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Synthesis of Novel 1,2,3-Triazole Derivatives of Tolbutamide and Evaluation of Their Antibacterial, Antioxidant, and DPP-4 Inhibitory Activity

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Abstract

A series of new 1,2,3-triazole derivatives of tolbutamide analogues have been synthesized in a simple and effective way in high yields to explore the possibilities of some altered biological actions such as antibacterial, antioxidant and DPP-4 activities. Structure of the newly synthesized compounds is well characterized by various spectroscopic methods. Among all the synthesized compounds N-({[1-((2-fluoroethyl)sulfonyl)-1H-1,2,3-triazol-4-yl]methyl}carbamoyl)-4-methylbenzenesulfonamide and N-({[1-((4-chlorophenyl)-sulfonyl)-1H-1,2,3-triazol-4-yl]methyl}carbamoyl)-4-methylbenzenesulfonamide shows potent antibacterial and antioxidant activity as compared to standard drugs. Compound N-({[1-((4-chlorophenyl) sulfonyl)-1H-1,2,3-triazol-4-yl]methyl}carbamoyl)-4-methylbenzenesulfonamide has shown good DPP-4 inhibitory activity. Molecular docking and ADME studies have also been conducted to complement the experimental results.

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REFERENCES

  1. Chen, X., Hussain, S., Parveen, S., Zhang, S., Yang, Y., and Zhu, C., Curr. Med. Chem., 2012, vol. 19, pp. 3578–3604. https://doi.org/10.2174/092986712801323225

    Article  CAS  Google Scholar 

  2. de Ventura, T. and Zanitaro, V., Eur. J. Org. Chem., 2021, pp. 1201–1214. https://doi.org/10.1002/ejoc.202001437

  3. Agalave, S.G., Maujan, S.R., and Pore, V.S., Chem. Asian J., 2011, vol. 6, pp. 2696–2718. https://doi.org/10.1002/asia.201100432

    Article  CAS  Google Scholar 

  4. Narsimha, S., Satheesh Kumar, N., Kumara Swamy, R., Vasudeva Reddy, N., Althaf Hussain, S.K., and Srinivasa Rao, M., Bioorg. Med. Chem. Lett., 2016, vol. 26, pp. 1639–1644. https://doi.org/10.1016/j.bmcl.2016.01.055

    Article  CAS  Google Scholar 

  5. Kumara Swamy, B., Narsimha, S., Ranjith Kumar, T., Yellu Narsimha, R., and Vasudeva Reddy, N., Chem. Select., 2017, vol. 2 (29), pp. 9595–9598. https://doi.org/10.1002/slct.201701902

    Article  CAS  Google Scholar 

  6. Ramya Sucharitha, E., Satheesh Kumar, N., Manchal, R., Vasudeva Reddy, N., and Narsimha, S., Russ. J. Bioorg. Chem., 2021, vol. 47, pp. 896–905. https://doi.org/10.1134/S1068162021040208

    Article  Google Scholar 

  7. Sreerama, R., Manoj Kumar, N., Kumar Nukala, S., Ramya Sucharitha, E., Ramesh Babu, H., and Narsimha, S., Russ. J. Gen. Chem., 2021, vol. 91 (12), pp. 2515–2521. https://doi.org/10.1134/S1070363221120227

    Article  CAS  Google Scholar 

  8. Vasudeva Reddy, N., Narsimha, S., Kumara Swamy, B., Sudhakar, L., and Ranjith Kumar, T., Org. Commun., 2016, vol. 9, pp. 32–41.

