Skip to main content
Log in

Nano Au/TiO2 Catalyzed Click Synthesis of Novel 1,2,3-Triazoles from S-Propargyl-1,2,4-triazole: Antibacterial Activity, Toxicity, and Docking Analysis

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A new series of 1,2,3-triazoles was synthesized by a titania-supported nano gold nanoparticles catalyzed 1,3-dipolar cycloaddition of aromatic azides with a 3-substituted 1,2,4-triazole terminal alkyne. The compounds were tested for antibacterial activity and antiradical efficiency. Further, in silico molecular docking studies were carried out against glucosamine-6-phosphate syntheses (PDB code: 2VF5) protein receptors. Toxicity of the compounds was studied through survival and climbing assays using an in vivo genetic model, Drosophila melanogaster.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme
Scheme
Scheme
Fig. 1.
Fig. 2.

REFERENCES

  1. Kiran, K., Ashok, D., Rao, B.A., Sarasija, M., and Rao, A.S., Russ. J. Gen. Chem., 2017, vol. 87, no. 6, p. 1288. https://doi.org/10.1134/S1070363217060251

    Article  CAS  Google Scholar 

  2. El-Sayed, W.A., Khalaf, H.S., Mohamed, S.F., Hussien, H., Kutkat, O.M., and Amar, A.E., Russ. J. Gen. Chem., 2017, vol. 87, no. 10, p. 2444. https://doi.org/10.1134/S1070363217100279

    Article  CAS  Google Scholar 

  3. Lakkakula, R., Roy, A., Mukkanti, K., and Sridhar, G., Russ. J. Gen. Chem., 2019, vol. 89, p. 831. https://doi.org/10.1134/S1070363219040315

    Article  CAS  Google Scholar 

  4. Prima, D.O., Vorontsova, E.V., Makarov, A.G., Makarov, A.Y., Bagryanskaya, I.Y., Mikhailovskaya, T.F., Slizhov, Y.G., and Zibarev, A.V., Mendeleev Commun., 2017, vol. 27, no. 5, p. 439. https://doi.org/10.1016/j.mencom.2017.09.002

    Article  CAS  Google Scholar 

  5. Meldal, M., and Tornoe, C.W., Chem. Rev., 2008, vol. 108, p. 2952. https://doi.org/10.1021/cr0783474

    Article  CAS  PubMed  Google Scholar 

  6. John, J., Thomas, J., and Dehaen, W., Chem. Commun., 2015, vol. 15, p. 10797. https://doi.org/10.1039/C5CC02319J

    Article  CAS  Google Scholar 

  7. Boominathan, M., Pugazhenthiran, N., Nagaraj, M., Muthusubramanian, S., Murugesan, S., and Bhuvanesh, N., ACS Sustain. Chem. Eng., 2013, vol. 1, p. 1405. https://doi.org/10.1021/sc400147r

    Article  CAS  Google Scholar 

  8. Fokin, V., Jia, G., and Sharpless, K.B., Patent US 8372986, 2013.

  9. James, S.O., Valery, V.F., Satoshi, U., and Tohru, F., Org. Synth., 2014, vol. 90, p. 96. https://doi.org/10.1002/0471264229.os090.09

    Article  Google Scholar 

  10. Wang, D., Salmon, L., Ruiz, J., and Astruc, J.D., Chem. Commun., 2013, vol. 49, p. 6956. https://doi.org/10.1039/C3CC43048K

    Article  CAS  Google Scholar 

  11. Wang, Y., Xie, Y., Qu, H., Wang, H., Pan, Y., and Huang, F., J. Org. Chem., 2014, vol. 79, p. 4463. https://doi.org/10.1021/jo5004339

    Article  CAS  PubMed  Google Scholar 

  12. Astruc, D., Lu, F., and Aranzaes, J.R., Angew. Chem. Int. Ed., 2005, vol. 44, p. 7852. https://doi.org/10.1002/anie.200500766

    Article  CAS  Google Scholar 

  13. Haruta, M., Kobayashi, T., Sano, H., and Yamada, N., Chem. Lett., 1987, vol. 2, p. 405. https://doi.org/10.1246/cl.1987.405

    Article  Google Scholar 

  14. Fan, L., Ichikuni, N., Shimazu, S., and Uematsu, T., Appl. Catal. (A), 2003, vol. 246, p. 87. https://doi.org/10.1016/S0926-860X(03)00002-4

    Article  CAS  Google Scholar 

  15. Subramanian, V., Wolf, E.E., and Kamat, P.V., J. Am. Chem. Soc., 2004, vol. 126, p. 4943. https://doi.org/10.1021/ja0315199

    Article  CAS  PubMed  Google Scholar 

  16. Centeno, M. A., Portales, C., Carrizosa, I., and Odriozola, J.A., Cat. Lett., 2005, vol. 102, p. 289. https://doi.org/10.3390/catal6100158

    Article  CAS  Google Scholar 

  17. Vishwanath, T., Kalluraya, B., Hemanth, K., and Revanasiddappa, B.C., Russ. J. Gen. Chem., 2020, vol. 90, no. 1, p. 142. https://doi.org/10.1134/S1070363220010223

    Article  Google Scholar 

  18. Raghu, S.V., Mohammad, F., Chua, J.Y., Lam, J.S.W., Loberas, M., Sahani, M., Claridge-Chang, A., Mol. Brain., 2018, vol. 11, no. 1, p. 46. https://doi.org/10.1186/s13041-018-0390-7

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Fun, H., Kia, R., Jebas, S.R., Sujith, K.V., and Kalluraya, B., Acta Crystallogr. (E), 2009, vol. 65, p. 0618. https://doi.org/10.1107/S1600536809006527

    Article  CAS  Google Scholar 

  20. Pavia, D.L., Lampman, G.A., Kriz, G.A., and Vyvyan, J.R., Introduction to Spectroscopy, Boston: Thomson Learning, 2001, p. 143.

  21. Vishwanath, T., and Kalluraya, B., J. Phy. Org. Chem., 2019, article e4040. https://doi.org/10.1002/poc.4040

  22. Ansari, F. L., Nazir, S., Noureen, H., and B. Miraza, Chem. Biodivers., 2005, vol. 2, p. 1656. https://doi.org/10.1002/cbdv.200590135

    Article  CAS  PubMed  Google Scholar 

  23. Schrodinger Release 2019-2: Maestro, Schrödinger, LLC, New York, 2019.

  24. Mouilleron, S., Badet-Denisot, M.A., and GolinelliPimpaneau, B., J. Mol. Biol., 2008, vol. 377, no. 4, p. 1174. https://doi.org/10.1016/j.jmb.2008.01.077

    Article  CAS  PubMed  Google Scholar 

  25. Brand-Williams, W., Cuvelier, M.E., and Berset, C., LWT-Food Science and Technology, 1995, vol. 28, p. 25. https://doi.org/10.1016/S0023-6438(95)80008-5

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. Turukarabettu.

Ethics declarations

The authors declared no conflict of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Turukarabettu, V., Kalluraya, B., Kumar, P. et al. Nano Au/TiO2 Catalyzed Click Synthesis of Novel 1,2,3-Triazoles from S-Propargyl-1,2,4-triazole: Antibacterial Activity, Toxicity, and Docking Analysis. Russ J Gen Chem 93, 2638–2644 (2023). https://doi.org/10.1134/S1070363223100183

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363223100183

Keywords:

Navigation