Abstract
A novel series of 1,2,3-triazolyl isoxazole derivatives is synthesized from the corresponding propargylated isoxazoles and a number of aryl azides by the Click reaction. The highest yields of the reaction are achieved in the presence of copper sulphate pentahydrate and sodium ascorbate, and using DMF:water (2:1) as a medium. The compounds structures are elucidated from various spectral data. Antimicrobial activity tests of the title compounds demonstrate their moderate to good results compared to the standard.
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Daidone, G., Raffa, D., Maggio, B., Plescia, F., Cutuli, V.M.C., Mangano, N.G., and Caruso, A., Arch. Pharm. Pharm. Med. Chem., 1999, vol. 332, p. 50. doi https://doi.org/10.1002/(SICI)1521-4184(19993)332:2<50::AID-ARDP50>3.0.CO;2-S
Al-Tel, T.H., Al-Qawasmeh, R.A., and Zaarour, R., Eur. J. Med. Chem., 2011, vol. 46, p. 1874. doi https://doi.org/10.1016/j.ejmech.2011.02.051
Li, W., Hwang, D., Chen, D., Shen, C., Huang, C., Chen, T., Lin, C., Chang, Y., Lo, Y., Tseng, H., Lin, Lin, C., Song, J., Chen, H., Chen, S., Wu, S., and Chen, C., J. Med. Chem., 2003, vol. 46, p. 1706. doi https://doi.org/10.1021/jm020471r
Lang, S.A., Jr. and Lin, Y.I., Comprehensive Heterocyclic Chem., 1984, vol. 6, p. 1.
He, Y.W., Dong, C.Z., Zhao, J.Y., Ma, L.L., Li, Y.H., and Aisa, H.A., Eur. J. Med. Chem., 2014, vol. 76, p. 245. doi https://doi.org/10.1016/j.ejmech.2014.02.029
Ulloora, S., Shabaraya, R., and Adhikari, A.V., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 3368. doi https://doi.org/10.1016/j.bmcl.2013.03.086
Abuo Rahma, G.E.D.A.A., Abdel Aziz, M., Farag, N.A., and Kaoud, T.S., Eur. J. Med. Chem., 2014, vol. 83, p. 398. doi https://doi.org/10.1016/j.ejmech.2014.06.049
Wenjuan, Z., Zhi, Li., Meng, Z., Feng, Wu., Xueyan, Hou, Hao, Luo, Hao, Liu, Xuan Han, Guoyi Yan, Zhenyu Ding, and Rui Li, Bioorg. Med. Chem. Lett., 2014, vol. 24, no. 3, p. 799. doi https://doi.org/10.1016/j.bmcl.2013.12.095
Pervaram, S., Ashok, D., Rao, B.A., Sarasija, M., and Reddy, C.V.R., Russ. J. Gen. Chem., 2017, vol. 87, p. 2454. doi https://doi.org/10.1134/S1070363217100280
Sowjanya, T., Jayaprakash Rao, Y., and Murthy, N.Y.S., Russ. J. Gen. Chem., 2017, vol. 87, no. 8, p. 1864. doi https://doi.org/10.1134/S1070363217080357
Alcaide, B., Almendros, P., and Salgado N.R., Tetrahedron Lett., 2001, vol. 42, p. 1503. doi https://doi.org/10.1016/S0040-4039(00)02298-X
Santos Maria, M.M., Faria, Iley J., Coles S.J., Hursthouse, M.B., Martins M.L., and Moreira R., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 193. doi https://doi.org/10.1013/j.bmcl.2009.10.137
Gang Shen, Brian S.J., and Blagg Radester, Org. Lett., 2005, vol. 7(11),p. 2157. doi https://doi.org/10.1021/o1050580a
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Thotla, K., Giri Noole, V., Kedika, B. et al. An Efficient Synthesis and Antimicrobial Activity of 5-{2-[(1-Aryl-1H-1,2,3-triazol-4-yl)methoxy]-5-bromophenyl}isoxazoles. Russ J Gen Chem 89, 789–793 (2019). https://doi.org/10.1134/S1070363219040248
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DOI: https://doi.org/10.1134/S1070363219040248