    Google Scholar 

  9. Narsimha, S., Kumar Nukala, S., Savitha Jyostna, T., Manchal, R., Srinivasa Rao, M., and Vasudeva Reddy, N., J. Heterocyclic. Chem., 2020, vol. 57 (4), pp. 1655–1665. https://doi.org/10.1002/jhet.3890

    Article  CAS  Google Scholar 

  10. Ramya Sucharitha, E., Murali Krishna, T., Manchal, R., Ramesh, G., and Narsimha, S., Bioorg. Med. Chem. Lett., 2021, vol. 47, p. 128201. https://doi.org/10.1016/j.bmcl.2021.128201

    Article  CAS  Google Scholar 

  11. Rakesh, S., Narasimha, S. T., Manchal, R., Vasudeva Reddy, N., and Narsimha, S., Phosphorus Sulfur Silicon Relat. Elem., 2021, vol. 196, pp. 455–460. https://doi.org/10.1080/10426507.2020.1854257

    Article  CAS  Google Scholar 

  12. Pawełczyk, A., Sowa-Kasprzak, K., Olender, D., and Zaprutko, L., Int. J. Mol. Sci., 2018, vol. 19 (4), p. 1104. https://doi.org/10.3390/ijms19041104

    Article  CAS  Google Scholar 

  13. Janaki, R.D.B., Hari, B. P., Venkateswarlu, N., Vijaya, T., Rasheed, S., Naga, R.C., and Venkata, C.P., Indian J. Chem., 2018, vol. 57B, pp. 127–135.

    Google Scholar 

  14. Narsimha, S., Kumara Swamy, B., and Vasudeva Reddy, N., Syn. Commun., 2018, vol. 48, pp. 1220–1226. https://doi.org/10.1080/00397911.2018.1440315

    Article  CAS  Google Scholar 

  15. Narsimha, S., Kumara Swamy, B., Manchal, R., Reddy, Y.N., and Vasudeva Reddy, N., J. Chem. Sci., 2020, vol. 132, p. 59. https://doi.org/10.1007/s12039-020-1760-0

    Article  CAS  Google Scholar 

  16. Herries, D.G., Biochem. Educ., 1985, vol. 13, p. 146. https://doi.org/10.1016/0307-4412(85)90213-4

    Article  Google Scholar 

  17. Qiu, X., Janson, C.A., Smith, W.W., Green, S.M., McDevitt, P., Johanson, K., Carter, P., Hibbs, M., Lewis, C., Chalker, A., Fosberry, A., Lalonde, J., Berge, J., Brown, P., Houge-Frydrych, C.S., and Jarvest, R.L., Protein Sci., 2001, vol. 10, pp. 2008–2016. https://doi.org/10.1110/ps.18001

    Article  CAS  Google Scholar 

  18. Pires, D.E.V., Blundell, T.L., and Ascher, D.B., J. Med. Chem., 2015, vol. 58 (9), pp. 4066–4072. https://doi.org/10.1021/acs.jmedchem.5b00104

    Article  CAS  Google Scholar 

  19. Daina, A., Michielin, O., and Zoete, V., Sci. Rep., 2017, vol.7, pp. 42717. https://doi.org/10.1038/srep42717

    Article  Google Scholar 

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ACKNOWLEDGMENTS

The authors are thankful to the head, Department of Biotechnology, Chaitanya deemed to be University, Warangal, for providing data of biological activity.

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Authors and Affiliations

  1. Department of Chemistry, Chaitanya Deemed to be University, 506001, Warangal, Telangana, India

    Swathi Chirra, Sirassu Narsimha, Satheesh Kumar Nukala & Ravinder Manchal

  2. Department of Chemistry, Nalla Narasimha Reddy Education Society’s Group of Institutions, Integrated Campus (A), Narapally, 500088, Hyderabad, Telangana, India

    Swathi Chirra & Bhaskar Pittala

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  1. Swathi Chirra
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  2. Sirassu Narsimha
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  3. Satheesh Kumar Nukala
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Correspondence to Ravinder Manchal.

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This article does not contain any studies involving animals or human participants performed by any of the authors.

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Swathi Chirra, Narsimha, S., Nukala, S.K. et al. Synthesis of Novel 1,2,3-Triazole Derivatives of Tolbutamide and Evaluation of Their Antibacterial, Antioxidant, and DPP-4 Inhibitory Activity. Russ J Bioorg Chem 48, 1314–1321 (2022). https://doi.org/10.1134/S1068162022060097

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