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.
REFERENCES
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
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
Lakkakula, R., Roy, A., Mukkanti, K., and Sridhar, G., Russ. J. Gen. Chem., 2019, vol. 89, p. 831. https://doi.org/10.1134/S1070363219040315
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
Meldal, M., and Tornoe, C.W., Chem. Rev., 2008, vol. 108, p. 2952. https://doi.org/10.1021/cr0783474
John, J., Thomas, J., and Dehaen, W., Chem. Commun., 2015, vol. 15, p. 10797. https://doi.org/10.1039/C5CC02319J
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
Fokin, V., Jia, G., and Sharpless, K.B., Patent US 8372986, 2013.
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
Wang, D., Salmon, L., Ruiz, J., and Astruc, J.D., Chem. Commun., 2013, vol. 49, p. 6956. https://doi.org/10.1039/C3CC43048K
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
Astruc, D., Lu, F., and Aranzaes, J.R., Angew. Chem. Int. Ed., 2005, vol. 44, p. 7852. https://doi.org/10.1002/anie.200500766
Haruta, M., Kobayashi, T., Sano, H., and Yamada, N., Chem. Lett., 1987, vol. 2, p. 405. https://doi.org/10.1246/cl.1987.405
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
Subramanian, V., Wolf, E.E., and Kamat, P.V., J. Am. Chem. Soc., 2004, vol. 126, p. 4943. https://doi.org/10.1021/ja0315199
Centeno, M. A., Portales, C., Carrizosa, I., and Odriozola, J.A., Cat. Lett., 2005, vol. 102, p. 289. https://doi.org/10.3390/catal6100158
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
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
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
Pavia, D.L., Lampman, G.A., Kriz, G.A., and Vyvyan, J.R., Introduction to Spectroscopy, Boston: Thomson Learning, 2001, p. 143.
Vishwanath, T., and Kalluraya, B., J. Phy. Org. Chem., 2019, article e4040. https://doi.org/10.1002/poc.4040
Ansari, F. L., Nazir, S., Noureen, H., and B. Miraza, Chem. Biodivers., 2005, vol. 2, p. 1656. https://doi.org/10.1002/cbdv.200590135
Schrodinger Release 2019-2: Maestro, Schrödinger, LLC, New York, 2019.
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
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
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
Corresponding author
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
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363223100183