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Abstract Pyranoquinolinediones were synthesized and subjected to nitration followed by reduction to produce a novel 3-aminopyrano[3,2-c]quinoline-2,5- diones. Structure of compound 3c has been investigated and confirmed by 2D – NMR (gCOSY, gHSQC and gHMBC). Anti-oxidant and anti-cancer activity with molecular docking of 3-aminopyranoquinolinones has been evaluated. 3-amino-N- butyl-pyranoquinoline-2,5-diones precursor was utilized to obtain some novel heteroannulated pyrano[3,2-c]quinolone derivatives. These heteroannulation reactions afforded novel heterocyclic systems fused to pyranoquinolinone at face c, such as oxazole, triazine and pyrazine. A series of interesting Schiff bases and azo dyes derivatives of pyranoquinolinone were synthesized. Keywords: Quinolinone, Pyranoquinolinone, Molecular docking, Heteroannulated tetracyclic systems, Oxazolo, antioxidant, anticancer, Spectral analysis. Supervisors: Prof. Dr. Mustafa Mohamed Ismail Professor of Organic chemistry, Department of chemistry, Faculty of Education, Ain shams University Prof. Dr. Alaa Alden Salem Professor of analytical chemistry, Department of chemistry, Faculty of Faculty of Science – UAEU Asst.Dr. Hany Mohamed Hassanin Assistant Professor of Organic chemistry, Department of chemistry, Faculty of Education, Ain shams University Asst.Dr. Ibram Mahmoud Abdou Associate Professor of Organic chemistry, Department of chemistry, Faculty of Faculty of Science – UAEU |