RESOLUTION OF A CBI PRECURSOR AND INCORPORATION INTO THE SYNTHESIS OF (+)-CBI, (+)-CBI-CDPI1, (+)-CBI-CDPI2 - ENHANCED FUNCTIONAL ANALOGS OF (+)-CC-1065 - A CRITICAL-APPRAISAL OF A PROPOSED RELATIONSHIP BETWEEN ELECTROPHILE REACTIVITY, DNA-BINDING PROPERTIES, AND CYTOTOXIC POTENCY

被引：84
作者：
BOGER, DL
ISHIZAKI, T
机构：
[1] Department of Chemistry, Purdue University, West Lafayette
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 06期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1016/S0040-4039(00)94629-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Details of the resolution of an immediate CBI precursor, (+)- and (-)-8, and its subsequent incorporation into (+)- and (-)-CBI-CDPIn, optically-active enhanced functional analogs of (+)-CC-1065, are described. In marked contrast to a previously detailed direct relationship between electrophile reactivity and cytotoxic potency, an inverse relationship between the properties is detailed. © 1990.
引用
收藏
页码：793 / 796
页数：4
相关论文
共 15 条
[1]   TOTAL SYNTHESIS OF (+)-CPI-CDPI2 AND (-)-CPI-CDPI2 - (+)-(3BR,4AS)-DEOXY-CC-1065 AND (-)-(3BS,4AR)-DEOXY-CC-1065 [J].
BOGER, DL ;
COLEMAN, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :695-698
[2]   TOTAL SYNTHESIS AND EVALUATION OF (+/-)-N-(TERT-BUTYLOXYCARBONYL)-CBI, (+/-)-CBI-CDPI1, AND (+/-)-CBI-CDPI2 - CC-1065 FUNCTIONAL AGENTS INCORPORATING THE EQUIVALENT 1,2,9,9A-TETRAHYDROCYCLOPROP[1,2-C]BENZ[1,2-E]INDOL-4-ONE (CBI) LEFT-HAND SUBUNIT [J].
BOGER, DL ;
ISHIZAKI, T ;
WYSOCKI, RJ ;
MUNK, SA ;
KITOS, PA ;
SUNTORNWAT, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6461-6463
[3]   STREPTONIGRIN AND LAVENDAMYCIN PARTIAL STRUCTURES - PROBES FOR THE MINIMUM, POTENT PHARMACOPHORE OF STREPTONIGRIN, LAVENDAMYCIN, AND SYNTHETIC QUINOLINE-5,8-DIONES [J].
BOGER, DL ;
YASUDA, M ;
MITSCHER, LA ;
DRAKE, SD ;
KITOS, PA ;
THOMPSON, SC .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) :1918-1928
[4]   TOTAL SYNTHESIS OF (+/-)-N-(PHENYLSULFONYL)-CI AND (+/-)-N-(TERT-BUTYLOXYCARBONYL)-CI, (+/-)-CI-CDPI1, AND (+/-)-CI-CDPI2 - CC-1065 FUNCTIONAL ANALOGS INCORPORATING THE PARENT 1,2,7,7A-TETRAHYDROCYCLOPROP[1,2-C]INDOL-4-ONE (CI) LEFT-HAND SUBUNIT [J].
BOGER, DL ;
WYSOCKI, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1238-1240
[5]   TOTAL SYNTHESIS OF (+/-)-N-2-(PHENYLSULFONYL)-CPI, (+/-)-CC-1065, (+)-CC-1065, ENT-(-)-CC-1065, AND THE PRECISE, FUNCTIONAL AGENTS (+/-)-CPI-CDPI2, (+)-CPI-CDPI2, AND (-)-CPI-CDPI2 [(+/-)-(3BR-STAR,4AS-STAR)-DEOXY-CC-1065, (+)-(3BR,4AS)-DEOXY-CC-1065, AND (-)-(3BS,4AR)-DEOXY-CC-1065] [J].
BOGER, DL ;
COLEMAN, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4796-4807
[6]  
BOGER DL, UNPUB
[7]  
BOGER DL, IN PRESS CHEM BIOL I
[8]  
COLEMAN RS, 1989, STUDIES NATURAL PROD, V3, P301
[9]   COVALENT BINDING OF ANTITUMOR ANTIBIOTICS IN THE MINOR GROOVE OF DNA - MECHANISM OF ACTION OF CC-1065 AND THE PYRROLO(1,4)BENZODIAZEPINES [J].
HURLEY, LH ;
NEEDHAMVANDEVANTER, DR .
ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (08) :230-237
[10]   MOLECULAR-BASIS FOR SEQUENCE-SPECIFIC DNA ALKYLATION BY CC-1065 [J].
HURLEY, LH ;
LEE, CS ;
MCGOVREN, JP ;
WARPEHOSKI, MA ;
MITCHELL, MA ;
KELLY, RC ;
ARISTOFF, PA .
BIOCHEMISTRY, 1988, 27 (10) :3886-3892
12