthesis of β-lactams with polyaromatic imines:: Entry to new and novel anticancer agents

被引:194
作者
Banik, I [1 ]
Becker, FF [1 ]
Banik, BK [1 ]
机构
[1] Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
关键词
D O I
10.1021/jm0255825
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
We present herein stereoselective symthesis of novel beta-lactams using polyaromatic imines following the Staudinger reaction. Consistent mechanisms for these results have been advanced. As a measure of cytotaxicity, some of these compounds have been assayed against nine human cancer cell lines. Structure-activity study has revealed that 1-N-chrysenyl and 1-N-phenanthrenyl 3-acetoxy-4-aryl-2-azetidinones have potent anticancer activity. The presence of the acetoxy group at C-3 of the beta-lactams has proven to be obligatory for their anticancer activity
引用
收藏
页码:12 / 15
页数:4
相关论文
共 43 条
[21]   Polyhydroxy amino acid derivatives via β-lactams using enantiospecific approaches and microwave techniques [J].
Bose, AK ;
Banik, BK ;
Mathur, C ;
Wagle, DR ;
Manhas, MS .
TETRAHEDRON, 2000, 56 (31) :5603-5619
[22]   STEREOCONTROL OF BETA-LACTAM FORMATION USING MICROWAVE IRRADIATION [J].
BOSE, AK ;
BANIK, BK ;
MANHAS, MS .
TETRAHEDRON LETTERS, 1995, 36 (02) :213-216
[23]  
BOSE AK, 2000, AMIDE LINKAGE SELECT, P157
[24]   2-AZETIDINONES AS INHIBITORS OF CHOLESTEROL ABSORPTION [J].
BURNETT, DA ;
CAPLEN, MA ;
DAVIS, HR ;
BURRIER, RE ;
CLADER, JW .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1733-1736
[25]   7-alkylidenecephalosporin esters as inhibitors of human leukocyte elastase [J].
Buynak, JD ;
Rao, AS ;
Ford, GP ;
Carver, C ;
Adam, G ;
Geng, B ;
Bachmann, B ;
Shobassy, S ;
Lackey, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (21) :3423-3433
[26]   2-azetidinone cholesterol absorption inhibitors: Structure-activity relationships on the heterocyclic nucleus [J].
Clader, JW ;
Burnett, DA ;
Caplen, MA ;
Domalski, MS ;
Dugar, S ;
Vaccaro, W ;
Sher, R ;
Browne, ME ;
Zhao, HR ;
Burrier, RE ;
Salisbury, B ;
Davis, HR .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) :3684-3693
[27]   A SEMIEMPIRICAL THEORETICAL-STUDY ON THE FORMATION OF BETA-LACTAMS FROM KETENES AND IMINES [J].
COSSIO, FP ;
UGALDE, JM ;
LOPEZ, X ;
LECEA, B ;
PALOMO, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :995-1004
[28]   CHIRAL CONTROL IN THE STAUDINGER REACTION BETWEEN KETENES AND IMINES - A THEORETICAL SCF-MO STUDY ON ASYMMETRIC TORQUOSELECTIVITY [J].
COSSIO, FP ;
ARRIETA, A ;
LECEA, B ;
UGALDE, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2085-2093
[29]   NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .1. SYNTHESIS OF O-2-ISOCEPHAMS [J].
DOYLE, TW ;
BELLEAU, B ;
LUH, BY ;
FERRARI, CF ;
CUNNINGHAM, MP .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (03) :468-483
[30]   SYNTHETIC INHIBITORS OF ELASTASE [J].
EDWARDS, PD ;
BERNSTEIN, PR .
MEDICINAL RESEARCH REVIEWS, 1994, 14 (02) :127-194