Abstract
New N-adamantyl-2-amino-acylamides(3a–3f) and N-adamantyl-2-phenoxy-acetamides(6a–6d) were designed and synthesized by the modification of the amino group of amantadine 1 and the structures were confirmed by mass spectra(MS) and 1H NMR spectra. The antiviral potencies of the synthesized compounds were evaluated against the replication of influenza virus A/H3N2 subtype in Madin-Darby canine kidney(MDCK) cells. Among the amantadine derivatives, compound 3a had the strongest antiviral potency and showed activity similar to that of amantadine. Interestingly, the bulky and extended lipophilic moieties on the α-position of the carbonyl group resulted in decreases in potency.
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References
Peng S. X., Progress in Medicinal Chemistry, Chemical Industry Press, Beijing, 2011, 150
Shigeta S., Mori S., Kodama E., Kodama J., Takahashi K., Yamase T., Antiviral Res., 2003, 58(3), 265
Liu J., Mei W. J., Li A. X., Tan C. P., Shi S., Ji L. N., Chem. J. Chinese Universities, 2004, 25(1), 1
Schnell J. R., Chou J. J., Nature, 2008, 451, 591
Stouffer A. L., Acharya R., Salom D., Levine A. S., Costanzo L. D., Soto C. S., Tereshko V., Nanda V., Stayrook S., de Grado W. F., Nature, 2008, 451, 596
Lipatov A. S., Govorkova E. A., Webby R. J., Ozaki H., Peiris M., Guan Y., Poon L., Webster R. G., J. Virol., 2004, 78, 8951
Kolocouris N., Foscolos G. B., Kolocouris A., Marakos P., Pouli N., Fytas G., Ikeda S., de Clercq E., J. Med. Chem., 1994, 37, 2896
Kolocouris A., Spearpoint P., Martin S. R., Hay A., López-Querol M., Sureda F. X., Padalko E., Neyts J., de Clercq E., Bioorg. Med. Chem. Lett., 2008, 18, 6156
Stamatiou G., Kolocouris A., Kolocouris N., Fytas G., Foscolos G. B., Neyts J., de Clercq E., Bioorg. Med. Chem. Lett., 2001, 11, 2137
Tataridis D., Fytas G., Kolocouris A., Fytas C., Kolocouris N., Foscolos G. B., Padalko E., Neyts J., de Clercq E., Bioorg. Med. Chem. Lett., 2007, 17, 692
Zoidis G., Tsotinis A., Kolocouris N., Kelly J. M., Prathalingam S. R., Naesens L., de Clercq E., Org. Biomol. Chem., 2008, 6, 3177
Zoidis G., Kolocouris N., Naesens L., de Clercq E., Bioorg. Med. Chem., 2009, 17, 1534
Xiu Y. J., Study on Syntheses of Natural Peptides Hirsutellide A and Tasiamide, Tianjin University, Tianjin, 2004
Zhao Y., Yao J. S., Dai G., Hu J. Q., J. Shandong Inst. Light Ind., 2009, 23(2), 6
Xie Y., Weng L. L., West Chin. J. Pharm. Sci., 2005, 20(4), 310
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Supported by the Scientific Research Foundation for PhD of Shenyang University of Chemical Technology, China (No.200807).
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Liu, D., Fan, Zc., Jiang, Jm. et al. Synthesis and antiviral activity of N-adamantyl-2-amino(or 2-phenoxy)-acylamides. Chem. Res. Chin. Univ. 29, 706–709 (2013). https://doi.org/10.1007/s40242-013-2380-8
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DOI: https://doi.org/10.1007/s40242-013-2380-8