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Catalyst-Free, One-Pot, Three-Component Synthesis of 5-Amino-1,3-diphenyl-1H-pyrazole-4-carbonitriles in Green Media, and Evaluation of Their Biological Activities

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Abstract

Objective: The tandem Knoevenagel-cyclocondensation reaction of aromatic aldehydes, malonitrile, and phenylhydrazine in water and ethanol at room temperature is described as an effective, one-pot, threecomponent synthesis of many scientifically relevant heterocyclic compounds. Methods: As a part of our efforts, we have synthesized pyrazole-4-carbonitriles and characterized using various spectroscopic methods and subjected for antimicrobial analysis. Results and Discussion: From our analysis, we observed best in vitro candidate as 5-amino-3-(2,5-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbonitrile. The molecular docking analysis on common bacterial target suggested the involvement of 2,2-dialkylglycine decarboxylase (PDB ID: 1D7U) as a target for compound (IVi) (docking score: –9.32 kcal/mol). Furthermore, a molecular dynamic simulation of 100 ns resulted in the stability of best docked candidate, (IVi): 1D7U. Conclusions: We propose that best docked candidate, (IVi) as potential antimicrobial agents.

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DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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ACKNOWLEDGMENTS

The authors are grateful to the Principal and Head, CS’s S.S. and L.S. Patkar College of Arts and Science, and V.P. Varde College of Commerce and Economics, Goregaon, Mumbai, 400104 India for his constant encouragement.

The author SM is thankful to Department of Pharmaceutical Sciences and Technology, Birla Institute of Technology, Mesra for usage of facility of Schrodinger Drug Discovery module, 2023.

Funding

This work was supported by regular institutional funding, and no additional grants were obtained.

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Authors and Affiliations

  1. Department of Chemistry, CS’s S.S. and L.S. Patkar College of Arts and Science, V. P. Varde College of Commerce and Economics, Goregaon, 400104, Mumbai, India

    N. N. Jha & R. S. Yamgar

  2. Department of Chemistry, Government College of Arts and Science, Aurangabad, 431001, Maharashtra, India

    B. R. Thorat

  3. Department of Pharmaceutical Sciences and Technology, Birla Institute of Technology, 835215, Mesra, India

    S. Yadav & S. N. Mali

  4. Department of Zoology, CS’s S.S. and L.S. Patkar College of Arts and Science, V. P. Varde College of Commerce and Economics, Goregaon, 400104, Mumbai, India

    S. A. Tawade

  5. School of Pharmacy, D.Y. Patil University (Deemed to be University), Sector 7, Nerul, 400706, Navi Mumbai, India

    S. N. Mali

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Contributions

The authors NJ, BT, SY, ST, and RY—selected the literature data on the research topic. The authors SM, NJ, and BT—contributed to manuscript preparation.

All authors participated in the discussions.

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Correspondence to S. N. Mali or R. S. Yamgar.

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Jha, N.N., Thorat, B.R., Yadav, S. et al. Catalyst-Free, One-Pot, Three-Component Synthesis of 5-Amino-1,3-diphenyl-1H-pyrazole-4-carbonitriles in Green Media, and Evaluation of Their Biological Activities. Russ J Bioorg Chem 50, 949–961 (2024). https://doi.org/10.1134/S1068162024030208

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