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Literature DB >> 20171886

Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit.

Kristopher E Boyle¹, Karen S MacMillan, David A Ellis, James P Lajiness, William M Robertson, Dale L Boger.

Abstract

The design, synthesis and evaluation of methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) derivatives are detailed representing analogs of duocarmycin SA containing an oxazole replacement for the fused pyrrole found in the alkylation subunit. Copyright 2010 Elsevier Ltd. All rights reserved.

Entities: CellLine Chemical Disease Gene Species

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Year: 2010 PMID： 20171886 PMCID： PMC2965170 DOI： 10.1016/j.bmcl.2010.01.145

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

40 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. Duocarmycin SA, a new antitumor antibiotic from Streptomyces sp.

Authors: M Ichimura; T Ogawa; K Takahashi; E Kobayashi; I Kawamoto; T Yasuzawa; I Takahashi; H Nakano
Journal: J Antibiot (Tokyo) Date: 1990-08 Impact factor: 2.649

4. Systematic exploration of the structural features of yatakemycin impacting DNA alkylation and biological activity.

Authors: Mark S Tichenor; Karen S MacMillan; John D Trzupek; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal: J Am Chem Soc Date: 2007-08-11 Impact factor: 15.419

5. 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

6. Molecular basis for sequence-specific DNA alkylation by CC-1065.

Authors: L H Hurley; C S Lee; J P McGovren; M A Warpehoski; M A Mitchell; R C Kelly; P A Aristoff
Journal: Biochemistry Date: 1988-05-17 Impact factor: 3.162

7. CC-1065 (NSC 298223), a potent new antitumor agent improved production and isolation, characterization and antitumor activity.

Authors: D G Martin; C Biles; S A Gerpheide; L J Hanka; W C Krueger; J P McGovren; S A Mizsak; G L Neil; J C Stewart; J Visser
Journal: J Antibiot (Tokyo) Date: 1981-09 Impact factor: 2.649

8. Rational design, synthesis, and evaluation of key analogues of CC-1065 and the duocarmycins.

Authors: Mark S Tichenor; Karen S MacMillan; James S Stover; Scott E Wolkenberg; Maria G Pavani; Lorenzo Zanella; Abdel N Zaid; Gianpiero Spalluto; Thomas J Rayl; Inkyu Hwang; Pier Giovanni Baraldi; Dale L Boger
Journal: J Am Chem Soc Date: 2007-10-19 Impact factor: 15.419

2. 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.

Authors: Prem B Chanda; Kristopher E Boyle; Daniel M Brody; Vyom Shukla; Dale L Boger
Journal: Bioorg Med Chem Date: 2016-04-26 Impact factor: 3.641

3. 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

3 in total