Synthesis, Structure, and Biological Activity of Cinnamoyl-Containing Cytisine and Anabasine Alkaloids Derivatives
Article
First Online:
- 9 Downloads
Abstract
The reactions of the cytisine and anabasine alkaloids with cinnamic acid chloride have been studied, and hydrazinolysis of the resulting N-cinnamoylcytisine and N-cinnamoylanabazine has been carried out. The reaction of cinnamoyl isothiocyanate with alkaloids has afforded the corresponding thiourea derivatives. Antimicrobial and cytotoxic activity of cinnamoyl-containing derivatives of these alkaloids has been evaluated.
Keywords
cytisine anabasine N-cinnamoylcytisine N-cinnamoylanabasine cinnamoyl chloridePreview
Unable to display preview. Download preview PDF.
Notes
Funding
This study was financially supported by the Committee for Science, Ministry of Education and Science of Kazakhstan (PTsF no. BR05236438-OT-18).
Conflict of Interest
No conflict of interest was declared by the authors.
References
- 1.Tlegenov, R., Doctoral (Chem.) Dissertation, Tashkent, 2008. 54 s.Google Scholar
- 2.Primuhamedov, Z.I. and Tillyaev, K.S., Uzb. Khim. Zh., 1981, no. 1, p. 52.Google Scholar
- 3.Primuhamedov, Z.I., Tillyaev, K.S., and Zaidova, R.A., Uzb. Khim. Zh., 1982, no. 3, p. 63; Saprikina, V.A., Vinogradova, V.I., Ambartsumova, R.F., Ibragimov, T.F., and Shakhidoyatov, Kh.M., Chem. Nat. Compd., 2004, no. 4, p. 276. https://doi.org/10.1007/s10600-006-0182-7 CrossRefGoogle Scholar
- 4.Abduvakhabov, A.A., Sadykov, A.A., Dalimov, D.N., and Aslanov, H.A., Alkaloidy i ikh proizvodnye kak instrument dlya izucheniya kholinergicheskoi sistemy (Alkaloids and Their Derivatives as a Tool for Studying the Cholinergic System), Tashkent: Fan, 1984.Google Scholar
- 5.RF Patent 2440997, 2012; Buyll. Izobret., 2012, no. 3.Google Scholar
- 6.Saprikina, V.A., Vinogradova, V.I., Ambartsumova, R.F., Ibragimov, T.F., Sultankulova, A., and Shakhidoyatov, Kh.M., Chem. Nat. Compd., 2004, no. 6, p. 582. https://doi.org/10.1007/s10600-005-0042-x CrossRefGoogle Scholar
- 7.Abdullaev, N.P., Makhmudov, U.S., Tashkhodzhaev, B., Genzhemuratova, G., Levkovich, M.G., and Shakhidoyatov, Kh.M., Chem. Nat. Compd., 2009, no. 6, p. 837. https://doi.org/10.1007/s10600-010-9495-7 CrossRefGoogle Scholar
- 8.Nurkenov, O.A., Kulakov, I.V., and Fazylov, S.D., Sinteticheskie transformatsii alkaloida tsitizina (Synthetic Transformations of Cytisine Alkaloid), Karaganda: Glasir, 2012.Google Scholar
- 9.Nurkenov, O.A., Fazylov, S.D., Kulakov, I.V., and Musina, L.A., Alkaloid anabazin i ego proizvodnye (Anabazine Alkaloid and Its Derivatives), Karaganda: Glasir, 2010.Google Scholar
- 10.Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc. Perkin Trans. 2, 1987, vol. 2, no. 12, p. 1. https://doi.org/10.1039/P298700000S1 Google Scholar
- 11.Wojciechowska-Nowak, M., Boczon, W., Rychlewska, U., and Warzajtis, B., J. Mol. Struct., 2007. 840, p. 44. https://doi.org/10.1016/j.molstruc.2006.11.037 CrossRefGoogle Scholar
- 12.Wojciechowska-Nowak, M., Jasiewicz, B., Boczon, W., and Rychlewska, U., J. Mol. Struct., 2011. 997, p. 15. https://doi.org/10.1016/j.molstruc.2011.04.015 CrossRefGoogle Scholar
- 13.Nurkenov, O.A., Satpaeva, Zh.B., Fazylov, S.D., Seilkhanov, T.M., Turdybekov, K.M., Turdybekov, D.M., Akhmetova, S.B., Makhmutova, A.S., and Gazaliev, A.M., Chem. Nat. Compd., 2016, vol. 52, no. 2, p. 276. https://doi.org/10.1007/s10600-016-1613-8 CrossRefGoogle Scholar
- 14.Zefirov, Yu.V. and Zorkii, P.M., Zh. Strukt. Khim., 1974, vol. 15, no. 1, p. 118.Google Scholar
- 15.Takagi, K., Tanaka, M., Murakami, Y., Morita, H., and Aotsuka, T., Eur. J. Med. Chem. Chim. Ther., 1986, vol. 21, p. 65.Google Scholar
- 16.Ankhiwala, M.D. and Naik, H.B., J. Indian Chem. Soc., 1990, vol. 67, no. 3, p. 258. https://doi.org/10.1002/chin.199049179 Google Scholar
- 17.Kaname, T., Masaaki, T., Hikari, M., Kuniyoshi, O., Katsuyuki, I., Naoki, N., and Masayuki, O., Eur. J. Med. Chem., 1987, vol. 22, p. 239. https://doi.org/10.1016/0223-5234(87)90055-9 CrossRefGoogle Scholar
- 18.Navashin, S.M. and Fomina, I.P., Ratsional’naya antibiotikoterapiya. Spravochnik (Rational Antibiotic Therapy. Handbook), Moscow: Meditsina, 1982.Google Scholar
- 19.Meyer, B.N., Ferrigni, N.R., Putnam, J.E., Jacobsen, L.B., Nicholsand, D.E., and McLaughlin, J.L., Planta Medica, 1982, vol. 45, p. 31.CrossRefGoogle Scholar
- 20.McLaughlin, J.L., Methods Plant Boichem., 1991, vol. 6, p. 1.Google Scholar
- 21.Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques and References, New York: Wiley, 1972.Google Scholar
- 22.CrysAlisPro, Aligent Technologies, Version 1.171.37.34 (release 2014).Google Scholar
- 23.Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. https://doi.org/10.1107/s0108767307043930 CrossRefGoogle Scholar
- 24.Sheldrick, G.M., Acta Crystallogr. (C), 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218 Google Scholar
Copyright information
© Pleiades Publishing, Ltd. 2019