SYNTHESIS AND PRELIMINARY EVALUATION OF (+)-CBI-INDOLE2 - AN ENHANCED FUNCTIONAL ANALOG OF (+)-CC-1065

被引:59
作者
BOGER, DL
ISHIZAKI, T
SAKYA, SM
MUNK, SA
KITOS, PA
JIN, Q
BESTERMAN, JM
机构
[1] UNIV KANSAS,DEPT BIOCHEM,LAWRENCE,KS 66045
[2] GLAXO RES INST,DEPT CELL BIOL,RES TRIANGLE PK,NC 27709
关键词
D O I
10.1016/S0960-894X(00)80243-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis and comparative preliminary evaluation of (+)-CBI-indole2 (3) are detailed in efforts that further demonstrate a direct relationship between the chemical stability of the agents and their biological potency/DNA alkylation intensity.
引用
收藏
页码:115 / 120
页数:6
相关论文
共 17 条
[1]   A DEMONSTRATION OF THE INTRINSIC IMPORTANCE OF STABILIZING HYDROPHOBIC BINDING AND NONCOVALENT VANDERWAALS CONTACTS DOMINANT IN THE NONCOVALENT CC-1065/B-DNA BINDING [J].
BOGER, DL ;
INVERGO, BJ ;
COLEMAN, RS ;
ZARRINMAYEH, H ;
KITOS, PA ;
THOMPSON, SC ;
LEONG, T ;
MCLAUGHLIN, LW .
CHEMICO-BIOLOGICAL INTERACTIONS, 1990, 73 (01) :29-52
[2]   SYNTHESIS OF N-(TERT-BUTYLOXYCARBONYL)-CBI, CBI, CBI-CDPI1, AND CBI-CDPI2 - ENHANCED FUNCTIONAL ANALOGS OF CC-1065 INCORPORATING THE 1,2,9,9A-TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL-4-ONE (CBI) LEFT-HAND SUBUNIT [J].
BOGER, DL ;
ISHIZAKI, T ;
KITOS, PA ;
SUNTORNWAT, O .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5823-5832
[3]   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 [J].
BOGER, DL ;
ISHIZAKI, T .
TETRAHEDRON LETTERS, 1990, 31 (06) :793-796
[4]   SYNTHESIS AND EVALUATION OF ABORTED AND EXTENDED CC-1065 FUNCTIONAL ANALOGS - (+)-CPI-PDE-I1, AND (-)-CPI-PDE-I1, (+)-CPI-PDE-I1, AND (-)-CPI-CDPI1, AND (+/-)-CPI-PDE-I1, (+)-CPI-PDE-I1, AND (-)-CPI-CDPI3 - PREPARATION OF KEY PARTIAL STRUCTURES AND DEFINITION OF AN ADDITIONAL FUNCTIONAL-ROLE OF THE CC-1065 CENTRAL AND RIGHT-HAND SUBUNITS [J].
BOGER, DL ;
COLEMAN, RS ;
INVERGO, BJ ;
SAKYA, SM ;
ISHIZAKI, T ;
MUNK, SA ;
ZARRINMAYEH, H ;
KITOS, PA ;
THOMPSON, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4623-4632
[5]   SYNTHESIS OF N-(PHENYLSULFONYL)-CI, N-((TERT-BUTYLOXY)CARBONYL)-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 ;
ISHIZAKI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5230-5240
[6]   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
[7]   DUOCARMYCIN PYRINDAMYCIN DNA ALKYLATION PROPERTIES AND IDENTIFICATION, SYNTHESIS, AND EVALUATION OF AGENTS INCORPORATING THE PHARMACOPHORE OF THE DUOCARMYCIN PYRINDAMYCIN ALKYLATION SUBUNIT - IDENTIFICATION OF THE CC-1065-DUOCARMYCIN COMMON PHARMACOPHORE [J].
BOGER, DL ;
ISHIZAKI, T ;
ZARRINMAYEH, H ;
MUNK, SA ;
KITOS, PA ;
SUNTORNWAT, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) :8961-8971
[10]  
BOGER DL, IN PRESS J AM CHEM S