Synthesis and Antibacterial Activity of 4,4’-(Arylmethylene)Bis(3-Methyl-1- Phenyl-1H-Pyrazol-5-Ol) Derivatives in Presence Ce(SO4)2.4H2O as a Catalyst Under Solvent free Condition using Ultrasonication Technique

February 14, 2020


Mixture of aromatic aldehyde(1 mmol) and 1-phenyl-3-methyl-5-pyrazolone (2 mmol) in H2O–EtOH (1:1, 5 mL) at heating condition, was stirred thoroughly in the presence of a catalytic amount of Ce(SO4)2.4H2O (10 mg, 2.5 mol%) to afford 4,4’-(arylmethylene)bis(3-methyl-1-phenyl-pyrazol-5-ols) in excellent yields.

The synthesized derivatives were subjected for anti-bacterial activity using ciprofloxacin as standard drug against S. aureus and Pseudomonas aeruginosa using agar cup plate method. All the derivatives showed good antibacterial activity. The salient features of this method include simple procedure, mild conditions, easy purification, moderate to good yields of products and high generality.


4,4’-(arylmethylene)bis(3-methyl-1- phenyl-1H-pyrazol-5-ol) derivatives, ultrasonication technique


Han, Y. T.; Kim, K.; Choi, G.-I.; An, H.; Son, D.; Kim, H.; Ha, H.-J.; Son, J.-H.; Chung, S.-J.; Park, H.-J.; et al. Pyrazole-5-Carboxamides, Novel Inhibitors of Receptor for Advanced Glycation End Products (RAGE). Eur. J. Med. Chem. 2014, 79, 128–142.

Khillare, L.; Bhosle, M.; Bhalerao, M.; Kharat, K.; Mane, R. Synthesis of New Thiazolyl Coupled Pyrazoles Bearing 2,4-Thiazolidinedionyl Pharmacophore and Their Anti-Inflammatory and Antibacterial Evaluation. Antiinflamm. Antiallergy. Agents Med. Chem. 2017, 16 (1), 46–57.

Ramirez-Prada, J.; Robledo, S. M.; Velez, I. D.; Crespo, M. D. P.; Quiroga, J.; Abonia, R.; Montoya, A.; Svetaz, L.; Zacchino, S.; Insuasty, B. Synthesis of Novel Quinoline-Based 4,5-Dihydro-1H-Pyrazoles as Potential Anticancer, Antifungal, Antibacterial and Antiprotozoal Agents. Eur. J. Med. Chem. 2017, 131, 237–254.

Abdel-Mohsen, S. A.; El-Emary, T. I.; El-Kashef, H. S. Synthesis, Anti-Inflammatory and Antibacterial Activities of Novel Pyrazolo[4,3-g]Pteridines. Chem. Pharm. Bull. (Tokyo). 2016, 64 (5), 476–482.

Fonseca, D.; Leal-Pinto, S. M.; Roa-Cordero, M. V; Vargas, J. D.; Moreno-Moreno, E. M.; Macias, M. A.; Suescun, L.; Munoz-Castro, A.; Hurtado, J. J. Inhibition of C. Albicans Dimorphic Switch by Cobalt(II) Complexes with Ligands Derived from Pyrazoles and Dinitrobenzoate: Synthesis, Characterization and Biological Activity. Int. J. Mol. Sci. 2019, 20 (13).

Zhang, A.; Yang, Y.; Yue, Y.; Tao, K.; Hou, T.; Jin, H. N-[2-[(3-Chlorophenyl)Amino]-Phenyl]-3-(Difluoromethyl)-1-Methyl-1H-Pyrazole-4-ca Rboxamide: Synthesis, Crystal Structure, Molecular Docking and Biological Activities. Chem. Biodivers. 2019, 16 (7), e1900118.

Saleh, N. M.; El-Gazzar, M. G.; Aly, H. M.; Othman, R. A. Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors. Front. Chem. 2019, 7, 917.

OWEN, J. E. J.; SWANSON, E. E.; MEYERS, D. B. Anticonvulsant Activity of Pyrazole and of Pyrazole with Aliphatic Substitutions at the Three Position. J. Am. Pharm. Assoc. Am. Pharm. Assoc. (Baltim). 1958, 47 (1), 70–72.

Saueressig, S.; Tessmann, J.; Mastelari, R.; da Silva, L. P.; Buss, J.; Segatto, N. V.; Begnini, K. R.; Pacheco, B.; de Pereira, C. M. P.; Collares, T.; et al. Synergistic Effect of Pyrazoles Derivatives and Doxorubicin in Claudin-Low Breast Cancer Subtype. Biomed. Pharmacother. 2018, 98, 390–398.

Fatahala, S. S.; Nofal, S.; Mahmoud, E.; Abd El-Hameed, R. H. Pyrrolopyrazoles: Synthesis, Evaluation and Pharmacological Screening as Antidepressant Agents. Med. Chem. 2019, 15 (8), 911–922.

Raut, D. G.; Patil, S. B.; Kadu, V. D.; Hublikar, M. G.; Bhosale, R. B. Synthesis of Asymmetric 1-Thiocarbamoyl Pyrazoles as Potent Anti- Colon Cancer, Antioxidant and Anti-Inflammatory Agent. Anticancer. Agents Med. Chem. 2018, 18 (15), 2117–2123.

Pogaku, V.; Krishna, V. S.; Sriram, D.; Rangan, K.; Basavoju, S. Ultrasonication-Ionic Liquid Synergy for the Synthesis of New Potent Anti-Tuberculosis 1,2,4-Triazol-1-Yl-Pyrazole Based Spirooxindolopyrrolizidines. Bioorg. Med. Chem. Lett. 2019, 29 (13), 1682–1687.

Silva, V. L. M.; Elguero, J.; Silva, A. M. S. Current Progress on Antioxidants Incorporating the Pyrazole Core. Eur. J. Med. Chem. 2018, 156, 394–429.

Ganguly, S.; Jacob, S. K. Therapeutic Outlook of Pyrazole Analogs: A Mini Review. Mini Rev. Med. Chem. 2017, 17 (11), 959–983.

Author Details

Rajiv V Khobare

Ramkrushna P Pawar

Khandu D Warad

Amit P Tayde

Chandrakant B. Mane