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Synthesis and Properties of Symmetrical Bis-ureas Containing a 4-(Trifluoromethoxy)phenyl Fragment

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Abstract

A series of N,N′-disubstituted bis-ureas containing a lipophilic 4-(trifluoromethoxy)phenyl fragment were synthesized in 58–80% yields by reaction of 4-(trifluoromethoxy)phenyl isocyanate with aliphatic diamines. The synthesized compounds are promising as inhibitors of human soluble epoxide hydrolase.

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REFERENCES

  1. Rose, T.E., Morisseau, C., Liu, J.Y., Inceoglu, B., Jones, P.D., Sanborn, J.R., and Hammock, B.D., J. Med. Chem., 2010, vol. 53, p. 7067. https://doi.org/10.1021/jm100691c

    Article  CAS  Google Scholar 

  2. Anandan, S.K., Webb, H.K., Chen, D., Wang, Y.X., Aavula, B.R., Cases, S., Cheng, Y., Do, Z.N., Mehra, U., Tran, V., Vincelette, J., Waszczuk, J., White, K., Wong, K.R., Zhang, L.N., Jones, P.D., Hammock, B.D., Patel, D.V., Whitcomb, R., MacIntyre, D.E., Sabry, J., and Gless, R., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 983. https://doi.org/10.1016/j.bmcl.2010.12.042

    Article  CAS  Google Scholar 

  3. Wagner, K.M., McReynolds, C.B., Schmidt, W.K., and Hammock, B.D., Pharmacol. Ther., 2017, vol. 180, p. 62. https://doi.org/10.1016/j.pharmthera.2017.06.006

    Article  CAS  Google Scholar 

  4. Hammock, B.D., McReynolds, C.B., Wagner, K., Buckpitt, A., Cortes-Puch, I., Croston, G., Lee, K.S.S., Yang, J., Schmidt, W.K., and Hwang, S.H., J. Med. Chem., 2021, vol. 64, p. 1856. https://doi.org/10.1021/acs.jmedchem.0c01886

    Article  CAS  Google Scholar 

  5. Quin, S., Robertson, L., McQuaker, S.J., Price, N.C., Brand, M.D., and Hartley, R.C., Tetrahedron, 2010, vol. 66, p. 2384. https://doi.org/10.1016/j.tet.2010.01.103

    Article  CAS  Google Scholar 

  6. Salgado, V.L. and Hayashi, J.H., Vet. Parasitol., 2007, vol. 150, p. 182. https://doi.org/10.1016/j.vetpar.2007.08.032

    Article  CAS  Google Scholar 

  7. von Stein, R.T. and Soderlund, D.M., Mol. Pharmacol., 2012, vol. 81, p. 366. https://doi.org/10.1124/mol.111.075283

    Article  CAS  Google Scholar 

  8. Garton, A.J., Crew, A.P.A., Franklin, M., Cooke, A.R., Wynne, G.M., Castaldo, L., Kahler, J., Winski, S.L., Franks, A., Brown, E.N., Bittner, M.A., Keily, J.F., Briner, P., Hidden, C., Srebernak, M.C., Pirrit, C., O’Connor, M., Chan, A., Vulevic, B., Henninger, D., Hart, K., Sennello, R., Li, A.H., Zhang, T., Richard­son, F., Emerson, D.L., Castelhano, A.L., Arnold, L.D., and Gibson, N.W., Cancer Res., 2006, vol. 66, p. 1015. https://doi.org/10.1158/0008-5472.CAN-05-2873

    Article  CAS  Google Scholar 

  9. Burmistrov, V., Morisseau, C., Lee, K.S.S., Shiha­dih, D.S., Harris, T.R., Butov, G.M., and Ham­mock, B.D., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 2193. https://doi.org/10.1016/j.bmcl.2014.03.016

    Article  CAS  Google Scholar 

  10. Kodra, J.T., Jørgensen, A.S., Andersen, B., Behrens, C., Brand, C.L., Christensen, I.T., Guldbrandt, M., Jeppesen, C.B., Knudsen, L.B., Madsen, P., Nishi­mura, E., Sams, C., Sidelmann, U.G., Pedersen, R.A., Lynn, F.C., and Lau, J., J. Med. Chem., 2008, vol. 51, p. 5387. https://doi.org/10.1021/jm7015599

    Article  CAS  Google Scholar 

  11. Zhao, Y.F., Liu, Z.J., Zhai, X., Ge, D.D., Huang, Q., and Gong, P., Chin. Chem. Lett., 2013, vol. 24, p. 386. https://doi.org/10.1016/j.cclet.2013.02.004

    Article  CAS  Google Scholar 

  12. Liao, C., Liu, Y., Liu, C., Zhou, J., Li, H., Wang, N., Li, J., Liu, T., Ghaleb, H., Huang, W., and Qian, H., Bioorg. Med. Chem., 2018, vol. 26, p. 845. https://doi.org/10.1016/j.bmc.2017.12.048

    Article  CAS  Google Scholar 

  13. Della Ca’, N., Bottarelli, P., Dibenedetto, A., Aresta, M., Gabriele, B., Salerno, G., and Costa, M., J. Catal., 2011, vol. 282, p. 120. https://doi.org/10.1016/j.jcat.2011.06.003

    Article  CAS  Google Scholar 

  14. Linclau, B., Sing, A.K., and Curran, D.P., J. Org. Chem., 1999, vol. 64, p. 2835. https://doi.org/10.1021/jo9823442

    Article  CAS  Google Scholar 

  15. Wang, M., Han, J., Si, X., Hu, Y., Zhu, J., and Sun, X., Tetrahedron Lett., 2018, vol. 59, p. 1614. https://doi.org/10.1016/j.tetlet.2017.11.030

    Article  CAS  Google Scholar 

  16. Danilov, D.V., D’yachenko, V.S., Burmistrov, V.V., Butov, G.M., and Novakov, I.A., Russ. Chem. Bull., Int. Ed., 2022, vol. 71, p. 107. https://doi.org/10.1007/s11172-022-3383-8

    Article  CAS  Google Scholar 

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Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-73-10002).

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Correspondence to G. M. Butov.

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The authors declare the absence of conflict of interest.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 10, pp. 1096–1102 https://doi.org/10.31857/S051474922210007X.

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Kuznetsov, Y.P., Burmistrov, V.V. & Butov, G.M. Synthesis and Properties of Symmetrical Bis-ureas Containing a 4-(Trifluoromethoxy)phenyl Fragment. Russ J Org Chem 58, 1429–1433 (2022). https://doi.org/10.1134/S1070428022100074

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