Abstract
A series of new (E)-1-{2-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones (3a–3i) has been synthesized via copper-catalyzed 1,3-dipolar azide-alkyne cycloaddition reaction (CuAAC) of benzyl azide with substituted (E)-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-1-[2-(prop-2-ynyloxy)phenyl]prop-2-en-1-ones (2a–2i). The synthesized compounds have been characterized by their IR, lH, 13C NMR spectra, and mass spectroscopy data. All the compounds have been screened for antimicrobial activity.
Similar content being viewed by others
References
Patel, V.M. and Desai, K.R., Arkivoc, 2004, vol. 1, p. 123. DOI: 10.3998/ark.5550190.0005.111.
Abunada, N.M., Hassaneen, H.M., Kandile, N.G., and Miqdad, O.A., Molecules. 2008, vol. 13, p. 1501. DOI: 10.3390/molecules13071501.
Elguero, J., in Comprehensive Heterocyclic Chemistry, Katritzky, A.R., Rees, C.W., and Scriven, E.F.V., Eds., Oxford: Pergamon, 1996, vol. 3. DOI: 10.1016/B978-008096518-5.00078-2.
Abu-Orabi, S.T., Alfah, M.A., Jibril, I., Marii, F.M., and Ali, A.A.S., J. Heterocycl. Chem., 1989, vol. 26, p. 1461. DOI: 10.1002/jhet.5570260541.
Bala, S., Gupta, R.P., Sachdeva, M.L., Singh, A., and Pujari, H.K., Indian J. Chem. B, 1978, vol. 16, p. 481.
Mohan, J., Indian J. Chem. B, 1983, vol. 22, p. 270.
Prasad, A., Ramalingam, R.J., Rao, A.B., Diwan P.V., and Sattur, P.B., Eur. J. Med. Chem., 1989, vol. 24, p. 199. DOI: 10.1016/0223-5234(89)90116-5.
Martin, G., German Patent, 2 240 043 (CI. C 07 d), March 1973, Chem. Abstr., 1973, vol. 78, p. 136302t.
Parmar, S.S., Rastogi, V.K., Agarwal, V.K., Sinha, J.N., and Chaudhari, A., Can. J. Pharm. Soc., 1974, vol. 9, p. 107.
George, T., Mehta, D.V., Tahilramani, R., Davvid J., and Talwalker, P.K., J. Med. Chem., 1971, vol. 14, p. 335. DOI: 10.1021/jm00286a016.
Genin, M.J., Allwine, D.A., Anderson, D.J., Barbachyn, M.R., Emmert, D.E., Garmon, S.A., Graber, D.R., Grega, K.C., Hester, J.B., Hutchinson, D.K., Morris, J., Reischer, R.J., Ford, C.W., Zurenco, G.E., Hamel, J.C., Schaadt, R.D., Stapert, D., and Yagi, B.H., J. Med. Chem., 2000, vol. 43, p. 953. DOI: 10.1021/jm990373e
Bochis, R.J., Chabala, J.C., Harris, E., Peterson, L.H., Barash, L., Beattie, T., Brown, J.E., Graham, D.W., Waksmunski, F.S., Tischler, M., Joshua, H., Smith, J., Colwell, L.F., Wyvratt, M.J.Jr., and Fisher, M.H., J. Med. Chem., 1991, vol. 34, p. 2843. DOI: 10.1021/jm00113a024.
Buckle, D.R., Outred, D.J., Rockell, C.J.M., Smith, H., and Spicer, B.A., J. Med. Chem., 1983, vol. 26, p. 251. DOI: 10.1021/jm00356a025
Buckle, D.R., Rockell, C.J.M., Smith, H., and Spicer, B.A., J. Med. Chem., 1986, vol. 29, p. 2262. DOI: 10.1021/jm00161a022.
Micetich, R.G., Maiti, S.N., Spevak, P., Hall, T.W., Yamabe, S., Ishida, N., Tanaka, M., Yamazaki, T., Nakai, A., and Ogawa, K., J. Med. Chem. 1987, vol. 30, p. 1469. DOI: 10.1021/jm00391a032.
Brockunier, L.L., Parmee, E.R., Ok, H.O., Candelore, M.R., Cascieri, M.A, Colwell, L.F., Deng, L., Feeney, W.P., Forrest, M.J., Hom, G.J., Macintyre, D.E., Tota, L., Wyvatt, M.J., Fisher, M.H., and Weber, A.E., Bioorg. Med. Chem. Lett., 2000, vol. 10, p. 2111. DOI: 10.1016/S0960-894X(00)00422-4.
Alvarez, R., Velazquez, S., San-Felix, A., Aquaro, S., Clercq, E.D., Perno, C.F., Karlesson, A., Balzarini, J., and Camarasa, M.J., J. Med. Chem. 1994, vol. 37, p. 4185. DOI: 10.1021/jm00050a015.
Olofson R.A. and Kendall, R.V., J. Org. Chem., 1970, vol. 35, p. 2246. DOI: 10.1021/jo00832a031.
Lid Storm, P., Tiernery, J., Wathey, B., and Westman, J., Tetrahedron, 2001, vol. 57, p. 9225. DOI: 10.1016/S0040-4020(01)00906-1.
Ashok, D., Mohan Gandhi, D., Srinivas, G., and Vikas Kumar, A., Med. Chem. Res., 2014, vol. 23, p. 3005. DOI: 10.1007/s00044-013-0880-1
Ashok, D., Hanumantha, R.V., and Sreenivas, P., Heterocyclic. Commun., 2013, vol. 19, p. 363. DOI: 10.1515/hc-2013-0046
Ashok, D., Sudershan, K., and Khalilullah, M., Green Chem. Lett. Rev., 2012, vol. 5, p. 121. DOI: 10.1080/17518253.2011.584912
Ashok, D. and Shravani, D., Tetrahedron Lett., 2008, vol. 49, p. 7227. DOI: 10.1016/j.tetlet.2008.10.016.
Wu, R.Y., Bot. Bull. Acad. Sin., 1984, vol. 25, p. 111.
Author information
Authors and Affiliations
Corresponding author
Additional information
The text was submitted by the authors in English.
Rights and permissions
About this article
Cite this article
Ashok, D., Padmavati, K. Microwave-assisted synthesis of 1-{2-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones and their antimicrobial activity. Russ J Gen Chem 86, 907–914 (2016). https://doi.org/10.1134/S1070363216040253
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363216040253