Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors

Eur J Med Chem. 2017 Jul 7:134:230-241. doi: 10.1016/j.ejmech.2017.04.010. Epub 2017 Apr 12.

Abstract

Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42 nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of α-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases.

Keywords: Cancer; Epigenetics; SIRT2; Sirtuins; Structure-based optimization.

MeSH terms

  • Acetamides / chemistry*
  • Acetamides / pharmacology*
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Breast / drug effects
  • Breast / metabolism
  • Breast Neoplasms / drug therapy*
  • Breast Neoplasms / metabolism
  • Drug Discovery
  • Female
  • Histone Deacetylase Inhibitors / chemistry*
  • Histone Deacetylase Inhibitors / pharmacology*
  • Humans
  • MCF-7 Cells
  • Molecular Docking Simulation
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Sirtuin 2 / antagonists & inhibitors*
  • Sirtuin 2 / metabolism
  • Structure-Activity Relationship
  • Tubulin / metabolism

Substances

  • Acetamides
  • Antineoplastic Agents
  • Histone Deacetylase Inhibitors
  • Pyrimidines
  • Tubulin
  • Sirtuin 2