Literature DB >> 18205373

Improved total synthesis of the potent HDAC inhibitor FK228 (FR-901228).

Thomas J Greshock1, Deidre M Johns, Yasuo Noguchi, Robert M Williams.   

Abstract

A scaleable synthesis of the potent histone deacetylase (HDAC) inhibitor FK228 is described. A reliable strategy for preparing the key beta-hydroxy mercapto heptenoic acid partner was accomplished in nine steps and 13% overall yield. A Noyori asymmetric hydrogen-transfer reaction established the hydroxyl stereochemistry in >99:1 er via the reduction of a propargylic ketone.

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Year:  2008        PMID： 18205373      PMCID： PMC3097137          DOI： 10.1021/ol702957z

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


  16 in total

1.  Total synthesis of RK-397.

Authors:  Scott E Denmark; Shinji Fujimori
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

2.  The first biologically active synthetic analogues of FK228, the depsipeptide histone deacetylase inhibitor.

Authors:  Alexander Yurek-George; Alexander Richard Liam Cecil; Alex Hon Kit Mo; Shijun Wen; Helen Rogers; Fay Habens; Satoko Maeda; Minoru Yoshida; Graham Packham; A Ganesan
Journal:  J Med Chem       Date:  2007-10-24       Impact factor: 7.446

3.  FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties, and antitumor activity.

Authors:  H Ueda; H Nakajima; Y Hori; T Fujita; M Nishimura; T Goto; M Okuhara
Journal:  J Antibiot (Tokyo)       Date:  1994-03       Impact factor: 2.649

4.  FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. II. Structure determination.

Authors:  N Shigematsu; H Ueda; S Takase; H Tanaka; K Yamamoto; T Tada
Journal:  J Antibiot (Tokyo)       Date:  1994-03       Impact factor: 2.649

5.  Asymmetric Samarium-Reformatsky Reaction of Chiral alpha-Bromoacetyl-2-oxazolidinones with Aldehydes.

Authors: 
Journal:  J Org Chem       Date:  2000-03-24       Impact factor: 4.354

6.  Inhibitors of human histone deacetylase: synthesis and enzyme and cellular activity of straight chain hydroxamates.

Authors:  Stacy W Remiszewski; Lidia C Sambucetti; Peter Atadja; Kenneth W Bair; Wendy D Cornell; Michael A Green; Kobporn Lulu Howell; Manfred Jung; Paul Kwon; Nancy Trogani; Heather Walker
Journal:  J Med Chem       Date:  2002-02-14       Impact factor: 7.446

7.  Histone deacetylase inhibitors--a new tool to treat cancer.

Authors:  Raz Somech; Shai Izraeli; Amos J Simon
Journal:  Cancer Treat Rev       Date:  2004-08       Impact factor: 12.111

8.  Total synthesis of the depsipeptide FR-901375.

Authors:  Yanping Chen; Celine Gambs; Yoshito Abe; Paul Wentworth; Kim D Janda
Journal:  J Org Chem       Date:  2003-11-14       Impact factor: 4.354

9.  Total synthesis of spiruchostatin A, a potent histone deacetylase inhibitor.

Authors:  Alexander Yurek-George; Fay Habens; Matthew Brimmell; Graham Packham; A Ganesan
Journal:  J Am Chem Soc       Date:  2004-02-04       Impact factor: 15.419

10.  Structurally simple trichostatin A-like straight chain hydroxamates as potent histone deacetylase inhibitors.

Authors:  Soon Hyung Woo; Sylvie Frechette; Elie Abou Khalil; Giliane Bouchain; Arkadii Vaisburg; Naomy Bernstein; Oscar Moradei; Silvana Leit; Martin Allan; Marielle Fournel; Marie-Claude Trachy-Bourget; Zuomei Li; Jeffrey M Besterman; Daniel Delorme
Journal:  J Med Chem       Date:  2002-06-20       Impact factor: 7.446
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  12 in total

Review 1.  Microbial natural products: molecular blueprints for antitumor drugs.

Authors:  Lesley-Ann Giddings; David J Newman
Journal:  J Ind Microbiol Biotechnol       Date:  2013-09-03       Impact factor: 3.346

Review 2.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

Review 3.  Chromobacterium violaceum and its important metabolites--review.

Authors:  M Durán; A Faljoni-Alario; N Durán
Journal:  Folia Microbiol (Praha)       Date:  2011-01-21       Impact factor: 2.099

Review 4.  Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma.

Authors:  Karen M VanderMolen; William McCulloch; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Antibiot (Tokyo)       Date:  2011-05-18       Impact factor: 2.649

Review 5.  Histone deacetylase inhibitors: the epigenetic therapeutics that repress hypoxia-inducible factors.

Authors:  Shuyang Chen; Nianli Sang
Journal:  J Biomed Biotechnol       Date:  2010-12-05

6.  Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor.

Authors:  Albert Bowers; Nathan West; Jack Taunton; Stuart L Schreiber; James E Bradner; Robert M Williams
Journal:  J Am Chem Soc       Date:  2008-07-19       Impact factor: 15.419

7.  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.  FK228 Analogues Induce Fetal Hemoglobin in Human Erythroid Progenitors.

Authors:  Levi Makala; Salvatore Di Maro; Tzu-Fang Lou; Sharanya Sivanand; Jung-Mo Ahn; Betty S Pace
Journal:  Anemia       Date:  2012-05-14

9.  The histone deacetylase inhibitor, romidepsin, as a potential treatment for pulmonary fibrosis.

Authors:  Franco Conforti; Elizabeth R Davies; Claire J Calderwood; Thomas H Thatcher; Mark G Jones; David E Smart; Sumeet Mahajan; Aiman Alzetani; Tom Havelock; Toby M Maher; Philip L Molyneaux; Andrew J Thorley; Teresa D Tetley; Jane A Warner; Graham Packham; A Ganesan; Paul J Skipp; Benjamin J Marshall; Luca Richeldi; Patricia J Sime; Katherine M A O'Reilly; Donna E Davies
Journal:  Oncotarget       Date:  2017-07-25

10.  Genomics-guided discovery of a new and significantly better source of anticancer natural drug FK228.

Authors:  Xiangyang Liu; Feng Xie; Leah B Doughty; Qi Wang; Lixin Zhang; Xueting Liu; Yi-Qiang Cheng
Journal:  Synth Syst Biotechnol       Date:  2018-11-05
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