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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.