Abstract
New derivatives of lupane triterpenoids, viz., 20,29-dihydrobetulinic and 3-epi-20,29-dihydrobetulinic acid derivatives containing triphenylphosphonium fragments as substituents were synthesized. These compound considerably exceed betulinic acid in antitumor activity.
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G. A. Tolstikov, O. B. Flekhter, E. E. Shul’ts, L. A. Baltina, A. G. Tolstikov, Khimiya v interesakh ustoichivogo razvitiya [Chemistry in the Interest of Stable Development], 2005, 13, 1 (in Russian).
T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, O. B. Flekhter, Bioorg. Khim., 2006, 32, 42 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2006, 32, No. 1].
P. Yogeeswari, D. Sriram, Curr. Med. Chem., 2005, 12, 657.
E. Pisha, H. Chai, I.-S. Lee, T. E. Chagwedera, N. R. Farnsworth, G. A. Cordell, C. W. W. Beecher, H. H. S. Fong, A. D. Kinghorn, D. M. Brown, M. C. Wani, M. E. Wall, T. J. Hieken, T. K. Das Gupta, J. M. Pezzuto, Nat. Med., 1995, 1, 1046.
R. A. Cichewicz, S. A. Kouzi, Med. Res. Rev., 2004, 24, 90.
R. Mukherjee, V. Kumar, S. K. Srivastava, S. K. Agarwal, A. C. Burman, Anti-Cancer Agents Med. Chem., 2006, 6, 271.
S. Fulda, Int. J. Mol. Sci., 2008, 9, 1096.
J. Neuzil, L.-F. Dong, L. Ramanathapuram, T. Hahn, M. Chladova, X.-F. Wang, R. Zobalova, L. Prochazka, M. Gold, R. Freeman, J. Turanek, E. T. Akporiaye, J. C. Dyason, S. J. Ralphf, Mol. Aspects Med., 2007, 28, 607.
S. Fulda, G. Kroemer, Drug Discovery Today, 2009, 14, 885.
F. B. Mullauer, J. H. Kessler, J. P. Medema, Anticancer Drugs, 2010, 21, 215.
F. Wang, M. A. Ogasawara, P. Huang, Mol. Aspects Med., 2010, 31, 75.
L. Biasutto, L.-F. Dong, M. Zoratti, J. Neuzil, Mitochondrion, 2010, 10, 670.
B. Bachowska, J. Kazmierczak-Baranska, M. Cieslak, B. Nawrot, D. Szczesna, J. Skalik, P. Balczewski, Chemistryopen, 2012, 1, 33.
M. Millard, D. Pathania, Y. Shabaik, L. Taheri, J. Deng, N. Neamati, PLoS ONE, 2010, 5, e13131.
A. Manetta, G. Gamboa, A. Nasseri, Y. D. Podnos, D. Emma, G. Dorion, L. Rawlings, P. M. Carpenter, A. Bustamante, J. Patel, D. Rideout, Gynecologic Oncology, 1996, 60, 203.
S. J. Ralph, J. Neuzil, Patent Aplication Publication № US 2011/0105437 A1; http://www.faqs.org/patents/app/20110105437.
DSHL. Kim, Z. Chen, V. T. Ngugen, J. M. Pezzuto, S. Qui, Z.-Z. Lu, Synt. Commun., 1997, 27, 1607.
M. Urban, J. Sarek, J. Klinot, G. Kornikova, M. Hajduch, J. Nat. Prod., 2004, 67, 1100.
C. Genet, A. Strehle, C. Schmidt, G. Boudjelal, A. Lobstein, K. Schoonjans, M. Souchet, J. Auwerx, R. Saladin, A. Wagner, J. Med. Chem., 2010, 53, 178.
A. Yu. Spivak, E. R. Shakurova, D. A. Nedopekina, R. R. Khalitova, L. M. Khalilov, V. N. Odinokov, Yu. P. Bel’skii, A. N. Ivanova, N. V. Bel’skaya, M. G. Danilets, A. A. Ligacheva, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 694 [Izv. Akad. Nauk, Ser. Khim., 2011, 680].
O. B. Flekhter, L. R. Nigmatullina, L. A. Baltina, L. T. Karachurina, F. Z. Galin, F. S. Zarudii, G. A. Tolstikov, E. I. Boreko, N. I. Pavlova, S. N. Nikolaeva, O. V. Savinova, Khim. Farm. Zh., 2002, 36, 26 [Pharm. Chem. J. (Engl. Transl.), 2002, 36].
J. L. Luche, J. Am. Chem. Soc., 1978, 100, 2226.
E. St’astna, I. Cerny, V. Pouzar, H. Chodounska, Steroids, 2010, 75, 721.
A. V. Symon, A. P. Kaplun, N. K. Vlasenkova, G. K. Gerasimova, Le Bang Shon, E. F. Litvin, L. M. Kozlova, E. L. Surkova, V. I. Shvets, Bioorg. Khim., 2003, 29, 208 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2003, 29].
J. J. Kiddle, Tetrahedron Lett., 2000, 41, 1339.
T. R. Mosmann, J. Immunol. Methods, 1983, 5, 55.
G. A. Tolstikov, M. I. Goryaev, Kh. O. Kim, R. A. Khegai, Zh. Prikl. Khim., 1967, 40, 920 [Russ. J. Appl. Chem. (Engl. Transl.), 1967, 40].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0189–0199, January, 2013.
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Spivak, A.Y., Nedopekina, D.A., Shakurova, E.R. et al. Synthesis of lupane triterpenoids with triphenylphosphonium substituents and studies of their antitumor activity. Russ Chem Bull 62, 188–198 (2013). https://doi.org/10.1007/s11172-013-0028-y
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DOI: https://doi.org/10.1007/s11172-013-0028-y