Abstract
Three structural isomers of pyridyl-4-oxy-substituted N-hydroxy amides of cinnamic acid (PyOCHA) have been synthesized for the first time. The relationship between their antiviral activity against hepatitis C virus (HCV) and inhibition of histone deacetylases of different cellular localization has been studied.
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Peserico, A. and Simone, C., J. Biomed. Biotechnol., 2011, vol. 2011. doi doi 10.1155/2011/371832
Sadoul, K., Wang, J., Diagouraga, B., and Khochbin, S., J. Biomed. Biotechnol., 2011, vol. 2011. doi 10.1155/2011/970382
Lombardi, P.M., Cole, K.E., Daniel, P., Dowling, D.P., and Christianson, D.W., Curr. Opin. Struc. Biol., 2011, vol. 21, pp. 735–743.
Napper, A.D., Hixon, J., McDonagh, T., Keavey, K., Pons, J., Barker, J., Yau, W.T., Amouzegh, P., Flegg, A., Hamelin, E., Thomas, R.J., Kates, M., Jones, S., Navia, M.A., Saunders, J.O., DiStefano, P.S., and Curtis, R., J. Med. Chem., 2005, vol. 48, pp. 8045–8054.
Witt, O., Deubzer, H.E., Milde, T., and Oehme, I., Cancer Lett., 2009, vol. 277, pp. 8–21.
Lahm, A., Paolini, C., Pallaoro, M., Nardi, M.C., Jones, P., Neddermann, P., Sambucini, S., Bottomley, M.J., Lo, SurdoP., Carfı, A., Koch, U., De Francesco, R., Steinkuhler, C., and Gallinari, P., Proc. Natl. Acad. Sci. U. S. A., 2007, vol. 104, pp. 17335–17340.
Herbein, G. and Wendling, D., Clin. Epigenet., 2010, vol. 1, pp. 13–24.
Zhang, L., Ogden, A., Aneja, R., and Zhou, J., Pharmacol. Ther., 2016, vol. 164, pp. 120–125.
Miura, K., Taura, K., Kodama, Y., Schnabl, B., and Brenner, D.A., Hepatology, 2008, vol. 48, pp. 1420–1429.
Paris, M., Porcelloni, M., Binaschi, M., and Fattori, D., J. Med. Chem., 2008, vol. 51, pp. 1505–1529.
Chan, C.T., Qi, J., Smith, W., Paranol, R., Mazitschek, R., West, N., Reeves, R., Chiosis, G., Schreiber, S.L., Bradner, J.E., Paulmurugan, R., and Gambhir, S.S., Cancer Res., 2014, vol. 74, pp. 7475–7486.
Chakrabarti, A., Melesina, J., Kolbinger, F.R., Oehme, I., Senger, J., Witt, O., Sippl, W., and Jung, M., Future Med. Chem., 2016, vol. 8, pp. 1609–1634.
Ai, T., Xu, Y., Qiu, L., Geraghty, R.J., and Chen, L., J. Med. Chem., 2015, vol. 58, pp. 785–800.
Kozlov, M.V., Kleymenova, A.A., Konduktorov, K.A., Malikova, A.Z., Kamarova, K.A., Novikov, R.A., and Kochetkov, S.N., Russ. J. Bioorg. Chem., 2016, vol. 42, pp. 191–197.
Pietschmann, T., Lohmann, V., Kaul, A., Krieger, N., Rinck, G., Rutter, G., Strand, D., and Bartenschlager, R., J. Virol., 2002, vol. 76, pp. 4008–4021.
Ai, T., Qiu, L., Xie, J., Geraghty, R.J., and Chen, L., Bioorg. Med. Chem., 2016, vol. 24, pp. 686–692.
Wu, J., Zhang, D., and Wei, S., Synth. Commun., 2005, vol. 35, pp. 1213–1222.
Zhan, R. and Li, Y., Catalysts, 2017, vol. 7. doi 10.3390/catal7110337
Ujino, S., Yamaguchi, S., Shimotohno, K., and Takaku, H., J. Biol. Chem., 2009, vol. 284, pp. 6841–6846.
Imai, J., Maruya, M., Yashiroda, H., Yahara, I., and Tanaka, K., EMBO J., 2003, vol. 22, pp. 3557–3567.
Chen, J., Wu, X., Chen, S., Chen, S., Xiang, N., Chen, Y., and Guo, D., Biochem. Biophys. Res. Commun., 2016, vol. 470, pp. 697–703.
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Original Russian Text © M.V. Kozlov, A.Z. Malikova, K.A. Kamarova, K.A. Konduktorov, S.N. Kochetkov, 2018, published in Bioorganicheskaya Khimiya, 2018, Vol. 44, No. 4, pp. 449–456.
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Kozlov, M.V., Malikova, A.Z., Kamarova, K.A. et al. Synthesis of Pyridyl-4-Oxy-Substituted N-Hydroxy Amides of Cinnamic Acid as New Inhibitors of Histone Deacetylase Activity and Hepatitis C Virus Replication. Russ J Bioorg Chem 44, 453–460 (2018). https://doi.org/10.1134/S1068162018040118
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DOI: https://doi.org/10.1134/S1068162018040118