Synthetic Approaches and Biological Evaluation of Some Novel 3,4-Disubstituted Quinolin-2(1H)-one Derivatives

Abstract

Reactivity of 3-acetyl-4-methylthioquinolin-2(1H)-one (3) towards various nitrogen and carbon nucleophiles such as 1,2- or 1,4-dinucleophiles and active methylene compounds has been studied under different reaction conditions. It was found that the nature of products is extremely dependent on both reactivity of the reagent, pH media and other ambient conditions. Also, the chemical behavior of compound 3 towards different electrophilic reactions such as chlorination, brominations, iodinations, nitration and oxidation were carried out to afford novel quinolinone derivatives bearing different substituents. Structures of the synthesized products have been deduced on the basis of their spectral analyses. New substituted quinolinones were screened for their biological activities in which some products indicated significant antimicrobial, antioxidant, antitumor activities and toxicity. Also, some selected quinoline derivatives were theoretically studied via DFT calculations. Keywords: Quinolinone, Nucleophilic condensation, Electrophilic substitution, Heterocyclization, Biological applications, Spectral analyses. Supervisors: Prof. Dr. Mohamed Abass Mohamed Professor of Organic Chemistry, Department of Chemistry, Faculty of Education, Ain Shams University. Asst.Dr. Hany Mohamed Hassanin Assistant Professor of Organic Chemistry, Department of Chemistry, Faculty of Education, Ain Shams University. Asst.Dr. Hassan Abdallah Allimony Assistant Professor of Organic Chemistry, Department of Chemistry, Faculty of Education, Ain Shams University. Dr. Asmaa Ismail Nabil Lecturer of Biochemistry, Department of Chemistry, Faculty of Education, Ain Shams University