Literature DB >> 18616341

A concise total synthesis of largazole, solution structure, and some preliminary structure activity relationships.

Christopher G Nasveschuk1, Dana Ungermannova, Xuedong Liu, Andrew J Phillips.   

Abstract

A total synthesis of largazole that proceeds in 8 steps from commercial materials is reported, along with some structure-activity relationships. A combination of NMR studies and molecular modeling have also provided a preliminary picture of the conformation of largazole.

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Year:  2008        PMID: 18616341      PMCID: PMC2664405          DOI: 10.1021/ol8013478

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


  10 in total

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2.  A total synthesis of (+/-)-trans-kumausyne.

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Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

3.  The design, synthesis, and evaluation of organ-specific iron chelators.

Authors:  Raymond J Bergeron; Jan Wiegand; James S McManis; Neelam Bharti
Journal:  J Med Chem       Date:  2006-11-30       Impact factor: 7.446

4.  Total synthesis of (+)-cylindramide A.

Authors:  Amy C Hart; Andrew J Phillips
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

Review 5.  Marine natural products: synthetic aspects.

Authors:  Jonathan C Morris; Andrew J Phillips
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6.  Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp.

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7.  Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors:  M Scholl; S Ding; C W Lee; R H Grubbs
Journal:  Org Lett       Date:  1999-09-23       Impact factor: 6.005

8.  Gradient-Selected NOESY-A Fourfold Reduction of the Measurement Time for the NOESY Experiment

Authors: 
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9.  The synthesis of (+)-allopumiliotoxin 323B'.

Authors:  C H Tan; A B Holmes
Journal:  Chemistry       Date:  2001-05-04       Impact factor: 5.236

10.  Total synthesis and molecular target of largazole, a histone deacetylase inhibitor.

Authors:  Yongcheng Ying; Kanchan Taori; Hyoungsu Kim; Jiyong Hong; Hendrik Luesch
Journal:  J Am Chem Soc       Date:  2008-05-29       Impact factor: 15.419

  10 in total
  25 in total

1.  Largazole and analogues with modified metal-binding motifs targeting histone deacetylases: synthesis and biological evaluation.

Authors:  Pravin Bhansali; Christin L Hanigan; Robert A Casero; L M Viranga Tillekeratne
Journal:  J Med Chem       Date:  2011-10-10       Impact factor: 7.446

Review 2.  Discovery and mechanism of natural products as modulators of histone acetylation.

Authors:  Lilibeth A Salvador; Hendrik Luesch
Journal:  Curr Drug Targets       Date:  2012-07       Impact factor: 3.465

Review 3.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

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Review 4.  An overview of naturally occurring histone deacetylase inhibitors.

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

5.  Biological evaluation of new largazole analogues: alteration of macrocyclic scaffold with click chemistry.

Authors:  Xianlin Li; Zhenchao Tu; Hua Li; Chunping Liu; Zheng Li; Qiao Sun; Yiwu Yao; Jinsong Liu; Sheng Jiang
Journal:  ACS Med Chem Lett       Date:  2012-12-05       Impact factor: 4.345

6.  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
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7.  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

8.  Enantioselective total synthesis of (+)-largazole, a potent inhibitor of histone deacetylase.

Authors:  Arun K Ghosh; Sarang Kulkarni
Journal:  Org Lett       Date:  2008-07-29       Impact factor: 6.005

Review 9.  Thiazole and oxazole alkaloids: isolation and synthesis.

Authors:  Danilo Davyt; Gloria Serra
Journal:  Mar Drugs       Date:  2010-11-05       Impact factor: 5.118

10.  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

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