New A-seco-lupane C-3 amide conjugates were prepared by the reaction of 28-methoxy-28-oxo-1-cyano2,3-seco-lup-20(29)-en-3-oic acid chloride with primary amines and synthetic and natural amino acids. Ethyl-N-[28-methyl-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oyl]-β-alaninate, which was cytotoxic against rhabdomyosarcoma tumor cells (IC50 47.5 μM), in addition to ethyl-N-[28-methoxy-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oyl]glycinate and N-[28-methyl-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oyl]-2-aminothiazole, which inhibited reproduction of herpes simplex virus type 1 (EC50 35.1 and 30.9 1 M, respectively), were selected.
Similar content being viewed by others
References
W. J. Baas, Phytochemistry, 24(9), 1875 (1985).
M. Urban, J. Sarek, J. Klinot, G. Korinkova, and M. Hajduch, J. Nat. Prod., 67, 1100 (2004).
O. B. Kazakova, E. F. Khusnutdinova, O. S. Kukovinets, T. I. Zvereva, and G. A. Tolstikov, Khim. Prir. Soedin., 333 (2010).
I. A. Tolmacheva, V. V. Grishko, E. I. Boreko, O. V. Savinova, and N. I. Pavlova, Khim. Prir. Soedin., 566 (2009).
Y. Wei, C.-M. Ma, and M. Hattori, Bioorg. Med. Chem., 17(8), 3003 (2009).
Y. Wei, C.-M. Ma, and M. Hattori, Eur. J. Med. Chem., 44(10), 4112 (2009).
M. Urban, J. Sarek, I. Tislerova, P. Dzubak, and M. Hajduch, Bioorg. Med. Chem., 13, 5527 (2005).
N. V. Galaiko, I. A. Tolmacheva, V. V. Grishko, L. V. Volkova, E. N. Perevozchikova, and S. A. Pestereva, Bioorg. Khim., 36(4), 556 (2010).
I. A. Tolmacheva, E. V. Igosheva, V. V. Grishko, O. S. Zhukova, and G. K. Gerasimova, Bioorg. Khim., 36(3), 410 (2010).
D. A. Scudiero, R. H. Shoemaker, K. D. Paull, A. Monks, S. Tierney, T. H. Notziger, M. T. Currens, D. Seniff, and M. K. Boyd, Cancer Res., 48, 4827 (1988).
B. Keil, Laboratoriumstechnik der Organische Chemie, Akademie-Verlag, Berlin, 1961.
I. A. Tolmacheva, A. V. Nazarov, O. A. Maiorova, and V. V. Grishko, Khim. Prir. Soedin., 491 (2008).
E. I. Boreko, N. I. Pavlova, G. V. Zaitseva, and I. A. Mikhailopulo, Vopr. Virusol., 5, 40 (2001).
K. P. Fung, Comput. Biol. Med., 19(2), 131 (1989).
P. G. Rytik, G. van der Groen, V. F. Eremin, N. D. Kolomiets, S. A. Popov, P. Nijs, V. Willems, G. Verkauteren, Yu. G. Il′kevich, and N. N. Lemeshko, Vopr. Virusol., 35(5), 389 (1990).
I. I. Kucherov, P. G. Rytik, and I. A. Podol′skaya, in: Proceedings of the IInd Scientific-Practical Conf. on Progress of GNTP Infectious Diseases, 1998–2000, Minsk, 2001, p. 195.
R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, and E. De Clereq, J. Virol. Methods, 20(4), 309 (1988).
Acknowledgment
The work was supported financially by State Contract No. 11.519.11.2033; RFBR Grant No. 10-03-96044; and the Ministry of Education, Perm Territory, for the performance of the MIG scientific project.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2012, pp. 385–389.
Rights and permissions
About this article
Cite this article
Igosheva, E.V., Tolmacheva, I.A., Vikharev, Y.B. et al. Synthesis and biological activity of amides of 28-methoxy-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oic acid. Chem Nat Compd 48, 426–431 (2012). https://doi.org/10.1007/s10600-012-0266-5
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-012-0266-5