Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl-and pyranochromen-2-one derivatives

Karam Chand, Amir Nasrolahi Shirazi, Preeti Yadav, Rakesh K. Tiwari, Meena Kumari, Keykavous Parang, Sunil K. Sharma

Research output: Contribution to journalArticle

Abstract

A series of 6-and 8-cinnamoylchromen-2-one and dihydropyranochromen-2-one derivatives were synthesized and their antiproliferative activities were evaluated against three human cancer cell lines, i.e., ovarian adenocarcinoma (SK-OV-3), leukemia (CCRF-CEM), and breast carcinoma (MCF-7). In general, 8-cinnamoylchromen-2-one derivatives were found to have higher antiproliferative activity against the cancer cells when compared with 6-cinnamoyl analogues. Among all of the hybrid chromen-2-one-chalcone/flavanone compounds, a 7-hydroxy-8-cinnamoylchromen-2-one derivative 35 was found to be consistently active against all the cancer cell lines and inhibited the cell proliferation of SK-OV-3, CCRF-CEM, and MCF-7 by 63%, 50%, and 43%, respectively, at a concentration of 50 μmol/L after 72 h of incubation. This compound also exhibited the highest Src kinase inhibition (IC50 = 14.5 μmol/L). Structure-activity relationship studies provided insights for designing the next generation of chromen-2-one-chalcone hybrid prototypes and the development of new leads as anticancer agents and (or) Src kinase inhibitors.

Original languageEnglish (US)
Pages (from-to)741-754
Number of pages14
JournalCanadian Journal of Chemistry
Volume91
Issue number8
DOIs
StatePublished - Aug 2013
Externally publishedYes

Keywords

  • Anticancer
  • Antiproliferative
  • C-Src kinase
  • Chromen-2-one

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Catalysis

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