Michael/Michael Addition Cascade of 2-Benzylidene-1-indanones with Chalcones: Synthesis and Biological Evaluations of Novel Polycyclic Compounds

GEZEGEN H., TUTAR U., Hepokur C., Tuzun G., Atioglu Z., AKKURT M.

CHEMISTRYSELECT, vol.6, no.36, pp.9625-9631, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 6 Issue: 36
  • Publication Date: 2021
  • Doi Number: 10.1002/slct.202102738
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Page Numbers: pp.9625-9631
  • Keywords: Antibacterial, Anticancer, 2-Benzylidene-1-indanone, Chalcone, Michael addition
  • Erciyes University Affiliated: Yes

Abstract

A series of novel racemic 2-aryloyl-1,3-diaryl-2,3,3a,8a-tetrahydrocyclopenta[a]inden-8(1H)-one derivatives were synthesized from KOtBu mediated Michael/Michael addition reaction of 2-benzylidene-1-indanones with chalcones in high yields. This method provides an efficient route for the synthesis of a new class of polycyclic compounds have five stereo centers. The obtained polycyclic compounds were evaluated for the antimicrobial and anticancer activities against fifteen microorganism and three cell lines. The compound 3 r have the best activity value against the cells (MCF-7 IC50=18.01 +/- 0.39 mu g/mL) (MDA-MB- 231 IC50=18.78 +/- 1.75 mu g/mL) (MCF-10 A IC50=31.31 +/- 0.05 mu g/mL).