Synthesis, Characterization and Biological Evaluation of Novel 3-Methyl-5-pyrazolone Derivatives

Azim, Fazli; Nadeem, Humaira; Imran, Muhammad; Naz, Shagufta; Haq, Ihsan-ul-; Muhammad, Nawshad; Hayat, Aneela; Islam, Md Shahidul

doi:10.26655/JMCHEMSCI.2021.1.6

Document Type : Original Article

Authors

¹ Department of Pharmaceutical Chemistry, Riphah Institute of Pharmaceutical Sciences, Riphah International University, Islamabad, Pakistan

² Department of Pharmacy, Quaid-e-Azam University, Islamabad

³ Interdisciplinary Research Centre in Biomedical Materials (IRCBM) COMSATS, Institute of Information Technology, Lahore

⁴ Department of Pathology, Bacha Khan Medical College, Mardan

⁵ Department of Tissue Engineering and Applied Cell Sciences, Tehran University of Medical Sciences, Iran

https://doi.org/10.26655/JMCHEMSCI.2021.1.6

Abstract

Recently, infectious diseases have increased enormously, causing a major threat to public health despite the marvelous progress in the medicinal chemistry. Fused pyrazole derivatives are having a wide range of pharmacological activities, playing a vital role as potential therapeutic agents in various pathological conditions. In the present study, novel fused pyrazoles derivatives were synthesized and evaluated for protein kinase inhibition, antioxidant, and antimicrobial activities. 3-Methyl-5-pyrazolone was first prepared by treating ethyl acetoacetate with hydrazine hydrate in absolute ethanol. Then it was treated with different aromatic aldehydes (benzaldehyde, salicylaldehyde, vanillin, 4-diamethylaminobanzaldehyde, and cinnamaldehyde) to form benzylidene derivatives of pyrazoles. These substituted pyrazoles were then treated with hydrazine and phenylhydrazine to produce fused pyrazole ring systems. The synthesized compounds were purified by recrystallization, and then characterized using the spectroscopic techniques. All the compounds exhibited moderate antibacterial activity. Antioxidant potential was determined by three methods and most of the compounds exhibited good antioxidant potential. Two compounds including, 5a and 5e demonstrated protein kinase inhibitory activity. The results indicated that, the fused pyrazoles ring systems possess prominent biological properties.

Graphical Abstract

Keywords

Main Subjects

Heterocyclic chemistry

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Journal of Medicinal and Chemical Sciences

Synthesis, Characterization and Biological Evaluation of Novel 3-Methyl-5-pyrazolone Derivatives

References

References

Volume 4, Issue 1
January 2021
Pages 42-52

Synthesis, Characterization and Biological Evaluation of Novel 3-Methyl-5-pyrazolone Derivatives

References

References

Volume 4, Issue 1January 2021Pages 42-52

Volume 4, Issue 1
January 2021
Pages 42-52