Efficient One-Pot Synthesis of Pyrazole–Pyrazol-3-one Hybrid Analogs and Evaluation of Their Antimicrobial Activity

• Published in: Russian journal of organic chemistry Vol. 58; no. 1; pp. 81 - 86
• Main Authors: Sivaganesh, T., Padmaja, P., Reddy, P. N.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 2022; Springer Nature; Springer Nature B.V
• Subjects: Antiinfectives and antibacterials; Antimicrobial agents; Aromatic compounds; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Hydrazines; Ions; Mass spectra; Molecular docking; NMR; Nuclear magnetic resonance; Organic Chemistry; Physical Sciences; Pyrazole; Science & Technology; Sodium acetate; chalcone; pyrazoline; antimicrobial activity; molecular docking study; one-pot synthesis; Pyrazole; PYRAZOLINES
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428022010110

An efficient one-pot protocol has been developed for the synthesis of 4-[(3-aryl-1-phenyl-1 H -pyrazol-4-yl)methylidene]-2,4-dihydro-3 H -pyrazol-3-ones by condensation of 3-aryl-1-phenyl-1 H -pyrazole-4-carbaldehydes, ethyl acetoacetate, and hydrazine hydrate using sodium acetate as catalyst. The synthesized compounds were characterized by spectral data (IR, 1 H and 13 C NMR, and mass spectra) and elemental analyses and tested for their in vitro antimicrobial activity against four bacterial and two fungal pathogens. The results of antimicrobial evaluation showed moderate to good inhibitory activity against all tested organisms and were further supported by the molecular docking study.