Design, synthesis and antiproliferative activity of 2-acetamidothiazole-5-carboxamide derivatives

Med Chem. 2012 Jul;8(4):587-94. doi: 10.2174/157340612801216418.

Abstract

In order to develop a new series of dual inhibitors of SRC and ABL, and to investigate whether the pyrimidin- 4-ylamino moiety is critical for dasatinib's activity, acetyl substitution was adopted as alternate scaffold at the 2-amino group. Eighteen novel dasatinib derivatives were developed by a parallel synthesis approach and evaluated for their antiproliferative effects. Preliminary tests showed that some of the target compounds IId, IIe and IIf manifested strong antiproliferative activity against MCF-7, MDA-MB 231 and HT-29 cells. Easpecially IId proved to be the most potent compound. Structure-activity relationship studies indicate that the introduction of acetyl substitution as alternate scaffold of pyrimidin-4-ylamino reduced the activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology*
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dasatinib
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • Molecular Structure
  • Neoplasms / drug therapy
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Thiazoles / chemistry
  • Thiazoles / pharmacology

Substances

  • Amides
  • Antineoplastic Agents
  • Carboxylic Acids
  • Pyrimidines
  • Thiazoles
  • Dasatinib