Literature DB >> 22330196

Synthesis of azaphilone-based chemical libraries.

Mathieu Achard1, Aaron B Beeler, John A Porco.   

Abstract

The synthesis of azaphilone scaffolds that have been further diversified by cross coupling acylation and amine addition is reported. Methodology development also led to novel modifications including C5 acetoxylation and condensations producing isoquinolin-6(7H) structures. Overall, the library synthesis afforded three azaphilone sublibraries, including vinylogous pyridones which project diversity elements in four sectors of the azaphilone core.

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Year:  2012        PMID： 22330196      PMCID： PMC3313624          DOI： 10.1021/co300002x

Source DB:  PubMed          Journal:  ACS Comb Sci        ISSN： 2156-8944            Impact factor:   3.784


  15 in total

1.  Discovery of protein phosphatase inhibitor classes by biology-oriented synthesis.

Authors:  Andrea Nören-Müller; Ivan Reis-Corrêa; Heino Prinz; Claudia Rosenbaum; Krishna Saxena; Harald J Schwalbe; Dietmar Vestweber; Guiseppe Cagna; Stefan Schunk; Oliver Schwarz; Hajo Schiewe; Herbert Waldmann
Journal:  Proc Natl Acad Sci U S A       Date:  2006-06-29       Impact factor: 11.205

2.  Asymmetric syntheses of (-)-mitorubrin and related azaphilone natural products.

Authors:  Jianglong Zhu; John A Porco
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

Review 3.  Synthesis of natural product inspired compound collections.

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Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Biology-oriented synthesis of a natural-product inspired oxepane collection yields a small-molecule activator of the Wnt-pathway.

Authors:  Sudipta Basu; Bernhard Ellinger; Stefano Rizzo; Céline Deraeve; Markus Schürmann; Hans Preut; Hans-Dieter Arndt; Herbert Waldmann
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-17       Impact factor: 11.205

5.  Synthesis studies toward chloroazaphilone and vinylogous gamma-pyridones: two common natural product core structures.

Authors:  Wan-Guo Wei; Zhu-Jun Yao
Journal:  J Org Chem       Date:  2005-06-10       Impact factor: 4.354

6.  Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.

Authors:  Loana Musso; Sabrina Dallavalle; Lucio Merlini; Adriana Bava; Gianluca Nasini; Sergio Penco; Giuseppe Giannini; Chiara Giommarelli; Andrea De Cesare; Valentina Zuco; Loredana Vesci; Claudio Pisano; Massimo Castorina; Ferdinando Milazzo; Maria Luisa Cervoni; Fabrizio Dal Piaz; Nunziatina De Tommasi; Franco Zunino
Journal:  Bioorg Med Chem       Date:  2010-07-01       Impact factor: 3.641

7.  Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization.

Authors:  Andrew R Germain; Daniel M Bruggemeyer; Jianglong Zhu; Cedric Genet; Peter O'Brien; John A Porco
Journal:  J Org Chem       Date:  2011-03-14       Impact factor: 4.354

8.  Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization.

Authors:  Jianglong Zhu; Nicholas P Grigoriadis; Jonathan P Lee; John A Porco
Journal:  J Am Chem Soc       Date:  2005-07-06       Impact factor: 15.419

9.  A stabilized formulation of IBX (SIBX) for safe oxidation reactions including a new oxidative demethylation of phenolic methyl aryl ethers.

Authors:  Aurélie Ozanne; Laurent Pouységu; Dominique Depernet; Bruno François; Stéphane Quideau
Journal:  Org Lett       Date:  2003-08-07       Impact factor: 6.005

10.  Efficient access to orthoquinols and their [4 + 2] cyclodimers via SIBX-mediated hydroxylative phenol dearomatization.

Authors:  Nathalie Lebrasseur; Julien Gagnepain; Aurélie Ozanne-Beaudenon; Jean-Michel Léger; Stéphane Quideau
Journal:  J Org Chem       Date:  2007-07-12       Impact factor: 4.354
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  3 in total

1.  Preparation, Structure, and Potent Antifouling Activity of Sclerotioramine Derivatives.

Authors:  Mei-Yan Wei; Cui-Fang Wang; Kai-Ling Wang; Pei-Yuan Qian; Chang-Yun Wang; Chang-Lun Shao
Journal:  Mar Biotechnol (NY)       Date:  2017-07-07       Impact factor: 3.619

Review 2.  Azaphilone alkaloids: prospective source of natural food pigments.

Authors:  Lujie Liu; Zhilong Wang
Journal:  Appl Microbiol Biotechnol       Date:  2021-12-18       Impact factor: 4.813

3.  Identification and characterization of the chaetoviridin and chaetomugilin gene cluster in Chaetomium globosum reveal dual functions of an iterative highly-reducing polyketide synthase.

Authors:  Jaclyn M Winter; Michio Sato; Satoru Sugimoto; Grace Chiou; Neil K Garg; Yi Tang; Kenji Watanabe
Journal:  J Am Chem Soc       Date:  2012-10-19       Impact factor: 15.419
  3 in total

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