Development of novel chromeno[4,3-c]pyrazol-4(2H)-one derivates containing piperazine as inhibitors of PI3Kα

Bioorg Chem. 2019 Nov:92:103238. doi: 10.1016/j.bioorg.2019.103238. Epub 2019 Aug 30.

Abstract

PI3K pathway has been heavily studied and is one of the most potential targets for various cancer treatment. Herein, we designed and synthesized a series of novel chromeno[4,3-c]pyrazol-4(2H)-one derivates contained piperazine based on our previous research. They were evaluated for their PI3Kα wild-type and H1047R mutant inhibitory activities and anticancer effects in vitro. Most of these compounds displayed the potential antiproliferative activities against four cancer cell lines (HCT-116, A549, Huh7 and HL60). Among them, Compound 4p revealed the remarkable antiproliferative activity and was selected for further biological evaluation. Compound 4p displayed the potent activity against both PI3Kα wild-type and H1047R mutant, and a certain degree of selectivity for PI3Kα over PI3Kβ, γ and δ, and meanwhile it can remarkable down-regulate the phosphorylation of Akt. In addition, compound 4p was found to induce cell apoptosis via upregulation of Bax and cleaved-caspase 3/9, and downregulation of Bcl-2. The above results suggested that compound 4p could be considered as a promising PI3Kα inhibitor.

Keywords: Antitumor; Chromeno[4,3-c]pyrazol-4(2H)-one derivates; PI3Kα; Selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • A549 Cells
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Cell Proliferation / drug effects
  • Chromones / chemistry*
  • HCT116 Cells
  • HL-60 Cells
  • Humans
  • Molecular Docking Simulation
  • Molecular Structure
  • Phosphatidylinositol 3-Kinases / metabolism*
  • Phosphoinositide-3 Kinase Inhibitors / chemical synthesis*
  • Phosphoinositide-3 Kinase Inhibitors / chemistry
  • Phosphoinositide-3 Kinase Inhibitors / pharmacology
  • Piperazine / chemistry*

Substances

  • Antineoplastic Agents
  • Chromones
  • Phosphoinositide-3 Kinase Inhibitors
  • chromeno(4,3-c)pyrazol-4-one
  • Piperazine