Skip to main content
Log in

The First 1-Hydroxypropylidenebisphosphonic Acid with 1,8-Naphthyridinone Substituent: Synthesis and Structure

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

1-Hydroxy-3-(5,7-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-1-yl)propylidenebisphosphonic acid has been synthesized. The structure of the acid and its precursors synthesized for the first time, 3-(5,7-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-1-yl)propionic acid and the corresponding methyl ester, in the solid state and in the DMSO solution has been elucidated by means of vibrational (IR and Raman) and multinuclear (1H, 13C, and 31P) NMR spectroscopy.

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

Access this article

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. Russell, R.G.G., Bone, 2011, vol. 49, no. 1, p. 2. doi 10.1016/j.bone.2011.04.022

    Article  CAS  PubMed  Google Scholar 

  2. Demkowicz, S., Rachon, J., Dásko, M., and Kozak, W., RSC Adv., 2016, vol. 6, p. 7101. doi 10.1039/c5ra25446a

    Article  CAS  Google Scholar 

  3. Abdou, W.M. and Shaddy, A.A., Arkivoc, 2009, vol. 9, p. 145. doi 10.3998/ark.5550190.0010.910

    Google Scholar 

  4. Chmielewska, E. and Kafarski, P., Open Pharm. Sci. J., 2016, vol. 3. 56. doi 10.2174/1874844901603010056

  5. Matkovskaya, T.A., Popov, K.I., Yur’eva, E.A., Bisfosfonaty: svoistva, stroenie i primenenie v meditsine (Bisphosphonates: Properties, Structure, and Application in Medicine), Moscow: Khimiya., 2001.

    Google Scholar 

  6. Ebetino, F.H., Hogan, A.-M.L., Sun, S., Tsoumpra, M.K., Duan, X., Triffitt, J.T., Kwaasi, A.A., Dunford, J.E., Barnet, B.L., Oppermann, U., Lundy, M.W., Boyde, A., Kashemirov, B.A., McKenna, Ch.E., and Russel, R.G.G., Bone, 2011, vol. 49, p. 20. doi 10.1016/j.bone.2011.03.774

    Article  CAS  PubMed  Google Scholar 

  7. Ferrer-Casal, M., Li, C., Galizzi, M., Stortz, C.A., Szajnman, S.H., Docampo, R., Moreno, S.N.J., and Rodriguez, J.B., Bioorg. Med. Chem., 2014, vol. 22, no. 1, p. 398. doi 10.1016/j.bmc.2013.11.010

    Article  CAS  PubMed  Google Scholar 

  8. Cromartie, T.H., Fisher, K.J., and Grossman, J.N., Pestic. Biochem. Physiol., 1999, vol. 63, p. 114; Kafarski, P., Lejczak, B., and Forlani, G., Heteroatom. Chem., 2000, vol. 11, no. 7, p. 449. doi 10.1002/1098-1071(2000) 11:7<449::AID-HC3>3.0.CO;2-V

    Article  CAS  Google Scholar 

  9. Leon, A., Liu, L., Yang, Y., Hudock, M.P., Hall, P., Yin, F., Studer, D., Puan, K.-J., Morita, C.T., and Oldfield, E., J. Med. Chem., 2006, vol. 49, no. 25, p. 7331. doi 10.1021/jm060492b

    Article  CAS  PubMed  Google Scholar 

  10. Matczak-Jon, E. and Videnova-Adrabińska, V., Coord. Chem. Rev., 2005, vol. 249, nos. 21–22, p. 2458. doi 10.1016/j.ccr.2005.06.001; Galezowska, J. and Gumienna-Kontecka, E., Coord. Chem. Rev., 2012, vol. 256, p. 105. doi 10.1016/j.ccr.2011.07.002

  11. Motaleb, H.A., It, I., El-Tawoosy, M., and Mohamed, M.I., J. Label. Compd. Radiopharm., 2017, vol. 60, no. 11, p. 542. doi 10.1002/jlcr.3532; Aufaure, R., Hardoin, J., Millot, N., Motte, L., Lalatonne, Y., and Guénin, E., Chem. Eur. J., 2016, vol. 22, no. 45, p. 16022. doi 10.1002/chem.201602899; Neves, M., Teixeira, F.C., Antunes, I., Majkowska, A., Gano, L., and Santos, A.C., Appl. Radiat. Isot., 2011, vol. 69, p. 80.

    Article  CAS  Google Scholar 

  12. Kontecka, E.G., Jezierska, J., Lecouvey, M., Leroux, Y., and Kozlowski, H., J. Inorg. Biochem., 2002, vol. 89, p. 13; Crisponi, G., Nurchi, V.M., and Pivetta, T., J. Inorg. Biochem., 2008, vol. 102, p. 209.

    Article  Google Scholar 

  13. Litvinov, V.P., Adv. Heterocycl. Chem., 2006, vol. 91, p. 189; Margiotta, N., Savino, S., Gandin, V., Marzano, C., and Natile, G., Chem. Med. Chem., 2014, vol. 9, p. 1161. doi 10.1002/cmdc.201402028; Bolhofer, W.A., Hoffman, J.M., Habecker, C.N., Pietruszkiewicz, A.M., Cragoe, E.J., Jr. and Torchiana, M.L., J. Med. Chem., 1979, vol. 22, no. 3, p. 301.

