Synthesis and biological evaluation of some novel hetroaryl quinolinone derivatives

Abstract

The aim of this study involves the synthesis of novel heterocyclic scaffolds containing quinoline moiety and studying their role as antimicrobial agents. 4‐hydroxy‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,5(6H))‐dione (1) was utilized as a precursor for the construction of new polyheterocyclic ring systems. It reacted with three aryl and (heteroaryl) aldehydes to furnish the corresponding arylidenes 2a‐c. The nucleophilic cyclization of compound 2 with hydrazine hydrate to give pyrazolyl quinolinone 3. Moreover, the reaction of 1 with HCHO/morpholine led to the formation of the adduct 7. The synthesized N‐(5–3‐formyl‐4‐hydroxy‐6‐phenyl‐2,5‐dioxo‐5,6‐dihydro‐2H‐pyrano [3,2‐c] quinoline (10) was utilized for the synthesis of 3‐(([aryl]amino)methylene)‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,4,5 (3H,6H)‐trione 11a‐c via its treatment with three types of amines. Treatment of 1 with POCl3/Et3N afforded the corresponding 4‐chloro derivative 20. Which upon treatment with thiourea lead to the formation of the corresponding 4‐mercapto derivative 21. The latter 21 was alkylated using ethylbromo acetate giving 22. All freshly synthesized scaffolds were elucidated by considering the data of both elemental and spectral analyses. The synthesized scaffolds were screened for antimicrobial activities also showed promising results. The p‐chlorobenzylidene pyrazolylquinolone derivative 3 has excellent antimicrobial properties against Proteus vulgaris compared to its mild activity against Staph aureus. While 4‐Chloro‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,5(6H)‐dione (20) exhibited good activates against Staph aureus surpassing the activity of reference antibiotic. Also, compounds 21 showed excellent antifungal activity against Candida albicans higher than fluconazole.

Novel NO2 semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

“…Pyrano[3,2‐ c ]quinoline derivatives exist in many natural alkaloids [ 1 ] and have a diversity of pharmacological activities including antitumor, [ 2 ] anticancer, [ 3 ] anti‐diabetic, [ 4 ] anti‐coronavirus, [ 5 ] antihypertensive, [ 6 ] antitubercular, [ 7 ] antimalarial, [ 8 ] antibacterial, [ 9 ] antimicrobial, [ 10 ] as well as photodiode fabrication, [ 11 ] thin films, [ 12,13 ] optical applications, [ 14 ] and corrosion inhibitors. [ 15 ] Metal complexes of ligands containing quinoline moiety have attracted particular interest because of their biological activities.…”

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

“…As an active against Staph aureus, it was found to be superior to the reference antibiotic. The antifungal activity of analogue 5 was superior to fluconazole in the treatment of Candida albicans [57]. R. Watpade et al have published the synthesis of various pyranoquinolone analogues.…”

“…Abd El‐Ghani et al published a method for constructing novel pyranoquinolone analogues with the intention of demonstrating good biological functions [57]. Antimicrobial properties of new heterocyclic scaffolds including quinolines are the focus of this research.…”