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, cilt.6, sa.36, ss.9625-9631, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 6 Sayı: 36
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1002/slct.202102738
  • Dergi Adı: CHEMISTRYSELECT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Sayfa Sayıları: ss.9625-9631
  • Anahtar Kelimeler: Antibacterial, Anticancer, 2-Benzylidene-1-indanone, Chalcone, Michael addition, ENANTIOSELECTIVE MICHAEL ADDITION, ALTERNATE METHOD, DIMERIZATION, DERIVATIVES
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

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).