Literature DB >> 17311393

Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue.

Shijun Wen1, Krystle L Carey, Yoichi Nakao, Nobuhiro Fusetani, Graham Packham, A Ganesan.   

Abstract

The unprecedented diastereoselective Mannich reaction of a Z-allylsulfoximine was a key step in the total synthesis of the marine natural products azumamide A and E, and an unnatural analogue. Their relative potency as histone deacetylase inhibitors was evaluated and found to correlate with predicted zinc-binding affinity. [reaction: see text]

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Year:  2007        PMID： 17311393     DOI： 10.1021/ol070046y

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


  8 in total

Review 1.  Macrocyclic histone deacetylase inhibitors.

Authors:  Sandra C Mwakwari; Vishal Patil; William Guerrant; Adegboyega K Oyelere
Journal:  Curr Top Med Chem       Date:  2010       Impact factor: 3.295

Review 2.  An overview of naturally occurring histone deacetylase inhibitors.

Authors:  Bumki Kim; Jiyong Hong
Journal:  Curr Top Med Chem       Date:  2015       Impact factor: 3.295

3.  Isoform-selective HDAC1/6/8 inhibitors with an imidazo-ketopiperazine cap containing stereochemical diversity.

Authors:  Bertrand Lecointre; Remy Narozny; Maria Teresa Borrello; Johanna Senger; Alokta Chakrabarti; Manfred Jung; Martin Marek; Christophe Romier; Jelena Melesina; Wolfgang Sippl; Laurent Bischoff; A Ganesan
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2018-06-05       Impact factor: 6.237

4.  Design, synthesis, biological evaluation, and structural characterization of potent histone deacetylase inhibitors based on cyclic alpha/beta-tetrapeptide architectures.

Authors:  Ana Montero; John M Beierle; Christian A Olsen; M Reza Ghadiri
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

5.  Synthesis and histone deacetylase inhibitory activity of largazole analogs: alteration of the zinc-binding domain and macrocyclic scaffold.

Authors:  Albert A Bowers; Nathan West; Tenaya L Newkirk; Annie E Troutman-Youngman; Stuart L Schreiber; Olaf Wiest; James E Bradner; Robert M Williams
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

6.  Discovery of potent and selective histone deacetylase inhibitors via focused combinatorial libraries of cyclic alpha3beta-tetrapeptides.

Authors:  Christian A Olsen; M Reza Ghadiri
Journal:  J Med Chem       Date:  2009-12-10       Impact factor: 7.446

7.  Preparation and Applications of 4-Methoxybenzyl Esters in Organic Synthesis.

Authors:  Kyle T Howard; John D Chisholm
Journal:  Org Prep Proced Int       Date:  2016-01-29       Impact factor: 1.628

8.  Synthesis and conformation-activity relationships of the peptide isosteres of FK228 and largazole.

Authors:  Albert A Bowers; Thomas J Greshock; Nathan West; Guillermina Estiu; Stuart L Schreiber; Olaf Wiest; Robert M Williams; James E Bradner
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419
  8 in total

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