Discovery of (S)- N-(2-Amino-4-fluorophenyl)-4-(1-(3-(4-((dimethylamino)methyl)phenyl)-6-oxopyridazin-1(6 H)-yl)ethyl)benzamide as Potent Class I Selective HDAC Inhibitor for Oral Anticancer Drug Candidate

J Med Chem. 2023 May 25;66(10):7016-7037. doi: 10.1021/acs.jmedchem.3c00525. Epub 2023 May 15.

Abstract

A novel series of benzamide derivatives were successively designed and synthesized prepared from the pyridazinone scaffold. Among them, (S)-17b, demonstrated potent inhibitory activity in vitro toward human class I HDAC isoforms and human myelodysplastic syndrome (SKM-1) cell line. Also, (S)-17b strongly increased the intracellular level of acetyl-histone H3 and P21 simultaneously and effectively induced G1 cell cycle arrest and apoptosis. Through oral dosing in SKM-1 xenograft models, (S)-17b exhibited excellent in vivo antitumor activity. In addition, compound (S)-17b showed better antitumor efficacy on mouse models with intact immune system than those with thymus deficiencies. Furthermore, this compound displayed a favorable pharmacokinetic profile in ICR mice and SD rat, respectively, minimal metabolic property differences among hepatocytes from five species, and a low inhibition upon the human ether-a-go-go (hERG) channel with an IC50 value of 34.6 μΜ. This novel compound (S)-17b may serve as a new drug candidate for further investigation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents* / pharmacokinetics
  • Antineoplastic Agents* / therapeutic use
  • Apoptosis
  • Benzamides / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation
  • Disease Models, Animal
  • Drug Screening Assays, Antitumor
  • Histone Deacetylase Inhibitors* / pharmacokinetics
  • Histone Deacetylase Inhibitors* / therapeutic use
  • Humans
  • Mice
  • Mice, Inbred ICR
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship

Substances

  • Histone Deacetylase Inhibitors
  • Antineoplastic Agents
  • Benzamides