Literature DB >> 20161204

Synthesis and Preliminary Evaluation of Duocarmycin Analogues Incorporating the 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[2,3-e]indol-4-one (CNI) and 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[1,2-e]indol-4-one (iso-CNI) Alkylation Subunits.

Carla M Gauss1, Akiyuki Hamasaki, Jay P Parrish, Karen S Macmillan, Thomas J Rayl, Inkyu Hwang, Dale L Boger.   

Abstract

Efficient syntheses and a preliminary evaluation of 1,2,11,11a-tetrahydrocyclopropa[c]-naphtho[2,3-e]indole (CNI) and 1,2,11,11a-tetrahydrocyclopropa[c]naphtho[1,2-e]indole (iso-CNI), and their derivatives containing an anthracene and phenanthrene variant of the CC-1065 or duocarmycin alkylation subunit are detailed.

Entities:  

Year:  2009        PMID： 20161204      PMCID： PMC2713043          DOI： 10.1016/j.tet.2009.02.065

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  26 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.  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

7.  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

8.  Establishing the parabolic relationship between reactivity and activity for derivatives and analogues of the duocarmycin and CC-1065 alkylation subunits.

Authors:  Jay P Parrish; Terry V Hughes; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419

Review 9.  CC-1065 and the duocarmycins: unraveling the keys to a new class of naturally derived DNA alkylating agents.

Authors:  D L Boger; D S Johnson
Journal:  Proc Natl Acad Sci U S A       Date:  1995-04-25       Impact factor: 11.205

10.  An additional spirocyclization for duocarmycin SA.

Authors:  Karen S MacMillan; Dale L Boger
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419
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  3 in total

1.  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.

Authors:  Kristopher E Boyle; Karen S MacMillan; David A Ellis; James P Lajiness; William M Robertson; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-02-02       Impact factor: 2.823

2.  Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs.

Authors:  William M Robertson; David B Kastrinsky; Inkyu Hwang; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-03-25       Impact factor: 2.823

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

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