Abstract
Synthesis of some new multi-functional analogues of 2′-hydroxy chalcone containing isoxazole and pyrazole functions were synthesized, and their pharmacological activity was tested. Chalcone derivatives were synthesized by the reaction of 2′-hydroxy acetophenone with various substituted benzaldehydes in a basic medium. Aurones were isolated upon treatment with mercuric acetate. Synthesized chalcones and aurones were converted into the corresponding isoxazole and pyrazole derivatives upon their reaction with hydroxylamine hydrochloride or hydrazine hydrate, respectively. Structures of the compounds were confirmed by spectroscopic methods. All synthesized compounds were tested for antioxidant and antibacterial potential. Some of those demonstrated excellent antioxidant activity, and one product was identified as a promising antimicrobial candidate.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Change history
12 September 2019
The fourth author of the article should read S. A. Ahmada<Superscript><Emphasis Type="Italic">a</Emphasis></Superscript>.
References
Rahman, A., Qureshi, R., Kiran, M., and Ansari, F.L., Turk. J. Chem., 2007, vol. 31, p. 25.
Dubey, R.K., Dixit, P., and Arya, S., Int. J. Innov. Res. Sci., Eng. Technol., 2014, vol. 3, no. 1, p. 8141.
Haudecoeur, R. and Boumendjel, A., Curr. Med. Chem., 2012, vol. 19, p. 2861. doi https://doi.org/10.2174/092986712800672085
Deepthi, M., Harinadha, B.V, and Madhava, R.B., Indian J. Chem., 2013, vol. 52, p. 1455.
Lee, C.Y., Chew, E.H., and Go, M.L., Eur. J. Med. Chem., 2010, vol. 45, no. 7, p. 2957. doi https://doi.org/10.1016/j.ejmech.2010.03.023.
Zheng, X., Wang H., Yun-Mei, L., Xu, Y., Min, T., Yu-Hong, W., and Duan-Fang, L., J. Heterocycl. Chem., 2015, vol. 52, p. 296. doi https://doi.org/10.1002/jhet.1969
Carrasco, M.P., Newton, A.S., Goncalves, L., Gois, A., Machado, M., Gut, J., Nogueira, F., Hanscheid, T., Guedes, R.C., Santos, D.J.V.A., Rosenthal, P.J., and Moreira, R., Eur. J. Med. Chem., 2014, vol. 80, p. 523. doi https://doi.org/10.1016/j.ejmech.2014.04.076.
Bandgar, B.P. and Patil, S.A., Eur. J. Med. Chem., 2010, vol. 45, p. 3223. doi https://doi.org/10.1016/j.ejmech.2010.03.045.
Shin, S.Y., Shin, M.C., Shin, J.S., Lee, K.T., and Lee, Y.S. Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 4520. doi https://doi.org/10.1016/j.bmcl.2011.05.117.
Detsi, A., Majdalani, M., Kontogiorgis, C.A., Hadjipavlou-Litina, D., and Kefalas, P., Bioorg. Med. Chem., 2009, vol. 17, p. 8073. doi https://doi.org/10.1016/j.bmc.2009.10.002
Zhuang, Y., Chen, L., Sun, L., and Cao, J., J. Funct. Foods, 2012, vol. 4, p. 331. doi https://doi.org/10.1016/j.jff.2012.01.001
Oyaizu, M., Jpn. J. Nutr. Diet., 1986, vol. 44, p. 307. doi https://doi.org/10.5264/eiyogakuzashi.44.307
Harrigan, F.W., Laboratory Methods in Food Microbiology, London: Academic Press, 1998, 3rd ed.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Irshad, M., Ali, Q., Iram, F. et al. Aurones and Analogues: Promising Heterocyclic Scaffolds for Development of Antioxidant and Antimicrobial Agents. Russ J Gen Chem 89, 1519–1527 (2019). https://doi.org/10.1134/S1070363219070235
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363219070235