Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study

Molecules. 2015 Dec 15;20(12):22520-33. doi: 10.3390/molecules201219863.

Abstract

Amination of the 2-aryl-6-bromo-4-chloro-8-iodoquinazolines with 2-aminoethanol followed by acid-promoted cyclodehydration of the incipient 2-((6,8-dihalo-2-phenylquinazolin-4-yl)amino)ethanols afforded the corresponding novel 5-aryl-9-bromo-7-iodo-2,3-dihydro-2H-imidazo[1,2-c]quinazolines. The latter were, in turn, subjected to sequential (Sonogashira and Suzuki-Miyaura) and one-pot two-step (Sonogashira/Stille) cross-coupling reactions to afford diversely functionalized polycarbo-substituted 2H-imidazo[1,2-c]quinazolines. The imidazoquinazolines were screened for in vitro cytotoxicity against human breast adenocarcinoma (MCF-7) cells and human cervical cancer (HeLa) cells.

Keywords: cross-coupling; cytotoxicity; dihalogenated 2H-imidazo[1,2-c]quinazolines; imidazo[1,2-c]quinazolines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Imidazoles / chemical synthesis*
  • Imidazoles / pharmacology
  • Inhibitory Concentration 50
  • MCF-7 Cells
  • Quinazolines / chemical synthesis*
  • Quinazolines / pharmacology

Substances

  • Antineoplastic Agents
  • Imidazoles
  • Quinazolines