Literature DB >> 27759399

Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor.

Cheng Zhang1, C James Chou2.   

Abstract

A novel synthetic approach to amidoquinones by the reaction of n class="Chemical">naphthoquinones with hydroxamic acids under basic conditions was developed. The reaction is mild and operationally simple, and it affords high yields of amidoquinones. With this new method, a novel, very strong HDAC6 inhibitor, which showed high toxicity to AML cells, was successfully synthesized.

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Year:  2016        PMID: 27759399      PMCID: PMC5242401          DOI: 10.1021/acs.orglett.6b02740

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  40 in total

1.  New Synthetic Technology for the Construction of N-Containing Quinones and Derivatives Thereof: Total Synthesis of Epoxyquinomycin B We thank Dr. D. H. Huang, Dr. G. Siuzdak, and Dr. R. Chadha for NMR spectroscopic, mass spectrometric, and X-ray crystallographic assistance, respectively. Financial support for this work was provided by The Skaggs Institute for Chemical Biology, the National Institutes of Health (USA), a predoctoral fellowship from the National Science Foundation (P.B.), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-LaRoche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.

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2.  A novel class of small molecule inhibitors of HDAC6.

Authors:  Elizabeth S Inks; Benjamin J Josey; Sean R Jesinkey; C James Chou
Journal:  ACS Chem Biol       Date:  2011-11-11       Impact factor: 5.100

3.  Salinisporamycin, a novel metabolite from Salinispora arenicola. [corrected].

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4.  An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols.

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Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.005

Review 5.  Transition metal-catalyzed N-arylations of amidines and guanidines.

Authors:  Tom R M Rauws; Bert U W Maes
Journal:  Chem Soc Rev       Date:  2012-01-05       Impact factor: 54.564

6.  Pd-catalyzed α-selective C(sp3)-H acetoxylation of amides through an unusual cyclopalladation mechanism.

Authors:  Meining Wang; Yang Yang; Zhoulong Fan; Zhen Cheng; Weiliang Zhu; Ao Zhang
Journal:  Chem Commun (Camb)       Date:  2015-02-21       Impact factor: 6.222

Review 7.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Synthesis of biaryl tertiary amines through Pd/norbornene joint catalysis in a remote C-H amination/Suzuki coupling reaction.

Authors:  Changqing Ye; Hui Zhu; Zhiyuan Chen
Journal:  J Org Chem       Date:  2014-09-09       Impact factor: 4.354

9.  Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors:  Scott N Mlynarski; Alexander S Karns; James P Morken
Journal:  J Am Chem Soc       Date:  2012-09-24       Impact factor: 15.419

10.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

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  1 in total

1.  The one-pot synthesis of amidonapthoquinones from aminonaphthoquinones.

Authors:  Jinya Yin; Jon D Rainier
Journal:  Tetrahedron Lett       Date:  2020-03-04       Impact factor: 2.415

  1 in total

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