Ultrasonication‐Induced Synthesis and Antimicrobial Evaluation of Some Multifluorinated Pyrazolone Derivatives

Abstract

A series of novel fluorine containing pyrazole-pyrazolone (4a–j) and chromone-pyrazolone (5a–i) was synthesized from multifluorinated pyrazolone by the Knoevenagel condensation reaction. All compounds were synthesized by conventional heating as well as ultrasound irradiation technique. It was found that ultrasonication method was more efficient than conventional heating method. The newly synthesized compounds were subjected forin vitroantimicrobial screening against four bacterial pathogens, namely,Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli,andPseudomonas aeruginosaand three fungal pathogensCandida albicans, Aspergillus niger,andAspergillus clavatus, using broth microdilution (MIC) method (CLSI guidelines). Among them, some compounds exhibited promising antibacterial activity against the tested strains. All synthesized compounds were characterized by IR,1H-NMR, mass, and elemental analysis.

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

“…Gadhave and colleagues [24] synthesized multi-fluorinated pyrazole-pyrazolone and chromone-pyrazolone compounds 21, 22, 23 and 24 ( Fig. 3) which exerted favorable antibacterial effects (Table 1), whereas all the compounds exhibited poor antifungal activity profile.…”

Synthesis and Antibacterial Screening of Novel Fluorine Containing Heterocycles

“…Flavones are known for their antimicrobial 23 , antiviral 24 , anticancer 25 and antiinflammatory 26 properties. Literature data also revealed that chromones substituted with pyrazole nucleus exhibit antimicrobial 27,28 activities.…”

Use of Ultrasound in the Synthesis of Heterocycles of Medicinal Interest

“…Gadhave et al [67] synthesized a series of novel fluorine-containing chromone-pyrazolone (64) and pyrazolepyrazolone (65) from multifluorinated pyrazolone by the Knoevenagel condensation reaction, used for the synthesis of diverse pharmaceutical products. All compounds were synthesized by conventional heating as well as ultrasound irradiation technique (Scheme 16).…”