Alkyl-substituted N-methylaryl-N'-aryl-4-aminobenzamides: A new series of small molecule inhibitors for Wip1 phosphatase

Eur J Med Chem. 2022 Dec 5:243:114763. doi: 10.1016/j.ejmech.2022.114763. Epub 2022 Sep 18.

Abstract

The wild-type p53 induced phosphatase 1 (Wip1), a member of the serine/threonine-specific PP2C family, is overexpressed in numerous human cancers. Wip1 dephosphorylates p53 as well as several kinases (such as p38 MAPK, ATM, Chk1, and Chk2) in the DNA damage response pathway that are responsible for maintaining genomic stability and preventing oncogenic transformation. As a result, Wip1 is an attractive target for synthetic inhibitors that could be further developed into therapeutics to treat some cancers. In this study, we report a series of alkyl-substituted N-methylaryl-N'-aryl-4-aminobenzamides and their inhibitory activity of the Wip1 phosphatase. A straightforward synthetic route was developed to synthesize the target compounds from commercially available starting materials. Three different portions (R1, R2, R3) of the core scaffold were extensively modified to examine structure-activity relationships. This study revealed interesting trends about a new molecular scaffold to inhibit Wip1.

Keywords: Aminobenzamides; Cancer treatment; Cross coupling; Phosphate; Small molecule inhibitors; Wip1 phosphatase.

MeSH terms

  • DNA Damage
  • Humans
  • Phosphoprotein Phosphatases* / genetics
  • Phosphoprotein Phosphatases* / metabolism
  • Phosphorylation
  • Protein Phosphatase 2C / genetics
  • Protein Phosphatase 2C / metabolism
  • Protein Serine-Threonine Kinases
  • Tumor Suppressor Protein p53* / metabolism

Substances

  • Protein Phosphatase 2C
  • Phosphoprotein Phosphatases
  • Tumor Suppressor Protein p53
  • 4-aminobenzamide
  • Protein Serine-Threonine Kinases