Manganese(III) Acetate-Based Radical Cyclization Reactions for Pyranocoumarin and Pyranoquinoline Compounds: Synthesis, DFT and Molecular Docking Studies

YAKUT M., YILMAZ M., Pekel T., ERKAN S., Katirci R., Bicer E.

CHEMISTRYSELECT, cilt.7, sa.44, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 7 Sayı: 44
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1002/slct.202202787
  • Dergi Adı: CHEMISTRYSELECT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Anahtar Kelimeler: Cyclization, Manganese(III), Pyranocoumarin, Pyranoquinoline, Radical, CERIUM(IV) AMMONIUM-NITRATE, FLUORINATED 1,3-DICARBONYL COMPOUNDS, OXIDATIVE CYCLIZATION, ALKENES, DERIVATIVES, 3-OXOPROPANENITRILES, DIENES, DIHYDROFURANS, 2-THIENYL, AMIDES
  • Kocaeli Üniversitesi Adresli: Evet

Özet

Pyranofuroquinoline and pyranofurocoumarin derivatives are significant class of compounds due to being useful in many diverse applications. The synthesis of the compounds are succeeded in one step by radical cyclization reaction in the presence of manganese(III) acetate. Furoquinoline and furocoumarin reactants were used together with 1,1-disubstituted-, 1,2-disubstituted and cyclic alkenes giving pyranofuroquinoline and pyranofurocoumarin compounds in moderate to high yields. Also, we were able to isolate alkenyl and acetoxy- side-products in minor low yields. The electronic and optical features of furoquinoline and furocoumarin reactants and pyranofuroquinoline products were inquired using theoretical approaches (DFT and TD-DFT). Their excitation and emission spectrums were computed. The results revealed that the pyranofuroquinoline molecules did not show the energy transfer feature. It was observed that the behavior of nonlinear optic of furoquinoline is higher than the pyranofuroquinoline and furocoumarin molecules. But the average polarization and the anisotropy of the polarizability of pyranofuroquinoline increased and was found to be 262.7 and 141.9 respectively. Also, according to the calculated docking parameters, the investigated pyranofuroquinoline and pyranofurocoumarin compounds were found to have higher activity than the substances with anticancer and antibacterial standards.