2-Amino-2,3-dihydro-1 H-indene-5-carboxamide-Based Discoidin Domain Receptor 1 (DDR1) Inhibitors: Design, Synthesis, and in Vivo Antipancreatic Cancer Efficacy

J Med Chem. 2019 Aug 22;62(16):7431-7444. doi: 10.1021/acs.jmedchem.9b00365. Epub 2019 Aug 2.

Abstract

A series of 2-amino-2,3-dihydro-1H-indene-5-carboxamides were designed and synthesized as new selective discoidin domain receptor 1 (DDR1) inhibitors. One of the representative compounds, 7f, bound with DDR1 with a Kd value of 5.9 nM and suppressed the kinase activity with an half-maximal (50%) inhibitory concentration value of 14.9 nM. 7f potently inhibited collagen-induced DDR1 signaling and epithelial-mesenchymal transition, dose-dependently suppressed colony formation of pancreatic cancer cells, and exhibited promising in vivo therapeutic efficacy in orthotopic mouse models of pancreatic cancer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Discoidin Domain Receptor 1 / antagonists & inhibitors*
  • Discoidin Domain Receptor 1 / metabolism
  • Drug Design
  • Epithelial-Mesenchymal Transition / drug effects
  • Humans
  • Male
  • Mice, Inbred C57BL
  • Neoplasms, Experimental / metabolism
  • Neoplasms, Experimental / prevention & control*
  • Pancreatic Neoplasms / metabolism
  • Pancreatic Neoplasms / prevention & control*
  • Rats, Sprague-Dawley
  • Tumor Stem Cell Assay
  • Xenograft Model Antitumor Assays / methods*

Substances

  • Antineoplastic Agents
  • Discoidin Domain Receptor 1