Abstract
Efficient and versatile synthetic procedures towards novel derivatives of betulonic acid via Mannich reaction, Sonogashira cross-coupling, and copper(i)-catalyzed 1,3-dipolar cyclo-additions were developed. Introduction of secondary amines (Mannich reaction) into betulonic acid amides led to derivatives possessing marked spasmolytic activity, which is not characteristic of the triterpene fragment.
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R. H. Cichewicz, S. A. Kouzi, Med. Res. Rev., 2004, 24, 90.
G. A. Tolstikov, O. B. Flekhter, E. E. Shultz, L. A. Baltina, A. G. Tolstikov, Chem. Sustainable Dev. (Engl. Transl.), 2005, 13, 1 [Khim. v Interesakh Ustoichivogo Razvitiya, 2005, 13, 1]; http://sibran.ru/en/journals/KhUR/.
P. Dzubak, M. Hajduch, D. Vydra, A. Hustova, M. Kvasnica, D. Biedermann, L. Markova, M. Urban, J. Sarek, Nat. Prod. Rep., 2006, 23, 394.
V. M. Dembitsky, D. O. Levitsky, Nat. Prod. Commun., 2006, 1, 405.
Acetylene Chemistry: Chemistry, Biology and Material Science, Eds C. F. Diederich, P. J. Stang, R. R. Tykwinski, Wiley–VCH, Weinheim, 2005, 508 pp.
S. F. Vasilevsky, A. I. Govdi, E. E. Shults, M. M. Shakirov, I. V. Sorokina, T. G. Tolstikova, D. S. Baev, G. A. Tolstikov, I. V. Alabugin, Bioorg. Med. Chem., 2009, 17, 5164.
A. I. Govdi, I. V. Sorokina, T. G. Tolstikova, S. F. Vasilevsky, G. A. Tolstikov, Chem. Sustainable Dev. (Engl. Transl.), 2010, 18, 397 [Khim. v Interesakh Ustoichivogo Razvitiya, 2010, 18, 477]; http://sibran.ru/en/journals/KhUR/.
A. Lagunin, D. Filimonov, V. Poroikov, Multi-targeted Natural Products Evaluation Based on Biological Activity Prediction with PASS, Curr. Pharm. Des., 2010, 16, 1703.
V. M. Dembitsky, G. A. Tolstikov, A. G. Tolstikov, Chem. Sustainable Dev. (Engl. Transl.), 2003, 11, 341 [Khim. v Interesakh Ustoichivogo Razvitiya, 2003, 11, 341]; http://sibran.ru/en/journals/KhUR/.
D. L. Musso, M. J. Clarke, J. L. Kelley, G. E. Boswell, G. Chen, Org. Biomol. Chem., 2003, 1, 498.
S. F. Vasilevskii, P. A. Slabuka, E. G. Izyumov, M. S. Shvartsberg, I. L. Kotlyarevskii, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1972, 21, 2453 [Izv. Akad. Nauk, Ser. Khim., 1972, 2524].
V. V. Afanas´ev, N. B. Bespalova, I. P. Beletskaya, Ross. Khim. Zh. (Zh. Ross. Khim. O-va im. D. I. Mendeleeva), 2006, 50, No. 4, 81 [Mendeleev Chem. J. (Engl. Transl.), 2006, 50].
L. Brandsma, S. F. Vasilevsky, H. D. Verkruijsse, Application of Transition Metal Catalysts in Organic Synthesis, Springer, Berlin, 1998, 336 pp.
G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba, A. A. Genazzani, Med. Res. Rev., 2008, 28, 278.
C. W. Tornøe, M. Meldal, Chem. Rev., 2008, 108, 2952.
C. W. Tornøe, C. Cristensen, M. Meldal, J. Org. Chem., 2002, 67, 3057.
K. H. Kwon, A. Barve, S. Yu, M. T. Huang, Acta Pharmacol. Sin., 2007, 28, 1409.
T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, O. B. Flekhter, Russ. J. Bioorg. Chem. (Engl. Transl.), 2006, 32, 261 [Bioorg. Khim., 2006, 32, 291.
Rukovodstvo po eksperimental´nomu (doklinicheskomu) izucheniyu novykh farmakologicheskikh vechshestv [Manual on Experimental (Pre-clinical) Study of Pharmacological Substances], Meditsina, Moscow, 2005, 832 pp.
V. S. Kamyshnikov, Spravochnik po kliniko-khimicheskoi laboratornoi diagnostike [Handbook of Clinical and Biochemical Laboratory Diagnostics], Belarus´, Minsk, 2000, 2, 207 pp.
M. Kuroyanagi, M. Shiotsu, T. Ebihara, H. Kawai, A. Ueno, S. Fukushima, Chem. Pharm. Bull., 1986, 34, 4012.
N. I. Petrenko, N. V. Elantseva, V. Z. Petukhova, M. M. Shakirov, E. E. Shul´tz, G. A. Tolstikov, Chem. Nat. Compd. (Engl. Transl.), 2002, 38, 331 [Khim. Prir. Soedin., 2002, No. 4, 276].
J. R. Feldman, E. C. Wagner, J. Org. Chem., 1942, 7, 31.
P. S. Bailey, G. Nowlin, W. Bost, J. Am. Chem. Soc., 1951, 51, 4078.
N. J. Putochin, Chem. Ber., 1922, 55, 2749.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1327–1334, June, 2015.
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Govdi, A.I., Sorokina, I.V., Baev, D.S. et al. Acetylenic derivatives of betulonic acid amide as a new type of compounds possessing spasmolytic activity. Russ Chem Bull 64, 1327–1334 (2015). https://doi.org/10.1007/s11172-015-1013-4
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DOI: https://doi.org/10.1007/s11172-015-1013-4