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Literature DB >> 20392638

Exploration of the HDAC2 foot pocket: Synthesis and SAR of substituted N-(2-aminophenyl)benzamides.

Jerome C Bressi¹, Andy J Jennings, Robert Skene, Yiqin Wu, Robert Melkus, Ron De Jong, Shawn O'Connell, Charles E Grimshaw, Marc Navre, Anthony R Gangloff.

Abstract

A series of N-(2-amino-5-substituted phenyl)benzamides (3-21) were designed, synthesized and evaluated for their inhibition of HDAC2 and their cytotoxicity in HCT116 cancer cells. Multiple compounds from this series demonstrated time-dependent binding kinetics that is rationalized using a co-complex crystal structure of HDAC2 and N-(4-aminobiphenyl-3-yl)benzamide (6). Copyright 2010 Elsevier Ltd. All rights reserved.

Entities: Chemical Disease Gene

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Year: 2010 PMID： 20392638 DOI： 10.1016/j.bmcl.2010.03.091

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

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Cited

81 in total

1. Design, synthesis, modeling, biological evaluation and photoaffinity labeling studies of novel series of photoreactive benzamide probes for histone deacetylase 2.

Authors: Aditya Sudheer Vaidya; Bhargava Karumudi; Emma Mendonca; Antonett Madriaga; Hazem Abdelkarim; Richard B van Breemen; Pavel A Petukhov
Journal: Bioorg Med Chem Lett Date: 2012-06-18 Impact factor: 2.823

2. Extending Cross Metathesis To Identify Selective HDAC Inhibitors: Synthesis, Biological Activities, and Modeling.

Authors: Samuel Bouchet; Camille Linot; Dusan Ruzic; Danica Agbaba; Benoit Fouchaq; Joëlle Roche; Katarina Nikolic; Christophe Blanquart; Philippe Bertrand
Journal: ACS Med Chem Lett Date: 2019-05-09 Impact factor: 4.345

3. Histone deacetylase (HDAC) inhibitor kinetic rate constants correlate with cellular histone acetylation but not transcription and cell viability.

Authors: Benjamin E L Lauffer; Robert Mintzer; Rina Fong; Susmith Mukund; Christine Tam; Inna Zilberleyb; Birgit Flicke; Allegra Ritscher; Grazyna Fedorowicz; Roxanne Vallero; Daniel F Ortwine; Janet Gunzner; Zora Modrusan; Lars Neumann; Christopher M Koth; Patrick J Lupardus; Joshua S Kaminker; Christopher E Heise; Pascal Steiner
Journal: J Biol Chem Date: 2013-07-29 Impact factor: 5.157

4. Metalloprotein-inhibitor binding: human carbonic anhydrase II as a model for probing metal-ligand interactions in a metalloprotein active site.

Authors: David P Martin; Zachary S Hann; Seth M Cohen
Journal: Inorg Chem Date: 2013-05-24 Impact factor: 5.165

5. A chimeric SERM-histone deacetylase inhibitor approach to breast cancer therapy.

Authors: Hitisha K Patel; Marton I Siklos; Hazem Abdelkarim; Emma L Mendonca; Aditya Vaidya; Pavel A Petukhov; Gregory R J Thatcher
Journal: ChemMedChem Date: 2013-08-16 Impact factor: 3.466

6. Active, phosphorylated fingolimod inhibits histone deacetylases and facilitates fear extinction memory.

Authors: Nitai C Hait; Laura E Wise; Jeremy C Allegood; Megan O'Brien; Dorit Avni; Thomas M Reeves; Pamela E Knapp; Junyan Lu; Cheng Luo; Michael F Miles; Sheldon Milstien; Aron H Lichtman; Sarah Spiegel
Journal: Nat Neurosci Date: 2014-05-25 Impact factor: 24.884

Exploration of the HDAC2 foot pocket: Synthesis and SAR of substituted N-(2-aminophenyl)benzamides.

1. Design, synthesis, modeling, biological evaluation and photoaffinity labeling studies of novel series of photoreactive benzamide probes for histone deacetylase 2.

2. Extending Cross Metathesis To Identify Selective HDAC Inhibitors: Synthesis, Biological Activities, and Modeling.

3. Histone deacetylase (HDAC) inhibitor kinetic rate constants correlate with cellular histone acetylation but not transcription and cell viability.

4. Metalloprotein-inhibitor binding: human carbonic anhydrase II as a model for probing metal-ligand interactions in a metalloprotein active site.

5. A chimeric SERM-histone deacetylase inhibitor approach to breast cancer therapy.

6. Active, phosphorylated fingolimod inhibits histone deacetylases and facilitates fear extinction memory.

Review 7. Structure, mechanism, and inhibition of the zinc-dependent histone deacetylases.

8. Entropy as a Driver of Selectivity for Inhibitor Binding to Histone Deacetylase 6.

9. Computational exploration of zinc binding groups for HDAC inhibition.

10. Optimal Substrate-Trapping Mutants to Discover Substrates of HDAC1.