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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1991年 / 1卷 / 02期

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

页码：115 / 120

页数：6

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
BOGER, DL
INVERGO, BJ
COLEMAN, RS
ZARRINMAYEH, H
KITOS, PA
THOMPSON, SC
LEONG, T
MCLAUGHLIN, LW
[J]. 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
BOGER, DL
ISHIZAKI, T
KITOS, PA
SUNTORNWAT, O
[J]. 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
BOGER, DL
ISHIZAKI, T
[J]. 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
BOGER, DL
COLEMAN, RS
INVERGO, BJ
SAKYA, SM
ISHIZAKI, T
MUNK, SA
ZARRINMAYEH, H
KITOS, PA
THOMPSON, SC
[J]. 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
BOGER, DL
WYSOCKI, RJ
ISHIZAKI, T
[J]. 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
BOGER, DL
ISHIZAKI, T
WYSOCKI, RJ
MUNK, SA
KITOS, PA
SUNTORNWAT, O
[J]. 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
BOGER, DL
ISHIZAKI, T
ZARRINMAYEH, H
MUNK, SA
KITOS, PA
SUNTORNWAT, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) : 8961 - 8971
[8] 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
BOGER, DL
WYSOCKI, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) : 1238 - 1240
[9] 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]
BOGER, DL
COLEMAN, RS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) : 4796 - 4807
[10] BOGER DL, IN PRESS J AM CHEM S

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