Abstract
A series of bis-isoxazoles blended chalcones 7a–7j are synthesized in high yields. The combination of three pharmacologically active moieties in a single scaffold results in the synergistic effect in their bioactivity. All the newly synthesized compounds are characterized by IR, NMR and Mass spectroscopy. The target compounds 7a–7j are assessed for their antimicrobial activity and these demonstrate high to excellent activity against tested bacterial and fungal strains. The products 7f, 7h, 7j, and 7i demonstrate potent antimicrobial activity at concentrations 75 and 100 μg/mL.
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Baraldi, P., Barco, A., Benetti, S., Pollini, G., and Simoni, D., Synthesis, 1987, vol. 1987, no. 10, p. 857. doi 10.1093/jac/20.6.857
Verma, N., Kumar, S., and Ahmed, N., RSC Advances, 2016, vol. 6, no. 56, p. 51183. doi 10.1039/C6RA08710H
Niu, C., Yin, L., Nie, L.F., Dou, J., Zhao, J.Y., Li, G., and Aisa, H.A., Bioorganic Med. Chem., 2016, vol. 24, no. 21, p. 544. doi 10.1016/j.bmc.2016.08.066
da Silva, G.D., da Silva, M.G., Souza, E.M., Barison, A., Simões, S.C., Varotti, F.P., Barbosa, L.A., Viana, G.H., and Villar, J.A., Molecules, 2012, vol. 17, no. 9, p. 10331. doi 10.3390/molecules170910331
de Mello, T.F., Bitencourt, H.R., Pedroso, R.B., Aristides, S.M., Lonardoni, M.V., and Silveira, T.G., Exp. Parasitol., 2014, vol. 136, p. 27. doi 10.1016/j.exppara.2013.11.003
Liu, X.L., Xu, Y.J., and Go, M.L., Eur. J. Med. Chem., 2008, vol. 43, no. 8, p. 1681. doi 10.1016/j.ejmech.2007.10.007
Tsuchiya, H., Sato, M., Akagiri, M., Takagi, N., Tanaka, T., and Iinuma, M., Die Pharmazie, 1994, vol. 49, no. 10, p. 756.
Go, M., Wu, X., and Liu, X., Curr. Med. Chem., 2005, vol. 12, no. 4, p. 483. doi 10.2174/0929867053363153
Hans, R.H., Guantai, E.M., Lategan, C., Smith, P.J., Wan, B., Franzblau, S.G., Gut, J., Rosenthal, P.J., and Chibale, K., Bioorganic Med. Chem. Lett., 2010, vol. 20, no. 3, p. 94. doi 10.1016/j.bmcl.2009.12.062
Mishra, N., Arora, P., Kumar, B., Mishra, L.C., Bhattacharya, A., Awasthi, S.K., and Bhasin, V.K., Eur. J. Med. Chem., 2008, vol. 43, no. 7, p. 1530. doi 10.1016/j.ejmech.2007.09.014
Cheenpracha, S., Karalai, C., Ponglimanont, C., Subhadhirasakul, S., and Tewtrakul, S., Bioorganic Med. Chem., 2006, vol. 14, no. 6, p. 1710. doi 10.1016/j.bmc.2005.10.019
Chiaradia, L.D., Mascarello, A., Purificação, M., Vernal, J., Cordeiro, M.N.S., Zenteno, M.E., Villarino, A., Nunes, R.J., Yunes, R.A., and Terenzi, H., Bioorganic Med. Chem. Lett., 2008, vol. 18, no. 23, p. 622. doi 10.1016/j.bmcl.2008.09.105
Mukherjee, S., Kumar, V., Prasad, A.K., Raj, H.G., Bracke, M.E., Olsen, C E., Jain, S.C., and Parmar, V.S., Bioorganic Med. Chem., 2001, vol. 9, no. 2, p. 337. doi 10.1016/S0968-0896(00)00249-2
Padhye, S., Ahmad, A., Oswal, N., Dandawate, P., Rub, R.A., Deshpande, J., Swamy, K.V., and Sarkar, F.H., Bioorganic Med. Chem. Lett., 2010, vol. 20, no. 19, p. 5818. doi 10.1016/j.bmcl.2010.07.128
Vogel, S., Barbic, M., Juergenliemk, G., and Heilmann, J., Eur. J. Med. Chem., 2010, vol. 45, no. 6, p. 2206–2213. doi 10.1016/j.ejmech.2010.01.060
Satyanarayana, M., Tiwari, P., Tripathi, B.K., Srivastava, A., and Pratap, R., Bioorganic Med. Chem., 2004, vol. 12, no. 5, p. 883. doi 10.1016/j.bmc.2003.12.026
Bandgar, B.P., Gawande, S.S., Bodade, R.G., Totre, J.V., and Khobragade, C.N., Bioorganic Med. Chem., 2010, vol. 18, no. 3, p. 1364. doi 10.1016/j.bmc.2009.11.066
De Leon, E., Alcaraz, M., Dominguez, J., Charris, J., and Terencio, M., Inflamm. Res., 2003, vol. 52, no. 6, p. 246. doi 10.1007/s00011-003-1164-x
Zhao, L.-M., Jin, H.-S., Sun, L.-P., Piao, H.-R., and Quan, Z.-S., Bioorganic Med. Chem. Lett., 2005, vol. 15, no. 22, p. 5027. doi 10.1016/j.bmcl.2005.08.039
Sunitha, V., Kumar, A.K., Shankar, B., Kumar, A.A., Krishna, T., Lincoln, C.A., and Pochampalli, J., Russ. J. Gen. Chem., 2017, vol. 87, no. 2, p. 322. doi 10.1134/S1070363217020281
Bauer, A., Am. J. Clin. Pathol., 1966, vol. 45, p. 493. doi 10.1093/ajcp/45.4_ts.493
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Sunitha, V., Kumar, A.K., Mahesh, M. et al. Synthesis and Antimicrobial Evaluation of Bis-3,5-disubstituted Isoxazoles Based Chalcones. Russ J Gen Chem 88, 1904–1911 (2018). https://doi.org/10.1134/S1070363218090232
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DOI: https://doi.org/10.1134/S1070363218090232