Literature DB >> 19879753

Synthesis and evaluation of a thio analogue of duocarmycin SA.

Karen S MacMillan1, James P Lajiness, Carlota Lopez Cara, Romeo Romagnoli, William M Robertson, Inkyu Hwang, Pier Giovanni Baraldi, Dale L Boger.   

Abstract

The design, synthesis, and preliminary evaluation of methyl 1,2,8,8a-tetrahydrocyclopropa[c]thieno[3,2-e]indol-4-one-6-carboxylate (CTI) derivatives are detailed representing a single atom change (N to S) embedded in the duocarmycin SA alkylation subunit.

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Year:  2009        PMID： 19879753      PMCID： PMC2784222          DOI： 10.1016/j.bmcl.2009.10.063

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


  35 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

2.  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

3.  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

4.  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

5.  Stereoelectronic factors influencing the biological activity and DNA interaction of synthetic antitumor agents modeled on CC-1065.

Authors:  M A Warpehoski; I Gebhard; R C Kelly; W C Krueger; L H Li; J P McGovren; M D Prairie; N Wicnienski; W Wierenga
Journal:  J Med Chem       Date:  1988-03       Impact factor: 7.446

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

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.  Total synthesis and evaluation of iso-duocarmycin SA and iso-yatakemycin.

Authors:  Karen S MacMillan; Trinh Nguyen; Trihn Nguyen; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419
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  6 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.  Preclinical pharmacology of novel indolecarboxamide ML-970, an investigative anticancer agent.

Authors:  Elizabeth Rayburn; Wei Wang; Mao Li; Xu Zhang; Hongxia Xu; Haibo Li; Jiang-Jiang Qin; Lee Jia; Joseph Covey; Moses Lee; Ruiwen Zhang
Journal:  Cancer Chemother Pharmacol       Date:  2012-02-25       Impact factor: 3.333

3.  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

4.  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

5.  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

Review 6.  Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis.

Authors:  Erika A Crane; Karl Gademann
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336
  6 in total

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