Literature DB >> 27221071

Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) alkylation subunit.

Prem B Chanda1, Kristopher E Boyle1, Daniel M Brody1, Vyom Shukla1, Dale L Boger2.   

Abstract

The design, synthesis, and evaluation of methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) derivatives are detailed representing analogs of duocarmycin SA and yatakemycin containing an imidazole replacement for the fused pyrrole found in the DNA alkylation subunit.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  CC-1065; DNA alkylation; Duocarmycin; Yatakemycin

Mesh：

Substances：

Year:  2016        PMID： 27221071      PMCID： PMC5052114          DOI： 10.1016/j.bmc.2016.04.050

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  39 in total

1.  CC-1065 and the Duocarmycins: Synthetic Studies.

Authors:  Dale L. Boger; Christopher W. Boyce; Robert M. Garbaccio; Joel A. Goldberg
Journal:  Chem Rev       Date:  1997-05-08       Impact factor: 60.622

Review 2.  Mechanisms of in situ activation for DNA-targeting antitumor agents.

Authors:  Scott E Wolkenberg; Dale L Boger
Journal:  Chem Rev       Date:  2002-07       Impact factor: 60.622

3.  The DNA phosphate backbone is not involved in catalysis of the duocarmycin and CC-1065 DNA alkylation reaction.

Authors:  Yves Ambroise; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2002-02-11       Impact factor: 2.823

4.  Metal cation complexation and activation of reversed CPyI analogues of CC-1065 and duocarmycin SA: partitioning the effects of binding and catalysis.

Authors:  D A Ellis; S E Wolkenberg; D L Boger
Journal:  J Am Chem Soc       Date:  2001-09-26       Impact factor: 15.419

5.  Resolution of a CPzI precursor, synthesis and biological evaluation of (+) and (-)-N-Boc-CPzI: a further validation of the relationship between chemical solvolytic stability and cytotoxicity.

Authors:  P G Baraldi; B Cacciari; R Romagnoli; G Spalluto; C W Boyce; D L Boger
Journal:  Bioorg Med Chem Lett       Date:  1999-11-01       Impact factor: 2.823

6.  Preparation of benzene, furan, and thiophene analogs of duocarmycin SA employing a newly-devised phenol-forming reaction.

Authors:  H Muratake; A Hayakawa; M Natsume
Journal:  Chem Pharm Bull (Tokyo)       Date:  2000-10       Impact factor: 1.645

7.  Yatakemycin, a novel antifungal antibiotic produced by Streptomyces sp. TP-A0356.

Authors:  Yasuhiro Igarashi; Katsuyuki Futamata; Tsuyoshi Fujita; Akira Sekine; Hisato Senda; Hideo Naoki; Tamotsu Furumai
Journal:  J Antibiot (Tokyo)       Date:  2003-02       Impact factor: 2.649

8.  Selective metal cation activation of a DNA alkylating agent: synthesis and evaluation of methyl 1,2,9, 9a-Tetrahydrocyclopropa[c]pyrido[3,2-e]indol-4-one-7-carboxylate (CPyI).

Authors:  D L Boger; C W Boyce
Journal:  J Org Chem       Date:  2000-06-30       Impact factor: 4.354

Review 9.  Duocarmycins--natures prodrugs?

Authors:  Mark Searcey
Journal:  Curr Pharm Des       Date:  2002       Impact factor: 3.116

10.  Copper- and palladium-catalyzed intramolecular aryl guanidinylation: an efficient method for the synthesis of 2-aminobenzimidazoles.

Authors:  Ghotas Evindar; Robert A Batey
Journal:  Org Lett       Date:  2003-01-23       Impact factor: 6.005
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  1 in total

1.  The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.

Authors:  Dale L Boger
Journal:  J Org Chem       Date:  2017-10-13       Impact factor: 4.354
  1 in total

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