Synthesis and Biological Applications of New Pyrano[3,2-c]quinolinone Derivatives

Abstract

Pyranoquinolinones were synthesized and subjected to nitration followed by reduction to produce 3-aminopyrano[3,2-c]quinoline-2,5-diones. A series of novel pyranoquinolinone-based Schiff bases were designed and synthesized. They were evaluated for topoisomerase IIβ (TOP2B) inhibitory activity against breast cancer cell line (MCF-7) for the development of novel anticancer agents. A molecular docking study was employed to investigate their binding and functional properties as TOP2B inhibitors, using the DISCOVERY STUDIO 2.5 software. Also, these amines were utilized to obtain a new interesting family of 2,5-dialkyloxazolopyrano[3,2- c]quinolinone derivatives. They were investigated for antitumor activity against different human cancer cell lines (HepG-2, MCF-7 and HCT-116). 3- Amino-N-ethyl-pyranoquinoline-2,5-diones precursor was used to afford novel heteroannulated tetracyclic systems fused to pyranoquinolinone at face c, such as oxazole, oxazine and pyrazine. Structures of the newly synthesized products have been deduced on the basis of their spectral analyses IR, 1H NMR, 13C NMR, Mass and ESI. Keywords: Molecular Docking, Schiff bases, pyrane, quinolone, topoisomerase, antitumor agents, oxazole, oxazine, pyrazine