Skip to main content
SpringerLink
Log in

Crystal structure of new carboxylate phosphabetaines and phosphonium salts conjugated with them

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Earlier unknown crystalline forms of three carboxylate phosphabetaines and conjugated with them phosphonium salts differing by β substituent with respect to the carboxylate group were studied. The structure of studied compounds in crystal is determined by intermolecular electrostatic interactions. This leads to the trans arrangement of the carboxylate and the phosphonium groups.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. T. Aniszewski, Alkaloids — Secrets of Life: Alkaloid Chemistry, Biological Significance, Applications and Ecological Role, 1st ed, Amsterdam, Elsevier Science, 2007, 335 pp.

    Google Scholar 

  2. G. A. Cordell, The Alkaloids, 64, Elsevier Science, 2007, 248 pp.

    Google Scholar 

  3. Z. Wang, E. Klipfell, B. J. Bennett, R. Koeth, B. S. Levison, B. DuGar, A. E. Feldstein, E. B. Britt, X. Fu, Y.-M. Chung, Y. Wu, P. Schauer, J. D. Smith, H. Allayee, W. H. Wilson Tang, J. A. DiDonato, A. J. Lusis, S. L. Hazen, Nature, 2011, 472, 57.

    Article  CAS  Google Scholar 

  4. E. K. Perttu, A. G. Kohli, F. C. Szoka, J. Am. Chem. Soc., 2012, 134, 4485.

    Article  CAS  Google Scholar 

  5. X. Yu, J. Zheng, J. Mol. Biol., 2012, 421, 561.

    Article  CAS  Google Scholar 

  6. F. Mollinedo, C. Gajate, S. Marthn-Santamaria, F. Gago, Curr. Med. Chem., 2004, 11, 3163.

    Article  CAS  Google Scholar 

  7. S. Azzouz, M. Maache, R. G. Garcia, A. Osuna, Basic and Clinical Pharmacol. and Toxicology, 2005, 96, 60.

    Article  CAS  Google Scholar 

  8. S. B. Kondapaka, S. S. Singh, G. P. Dasmahapatra, E. A. Sausville, K. K. Roy, Mol. Cancer Ther., 2003, 2, 1093.

    CAS  Google Scholar 

  9. T. P. Dorlo, P. P. Van Thiel, A. D. Huitema, R. J. Keizer, H. J. deVries, J. H. Beijnen, P. J. deVries, Antimicrob. Agents Chemother, 2008, 52, 2855.

    Article  CAS  Google Scholar 

  10. F. Widmer, L. Wright, D. Obando, R. Handke, R. Ganendren, D. Ellis, T. Sorrell, Antimicrob. Agents Chemother, 2006, 50, 414.

    Article  CAS  Google Scholar 

  11. K. Barhwal, S. K. Hota, V. Jain, D. Prasad, S. B. Singh, G. Ilavazhagan, Neuroscience, 2009, 161, 501.

    Article  CAS  Google Scholar 

  12. V. V. Floch, S. Loisel, E. Guénin, A. C. Hervé, J. C. Clément, J. J. Yaouanc, H. des Abbayes, C. Férec, J. Med. Chem., 2000, 43, 4617.

    Article  CAS  Google Scholar 

  13. E. Guйnin, A. C. Hervé, V. V. Floch, S. Loisel, J. J. Yaouanc, J. C. Clйment, C. Fйrec, H. des Abbayes, Angew. Chem., Int. Ed., 2000, 39, 629.

    Article  Google Scholar 

  14. A. Fraix, T. Montier, T. L. Gall, C. M. Sevrain, N. Carmoy, M. F. Lindberg, P. Lehnb, P.-A. Jaffrès, Org. Biomol. Chem., 2012, 10, 2051.

    Article  CAS  Google Scholar 

  15. Yu. Strobykina, M. G. Belenok, M. N. Semenova, V. V. Semenov, V. M. Babaev, I. Kh. Rizvanov, V. F. Mironov, V. E. Kataev, J. Natur. Prod., 2015, 78, 1300.

    Article  CAS  Google Scholar 

  16. E. A. Chugunova, R. E. Mukhamatdinova, A. R. Burilov, Russ. J. Gen. Chem. (Engl. Transl.), 2015, 85, 1201 [Zh. Obshch. Khim., 2015, 85, 872].

    Article  CAS  Google Scholar 

  17. T. Sakurai, K. Fujiwara, Br. J. Pharmacol., 2001, 132, 143.

    Article  CAS  Google Scholar 

  18. J. S. Edmonds, K. A. Francesconi, Appl. Organometal. Chem., 1988, 2, 297.

    Article  CAS  Google Scholar 

  19. C. Kojima, T. Sakurai, M. Ochiai, H. Kumata, W. Qu, M. P. Waalkes, K. Fujiwara, Appl. Organometal. Chem., 2002, 16, 421.

    Article  CAS  Google Scholar 

  20. T. Rezanka, K. Sigler, Phytochemistry, 2008, 69, 585.

    Article  CAS  Google Scholar 

  21. A. Mattarei, L. Biasutto, E. Marotta, U. De Marchi, N. Sassi, S. Garbisa, M. Zoratti, C. Paradisi, ChemBioChem., 2008, 9, 2633.

