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Synthesis of N-Derivatives of Cytisine, Anabasine, and Salsoline Alkaloids with Pharmacophore 3-Aminopyridine-2(1H)-one and 5-Methyl-7-phenyloxazole[5,4-b]pyridine Cycles

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Abstract

The reaction of nucleophilic substitution of 2-chloro-N-(6-methyl-2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)acetamide and 2-(chloromethyl)-5-methyl-7-phenyloxazolo[5,4-b]pyridine with cytisine, anabasine, and salsoline alkaloids has afforded the corresponding derivatives. Structure of the obtained compounds has been confirmed by means of 1H and 13C NMR spectroscopy.

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References

  1. Soldatenkov, A.T., Kolyadina, N.M., and Shendrik, I.V., Osnovy organicheskoi khimii lekarstvennykh veshchestv (Fundamentals of Organic Chemistry of Medicinal Substances), Moscow: Khimiya, 2001.

    Google Scholar 

  2. Mashkovskii, M.D., Lekarstva XX veka (20th Century Medicine), Moscow: Novaya Volna, 1998.

    Google Scholar 

  3. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2007.

    Google Scholar 

  4. Mel’nikov, N.N., Pestitsidy. Khimiya, tekhnologiya i primenenie (Pesticides. Chemistry, Technology, and Application), Moscow: Khimiya, 1987.

    Google Scholar 

  5. Shimanskaya, M.V. and Leitis, L.Ya., Chem. Heterocycl. Compd., 1989, vol. 25, no. 5, p. 477. https://doi.org/10.1007/BF00482487

    Article  Google Scholar 

  6. Ward, A., Brogden, R.N., Heel, R.C., Speight, T.M., and Avery, G.S., Drugs, 1983, vol. 26, no. 6, p. 468. https://doi.org/10.2165/00003495-198326060-00002

    Article  CAS  Google Scholar 

  7. Verissimo, E., Berry, N., Gibbons, P., Lurdes, S., Cristiano, M., Rosenthal, P.J., Gut, J., Ward, S.A., and O’Neill, P.M., Bioorg. Med. Chem. Lett., 2008, vol. 18, no. 14, p. 4210. https://doi.org/10.1016/j.bmcl.2008.05.068

    Article  CAS  Google Scholar 

  8. Ettari, R., Bonaccorso, C., Micale, N., Heindl, C., Schirmeister, T., Calabrò, M.L., Grasso, S., and Zappalà, M., ChemMedChem., 2011, vol. 6, no. 7, p. 1228. https://doi.org/10.1002/cmdc.201100093

    Article  CAS  Google Scholar 

  9. Yildiz-Oren, I., Yalcin, I., Aki-Sener, E., and Ucarturk, N., Eur. J. Med. Chem., 2004, vol. 39, no. 3, p. 291. https://doi.org/10.1016/j.ejmech.2003.11.014

    Article  CAS  Google Scholar 

  10. Clark, R.L., Pessolano, A.A., Witzel, B., Lanza, T., and Shen, T.Y., J. Med. Chem., 1978, vol. 21, p. 1158. https://doi.org/10.1021/jm00209a014

    Article  CAS  Google Scholar 

  11. Boger, D.L., Miyauchi, H., Du, W., Hardouin, C., Fecik, R.A., Cheng, H., Hwang, I., Hedrick, M.P., Leung, D., Acevedo, O., Guimarães, C.R.W., Jorgensen, W.L., and Cravatt, B.F., J. Med. Chem., 2005, vol. 48, no. 6, p. 1849. https://doi.org/10.1021/jm049614v

    Article  CAS  Google Scholar 

  12. Doise, M., Blondeau, D., and Sliwa, H., Synth. Commun., 1992, vol. 22, no., 20, p. 2891. https://doi.org/10.1080/00397919208021112

    Article  CAS  Google Scholar 

  13. Myllymäki, M.J. and Koskinen, A.M.P., Tetrahedron Lett., 2007, vol. 48, no. 13, p. 2295. https://doi.org/10.1016/j.tetlet.2007.01.161

    Article  Google Scholar 

  14. Dan Xu, Xianfang Xu, Zongliang Liu, Li-Ping Sun, and Qidong You., Synlett., 2009, vol. 7, p. 1172. https://doi.org/10.1055/s-0028-1088149

    Google Scholar 

  15. Kulakov, I.V., Matsukevich, M.V., Shulgau, Z.T., Sergazy, S., Seilkhanov, T.M., Puzari, A., and Fisyuk, A.S., Chem. Heterocycl. Compd., 2015, vol. 51, p. 991. https://doi.org/10.1007/s10593-016-1809-7

    Article  CAS  Google Scholar 

  16. Fisyuk, A.S., Kulakov, I.V., Goncharov, D.S., Nikitina, O.S., Bogza, Y.P., and Shatsauskas, A.L., Chem. Heterocycl. Compd., 2014, vol. 50, no. 2, p. 217. https://doi.org/10.1007/s10593-014-1464-9

    Article  CAS  Google Scholar 

  17. Palamarchuk, I.V., Matsukevich, M.V., Kulakov, I.V., Seilkhanov, T.M., and Fisyuk, A.S., Chem. Heterocycl. Compd., 2019, vol. 55, no. 8, p. 788. https://doi.org/10.1007/s10593-019-02537-y

    Article  CAS  Google Scholar 

  18. Kulakov, I.V., Nurkenov, O.A., Turdybekov, D.M., and Turdybekov, K.M., Chem. Nat. Compd., 2010, vol. 46, no. 2, p. 257. https://doi.org/10.1007/s10600-010-9582-9

    Article  CAS  Google Scholar 

  19. Kulakov, I.V., Nurkenov, O.A., Turdybekov, D.M., Ainabaev, A.A., Turdybekov, K.M., and Gazaliev, A.M., Chem. Nat. Compd., 2009, vol. 45, no. 1, p. 66. https://doi.org/10.1007/s10600-009-9251-z

    Article  CAS  Google Scholar 

  20. Kulakov, I.V., Nurkenov, O.A., Turdybekov, D.M., Ibragimov, B.T., Talipov, S.A., Zhambekov, Z.M., Ainabaev, A.A., and Turdybekov, K.M., Chem. Nat. Compd., 2009, vol. 45, no. 2, p. 209. https://doi.org/10.1007/s10600-009-9284-3

    Article  CAS  Google Scholar 

  21. Kulakov, I.V., Nurkenov, O.A., Arinova, A.E., Turdybekov, D.M., Talipov, S.A., and Ibragimov, B.T., Chem. Nat. Compd., 2011, vol. 47, no. 5, p. 777. https://doi.org/10.1007/s10600-011-0056-5

    Article  CAS  Google Scholar 

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Funding

This study was financially supported by the Russian Foundation for Basic Research (project no. 18-33-01143).

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Correspondence to I. V. Palamarchuk.

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Palamarchuk, I.V., Ogurtsova, D.N., Seilkhanov, T.M. et al. Synthesis of N-Derivatives of Cytisine, Anabasine, and Salsoline Alkaloids with Pharmacophore 3-Aminopyridine-2(1H)-one and 5-Methyl-7-phenyloxazole[5,4-b]pyridine Cycles. Russ J Gen Chem 89, 2487–2491 (2019). https://doi.org/10.1134/S1070363219120259

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