The Infra-red Spectra of Complex Molecules.

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The alkaloids: chemistry and pharmacology. Volume 43.

Nitro group is one of the most important functional groups in organic syntheses because its strongly electron-withdrawing ability activates the scaffold, facilitating the reaction with nucleophilic reagents or the Diels-Alder reaction. In this review, recent progress in the nitro-promoted direct functionalization of pyridones and quinolones is highlighted to complement previous reviews.

Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones.

HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2‑quinolinones using recyclable catalyst

Due to the ever‐increasing antimicrobial resistance there is an urgent need to continuously design and develop novel antimicrobial agents. Inspired by the broad antibacterial activities of various heterocyclic compounds such as 2‐quinolone derivatives, we designed and synthesized new methyl‐(2‐oxo‐1,2‐dihydroquinolin‐4‐yl)‐L‐alaninate‐1,2,3‐triazole derivatives via 1,3‐dipolar cycloaddition reaction of 1‐propargyl‐2‐quinolone‐L‐alaninate with appropriate azide groups. The synthesized compounds were obtained in good yield ranging from 75 to 80 %. The chemical structures of these novel hybrid molecules were determined by spectroscopic methods and the antimicrobial activity of the compounds was investigated against both bacterial and fungal strains. The tested compounds showed significant antimicrobial activity and weak to moderate antifungal activity. Despite the evident similarity of the quinolone moiety of our compounds with fluoroquinolones, our compounds do not function by inhibiting DNA gyrase. Computational characterization of the compounds shows that they have attractive physicochemical and pharmacokinetic properties and could serve as templates for developing potential antimicrobial agents for clinical use.

https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/cmdc.202100714

Design, Synthesis, in vitro and in silico Characterization of 2‐Quinolone‐L‐alaninate‐1,2,3‐triazoles as Antimicrobial Agents

A series of quaternary salts were obtained by reacting 3-(4-bromoacetylphenyl)-1-methylquinolin-2(1H)-one with Py, 4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine. Derivatives of thiazole, imidazo[1,2-a]pyridine, and imidazo[1,2-a]pyrimidine were produced using dinucleophilic reagents. Several of the synthesized compounds possessed high antimicrobial activity, indicating that further research on this series of compounds was promising.

Synthesis and Antimicrobial Activity of 3-Phenyl-1-Methylquinolin-2-One Derivatives

The Meerwein reaction of 1-methylquinolin-2(1H)-one with 4-acetylbenzenediazonium chloride gave 3-(4-acetylphenyl)-1-methylquinolin-2(1H)-one which was brominated to 3-[4-(2-bromoacetyl)phenyl]-1-methylquinolin-2(1H)-one. The latter reacted with pyridine, 4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine to afford the corresponding quaternary salts, and its reactions with thioacetamide, thiourea, 2-aminopyridine, and 2-aminopyrimidine led to the corresponding thiazole, imidazo[1,2-a]pyridine, and imidazo[1,2-a]pyrimidine derivatives containing a 2-oxoquinoline fragment. 3-(4-{2-[2-(Arylmethylidene)-hydrazinyl]-1,3-thiazol-4-yl}phenyl)-1-methylquinolin-2(1H)-ones were obtained by condensation of 3-[4-(2-bromoacetyl)phenyl]-1-methylquinolin-2(1H)-one with thiosemicarbazide and aromatic aldehydes.

Synthesis of nitrogen-containing heterocycles on the basis of 3-(4-acetylphenyl)-1-methylquinolin-2(1 H )-one

Reactions of 4-(4-bromoacetylphenyl)-3-hydroxy-2H-chromen-2-one with Py, 4-methylpyridine, quinoline, and benzo[f]quinoline produced quaternary salts; with dinucleophiles, derivatives of thiazole, imidazo[1,2-a]pyridine, and imidazo[1,2-a]pyrimidine. Several of the target compounds exhibited high antimicrobial activity that indicated further research on these compounds is warranted.

Kh. E. Pitkovych

Papers

Synthesis and Antimicrobial Activity of 3-Phenyl-1-Methylquinolin-2-One Derivatives

Synthesis of nitrogen-containing heterocycles on the basis of 3-(4-acetylphenyl)-1-methylquinolin-2(1 H )-one

Synthesis and Antimicrobial Activity of 4-(4-Acetylphenyl)-3-Hydroxy-2H-Chromen-2-One Derivatives