    Article  CAS  Google Scholar 

  22. S. Rodriguez-Cuenca, H. M. Cochemé, A. Logan, I. Abakumova, T. A. Prime, C. Rose, A. Vidal-Puig, A. C. Smith, D. C. Rubinsztein, I. M. Fearnley, B. A. Jones, S. Pope, S. J. R. Heales, B. Y. H. Lam, S. Guha Neogi, I. McFarlane, A. M. James, R. A. J. Smith, M. P. Murphy, Free Radical Biol. Med., 2010, 48, 161.

    Article  CAS  Google Scholar 

  23. J. Ripcke, K. Zarse, M. Ristow, M. Birringer, ChemBioChem., 2009, 10, 1689.

    Article  CAS  Google Scholar 

  24. I. V. Galkina, A. I. Tufatullin, D. B. Krivolapov, Y. V. Bakhtiyarova, D. R. Chubukaeva, V. V. Stakheev, V. I. Galkin, R. A. Cherkasov, B. Büchner, O. N. Kataeva, Cryst. Eng. Comm., 2014, 16, 9010.

    Article  CAS  Google Scholar 

  25. V. I. Galkin, Yu. V. Bakhtiyarova, N. A. Polezhaeva, I. V. Galkina, R. A. Cherkasov, D. B. Krivolapov, A. T. Gubaydullin, I. A. Litvinov, Russ. J. Gen. Chem. (Engl. Transl.), 2002, 72, 376 [Zh. Obshch. Khim., 2002, 72, 404].

    Article  CAS  Google Scholar 

  26. V. I. Galkin, Yu. V. Bakhtiyarova, N. A. Polezhaeva, R. A. Cherkasov, D. B. Krivolapov, A. T. Gubaidullin, I. A. Litvinov, Phosphorus, Sulfur, Silicon Relat. Elem., 1999, 147, 91.

    Article  Google Scholar 

  27. V. I. Galkin, Yu. V. Bakhtiyarova, N. A. Polezhaeva, I. V. Galkina, R. A. Cherkasov, D. B. Krivolapov, A. T. Gubaydullin, I. A. Litvinov, Russ. J. Gen. Chem. (Engl. Transl.), 2002, 72, 384 [Zh. Obshch. Khim., 2002, 72, 412].

    Article  CAS  Google Scholar 

  28. V. I. Galkin, Yu. V. Bakhtiyarova, R. I. Sagdieva, I. V. Galkina, R. A. Cherkasov, D. B. Krivolapov, A. T. Gubaydullin, I. A. Litvinov, Russ. J. Gen. Chem. (Engl. Transl.), 2006, 76, 430 [Zh. Obshch. Khim., 2006, 76, 452].

    Article  CAS  Google Scholar 

  29. Yu. V. Bakhtiyarova, R. I. Sagdieva, I. V. Galkina, V. I. Galkin, R. A. Cherkasov, D. B. Krivolapov, A. T. Gubaidullin, I. A. Litvinov, Russ. J. Gen. Chem. (Engl. Transl.), 2007, 43, 207 [Zh. Obshch. Khim., 2007, 43, 215].

    Article  CAS  Google Scholar 

  30. S.-L. Li, T.C.W. Mak, J. Mol. Struct., 1996, 384, 135.

    Article  CAS  Google Scholar 

  31. L. Leiserowitz, Acta Cryst., 1976, B32, 775.

    Article  CAS  Google Scholar 

  32. E. V. Mironova, M. S. Dzyurkevich, O. A. Lodochnikova, D. B. Krivolapov, I. A. Litvinov, V. V. Plemenkov, Russ. J. Struct. Chem. (Engl. Transl.), 2012, 53, 361 [Zh. Struktur. Khim., 2012, 53, 360].

    Article  CAS  Google Scholar 

  33. G. M. Sheldrick, SADABS, University of Göttingen, Germany, 2004.

    Google Scholar 

  34. G. M. Sheldrick, Acta Crystallogr., Sect. A, 2008, 64, 112.

    Article  CAS  Google Scholar 

  35. L. J. Farrugia, J. Appl. Cryst., 1999, 32, 837.

    Article  CAS  Google Scholar 

  36. APEX2 (Version 2.1), SAINTPlus: Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-Ray Solutions, Bruker AXS Inc., Madison, Wisconsin, USA, 2006.

Download references

Author information

Authors and Affiliations

  1. A. M. Butlerov Chemical Institute of Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    Yu. V. Bakhtiyarova, A. F. Aksunova, I. V. Galkina & V. I. Galkin

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    O. A. Lodochnikova & O. N. Kataeva

Authors
  1. Yu. V. Bakhtiyarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. F. Aksunova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. V. Galkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. I. Galkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. A. Lodochnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. O. N. Kataeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Galkina.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. G. Sinyashin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1313–1318, May, 2016.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bakhtiyarova, Y.V., Aksunova, A.F., Galkina, I.V. et al. Crystal structure of new carboxylate phosphabetaines and phosphonium salts conjugated with them. Russ Chem Bull 65, 1313–1318 (2016). https://doi.org/10.1007/s11172-016-1454-4

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-016-1454-4

Key words

Search

Navigation