Design, synthesis, and biological evaluation of novel 4,4-difluoro-1-methyl-N, 6-diphenyl-5, 6-dihydro-4H-pyrimido [4, 5-b] [1, 2, 4] triazolo [4, 3-d] [1, 4] diazepin-8-amine derivatives as potential BRD4 inhibitors

Chem Biol Drug Des. 2021 May;97(5):1117-1128. doi: 10.1111/cbdd.13833. Epub 2021 Mar 6.

Abstract

Bromodomain-containing protein 4 (BRD4) plays an extremely important physiological role in cancer, and the BRD4 inhibitors can effectively inhibit the proliferation of tumor cells. By taking BI-2536 (PLK1 and BRD4 inhibitor) as the lead compound, sixteen novel BRD4 inhibitors with the 4,4-difluoro-1-methyl-N,6-diphenyl-5,6-dihydro-4H-pyrimido[4,5-b] [1,2,4] triazolo[4,3-d] [1,4] diazepine-8-amine structure were designed and synthetized. Among the target compounds, compound 15h exhibited outstanding inhibition for BRD4-BD1 (IC50 value of 0.42 μM) in the BRD4-BD1 inhibitory activity assay. Additionally, cell growth inhibition assay demonstrated that compound 15h potently suppressed the proliferation of MV4-11 cells (IC50 value of 0.51 μM). Besides, compound 15h induced apoptosis and G0/G1 cycle arrest in MV4-11 leukemia cells effectively, and downregulated the expression of c-Myc in a dose-dependent manner. In summary, the optimal compound 15h is expected to become the clinical therapeutic drug for further research.

Keywords: BRD4 inhibitors; anti-proliferation; anti-tumor; c-Myc; cell apoptosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Binding Sites
  • Cell Cycle Proteins / antagonists & inhibitors*
  • Cell Cycle Proteins / metabolism
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Down-Regulation / drug effects
  • Drug Design*
  • G1 Phase Cell Cycle Checkpoints / drug effects
  • Humans
  • Molecular Docking Simulation
  • Proto-Oncogene Proteins c-myc / metabolism
  • Structure-Activity Relationship
  • Transcription Factors / antagonists & inhibitors*
  • Transcription Factors / metabolism
  • Triazoles / chemistry*
  • Triazoles / metabolism
  • Triazoles / pharmacology

Substances

  • Amines
  • Antineoplastic Agents
  • BRD4 protein, human
  • Cell Cycle Proteins
  • Proto-Oncogene Proteins c-myc
  • Transcription Factors
  • Triazoles