Duocarmycin SA Shortened, Simplified, and Extended Agents: A Systematic Examination of the Role of the DNA Binding Subunit
- 1 May 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 119 (21), 4977-4986
- https://doi.org/10.1021/ja9637208
Abstract
No abstract availableKeywords
This publication has 30 references indexed in Scilit:
- pH Dependence of the rate of DNA alkylation for (+)-duocarmycin SA and (+)-CCBI-TMIBioorganic & Medicinal Chemistry Letters, 1997
- Examination of the role of the duocarmycin SA methoxy substituents: Identification of the minimum, fully potent DNA binding subunitBioorganic & Medicinal Chemistry Letters, 1996
- A comparative study of the solvolysis reactivity, regioselectivity, and stereochemistry of the duocarmycin a and sa alkylation subunitsBioorganic & Medicinal Chemistry Letters, 1996
- Synthesis, Chemical Properties, and Preliminary Evaluation of Substituted CBI Analogs of CC-1065 and the Duocarmycins Incorporating the 7-Cyano-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one Alkylation Subunit: Hammett Quantitation of the Magnitude of Electronic Effects on Functional ReactivityThe Journal of Organic Chemistry, 1996
- Duocarmycins, Potent Antitumor Antibiotics Produced by Streptomyces sp. Structures and Chemistry.CHEMICAL & PHARMACEUTICAL BULLETIN, 1995
- Design, Synthesis, and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 2,3,10,10a-Tetrahydro-1H-cyclopropa[d]benzo[f]quinol-5-one (CBQ) Alkylation Subunit: Identification and Structural Origin of Subtle Stereoelectronic Features That Govern Reactivity and RegioselectivityJournal of the American Chemical Society, 1994
- (+)-CC-1065 produces bending of DNA that appears to resemble adenine/thymine tractsChemical Research in Toxicology, 1991
- A demonstration of the intrinsic importance of stabilizing hydrophobic binding and non-convalent van der waals contacts dominant in the non-covalent CC-1065/B-DNA bindingChemico-Biological Interactions, 1990
- Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI, (.+-.)-CC-1065, (+)-CC-1065, ent-(-)-CC-1065, and the precise, functional agents (.+-.)-CPI-CDPI2, (+)-CPI-CDPI2, and (-)-CPI-CDPI2 [(.+-.)-(3bR*,4aS*)-, (+)-(3bR,4aS)-, and (-)-(3bS,4aR)-deoxy-CC-1065]Journal of the American Chemical Society, 1988
- Studies on the total synthesis of CC-1065: preparation of a synthetic simplified 3-carbamoyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole dimer/trimer/tetramer (CDPI dimer/trimer/tetramer) and development of methodology for PDE-I dimer methyl ester formationThe Journal of Organic Chemistry, 1987