CHIRAL REQUIREMENTS FOR TUMOR PROMOTERS - CONFORMATIONS AND ACTIVITY OF BENZOLACTAMS

被引:14
作者
ENDO, Y
OHNO, M
HIRANO, M
TAKEDA, M
ITAI, A
SHUDO, K
机构
[1] Faculty of Pharmaceutical Sciences, University of Tokyo, Bunkyo-ku, Tokyo, 113
关键词
D O I
10.1016/0960-894X(94)80023-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
(-)-Benzolactam-V8-310 ((-)-1), which reproduces the twist conformation and biological activity of teleocidins, its antipode ((+)-1), and the epi-benzolactams ((-)-2 and (+)-2) were synthesized as optically pure forms. Structure-activity results indicate that the stereochemistry at C-5 plays a critical role in the binding to the receptor(s).
引用
收藏
页码:491 / 494
页数:4
相关论文
共 13 条
[1]  
ENDO Y, 1982, CHEM PHARM BULL, V30, P3457
[2]   SYNTHESIS AND STEREOCHEMISTRY OF INDOLACTAM-V, AN ACTIVE FRAGMENT OF TELEOCIDINS - STRUCTURAL REQUIREMENTS FOR TUMOR-PROMOTING ACTIVITY [J].
ENDO, Y ;
SHUDO, K ;
ITAI, A ;
HASEGAWA, M ;
SAKAI, S .
TETRAHEDRON, 1986, 42 (21) :5905-5924
[3]   POSSIBLE NATURALLY OCCURRING TUMOR PROMOTER, TELEOCIDIN-B FROM STREPTOMYCES [J].
FUJIKI, H ;
MORI, M ;
NAKAYASU, M ;
TERADA, M ;
SUGIMURA, T .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1979, 90 (03) :976-983
[4]   INDOLE ALKALOIDS - DIHYDROTELEOCIDIN-B, TELEOCIDIN, AND LYNGBYATOXIN-A AS MEMBERS OF A NEW CLASS OF TUMOR PROMOTERS [J].
FUJIKI, H ;
MORI, M ;
NAKAYASU, M ;
TERADA, M ;
SUGIMURA, T ;
MOORE, RE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1981, 78 (06) :3872-3876
[5]  
HUBERMAN E, 1979, P NATL ACAD SCI USA, V76, P1293, DOI 10.1073/pnas.76.3.1293
[6]   NEW PROBES FOR RECEPTOR ANALYSIS OF TUMOR PROMOTERS SYNTHESIS OF FLUORESCENT DERIVATIVES OF (-)-INDOLACTAM-V, THE BASIC RING-STRUCTURE OF TELEOCIDINS [J].
IRIE, K ;
HAGIWARA, N ;
KOSHIMIZU, K .
TETRAHEDRON, 1987, 43 (22) :5251-5260
[7]  
JENG AY, 1986, CANCER RES, V46, P1966
[8]   PREDICTION OF RING CONFORMATIONS OF INDOLACTAMS - CRYSTAL AND SOLUTION STRUCTURES [J].
KAWAI, T ;
ICHINOSE, T ;
TAKEDA, M ;
TOMIOKA, N ;
ENDO, Y ;
YAMAGUCHI, K ;
SHUDO, K ;
ITAI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6150-6155
[9]  
KAWAI T, 1992, J MED CHEM, V25, P2248
[10]   A REGIOCONTROLLED AND STEREOCONTROLLED TOTAL SYNTHESIS OF (-)-INDOLACTAM-V [J].
KOGAN, TP ;
SOMERS, TC ;
VENUTI, MC .
TETRAHEDRON, 1990, 46 (19) :6623-6632