A POTENT, SIMPLE DERIVATIVE OF AN ANALOG OF THE CC-1065 ALKYLATION SUBUNIT

被引：40

作者：

BOGER, DL ^{[1
]}

ISHIZAKI, T ^{[1
]}

ZARRINMAYEH, H ^{[1
]}

KITOS, PA ^{[1
]}

SUNTORNWAT, O ^{[1
]}

机构：

[1] UNIV KANSAS,DEPT BIOCHEM,LAWRENCE,KS 66045

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1991年 / 1卷 / 01期

关键词：

D O I：

10.1016/S0960-894X(01)81090-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A simple semicarbazide derivative of CBI, an analog of the authentic CPI alkylation subunit of CC-1065, exhibits enhanced in vitro cytotoxic potency and DNA alkylation properties (ca. 100x) derived from noncovalent electrostatic DNA binding.

引用

页码：55 / 58

页数：4

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

[8] 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

[9]

BOGER DL, IN PRESS P NATL ACAD

[10]

BOGER DL, 1991, IN PRESS TETRAHEDRON, V47

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