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Synthesis of lupane triterpenoids with triphenylphosphonium substituents and studies of their antitumor activity

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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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References

  1. 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).

    CAS  Google Scholar 

  2. 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].

    CAS  Google Scholar 

  3. P. Yogeeswari, D. Sriram, Curr. Med. Chem., 2005, 12, 657.

    Article  CAS  Google Scholar 

  4. 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.

    Article  CAS  Google Scholar 

  5. R. A. Cichewicz, S. A. Kouzi, Med. Res. Rev., 2004, 24, 90.

    Article  CAS  Google Scholar 

  6. R. Mukherjee, V. Kumar, S. K. Srivastava, S. K. Agarwal, A. C. Burman, Anti-Cancer Agents Med. Chem., 2006, 6, 271.

    Article  CAS  Google Scholar 

  7. S. Fulda, Int. J. Mol. Sci., 2008, 9, 1096.

    Article  CAS  Google Scholar 

  8. 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.

    Article  CAS  Google Scholar 

  9. S. Fulda, G. Kroemer, Drug Discovery Today, 2009, 14, 885.

    Article  CAS  Google Scholar 

  10. F. B. Mullauer, J. H. Kessler, J. P. Medema, Anticancer Drugs, 2010, 21, 215.

    Article  CAS  Google Scholar 

  11. F. Wang, M. A. Ogasawara, P. Huang, Mol. Aspects Med., 2010, 31, 75.

    Article  CAS  Google Scholar 

  12. L. Biasutto, L.-F. Dong, M. Zoratti, J. Neuzil, Mitochondrion, 2010, 10, 670.

    Article  CAS  Google Scholar 

  13. B. Bachowska, J. Kazmierczak-Baranska, M. Cieslak, B. Nawrot, D. Szczesna, J. Skalik, P. Balczewski, Chemistryopen, 2012, 1, 33.

    Article  CAS  Google Scholar 

  14. M. Millard, D. Pathania, Y. Shabaik, L. Taheri, J. Deng, N. Neamati, PLoS ONE, 2010, 5, e13131.

    Article  Google Scholar 

  15. 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.

    Article  CAS  Google Scholar 

  16. S. J. Ralph, J. Neuzil, Patent Aplication Publication № US 2011/0105437 A1; http://www.faqs.org/patents/app/20110105437.

  17. DSHL. Kim, Z. Chen, V. T. Ngugen, J. M. Pezzuto, S. Qui, Z.-Z. Lu, Synt. Commun., 1997, 27, 1607.

    Article  CAS  Google Scholar 

  18. M. Urban, J. Sarek, J. Klinot, G. Kornikova, M. Hajduch, J. Nat. Prod., 2004, 67, 1100.

    Article  CAS  Google Scholar 

  19. 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.

    Article  CAS  Google Scholar 

  20. 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].

    Article  CAS  Google Scholar 

  21. 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].

    Google Scholar 

  22. J. L. Luche, J. Am. Chem. Soc., 1978, 100, 2226.

    Article  CAS  Google Scholar 

  23. E. St’astna, I. Cerny, V. Pouzar, H. Chodounska, Steroids, 2010, 75, 721.

    Article  Google Scholar 

  24. 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].

    CAS  Google Scholar 

  25. J. J. Kiddle, Tetrahedron Lett., 2000, 41, 1339.

    Article  CAS  Google Scholar 

  26. T. R. Mosmann, J. Immunol. Methods, 1983, 5, 55.

    Article  Google Scholar 

  27. 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].

    CAS  Google Scholar 

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Correspondence to A. Yu. Spivak.

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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

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