    Article  CAS  Google Scholar 

  14. Matveeva, A.G., Starikova, Z.A., Aysin, R.R., Skazov, R.S., Matveev, S.V., Timofeeva, G.I., Passechnik, M.P., and Nifant’ev, E.E., Polyhedron, 2013, vol. 61, p. 172. doi 10.1016/j.poly.2013.05.035; Gan, X., Chi, S.-M., Mu, W.-H.,Yao, J.C., Quan, L., Li, C., Bian, Z.-Y., and Chen, Y., Dalton Trans., 2011, vol. 40, p. 7365. doi 10.1039/c0dt01747g; Kaur, B., Kaur, N., and Kumar, S., Coord. Chem. Rev., 2018, vol. 358, p. 13. doi 10.1016/j.ccr.2017.12.0020010-8545

    Article  CAS  Google Scholar 

  15. Goswami, S., Dey, S., Gallagher, J.F., Lough, A.J., García-Granda, S., Torre-Fernández, L., Alkorta, I., and Elguero, J., J. Mol. Struct., 2007, vol. 846, p. 97. doi 10.1016/j.molstruc.2007.01.024; Corbin, P.S., Zimmerman, S.C., Thiessen, P.A., Hawryluk, N.A., and Murray, T.J., J. Am. Chem. Soc., 2001, vol. 123, p. 10475. doi 10.1021/ja010638q

    Article  CAS  Google Scholar 

  16. Bellamy, L.J., Advances in Infrared Group Frequencies, Suffolk: Methuen & Co. Ltd., 1968.

    Google Scholar 

  17. Kabachnik, M.I., Medved’, T.Ya., Dyatlova, N.M., Polikarpov, Yu.M., Shcherbakov, B.K., and Belski, F.I., Bull. Acad. Sci. USSR. Div. Chem. Sci., 1978, vol. 27, p. 374.

    Article  Google Scholar 

  18. Shcherbakov, B.K., Belski, F.I., Gukasova, А.Yu., Polikarpov, Yu.M., and Kabachnik, M.I., Izv. Akad. Nauk, Ser. Khim., 1998, p. 1780.

    Google Scholar 

  19. Matveeva, A.G., Pasechnik, M.P., Petrovskii, P.V., Matveev, S.V., and Pisareva, S.A., Russ. Chem. Bull., 2000, vol. 49, no. 6, p. 1045. doi 10.1007/BF02494893

    Article  CAS  Google Scholar 

  20. Kumar, S.S. and Nangia, A., Cryst. Growth Des., 2014, vol. 14, p. 1865. doi 10.1021/cg5000205

    Article  CAS  Google Scholar 

  21. Teixrira, F.C., Lucas, C., Curto, M.J.M., Neves, M., Duarte, M.T., Andre, V., and Teixrira, A.P.S., J. Braz. Chem. Soc., 2013, vol. 24, p. 1295. doi 10.5935/0103-5053.20130164

    Google Scholar 

  22. Pasechnik, M.P., Matveeva, A.G., Artyushin, O.I., Tcarkova, K.V., and Bondarenko, N.A., Russ. Chem. Bull., 2018, vol. 67, no. 2, p. 382. doi 10.1007/s11172-018-2085-8; Pasechnik, M.P., Matveeva, A.G., Klemenkova, Z.S., Artyushin, O.I., Tcarkova, K.V., and Bondarenko, N.A., Russ. J. Gen. Chem., 2018, vol. 86, no. 7, p. 1369. doi 10.1134/S1070363218070034

    Article  CAS  Google Scholar 

  23. Bernstein, J., Stearns, B., Shaw, E., and Lott, W.A., J. Am. Chem. Soc., 1947, vol. 69, p. 1151. doi 10.1021/ja01197a048

    Article  CAS  PubMed  Google Scholar 

  24. Mangini, A. and Colonna, M., Gazz. Chim. Ital., 1943, vol. 73, p. 323.

    CAS  Google Scholar 

  25. Dutta, A.K., Neese, F., and Izsak, R., J. Chem. Phys., 2016, vol. 144, p. 034102. doi 10.1063/1.4939844; Weigend, F., Phys. Chem. Chem. Phys., 2006, vol. 8, p. 1057. doi10.1039/B515623H

    Article  CAS  PubMed  Google Scholar 

  26. Tao, J., Perdew, J.P., Staroverov, V.N., and Scuseria, G.E., Phys. Rev. Lett., 2003, vol. 91, p. 146401. doi 10.1103/PhysRevLett.91.146401

    Article  CAS  PubMed  Google Scholar 

  27. Grimme, S., Ehrlich, S., and Goerigk, L., J. Comput. Chem., 2011, vol. 32, p. 1456. doi 10.1002/jcc.21759; Grimme, S., Antony, J., Ehrlich, S., and Krieg, H., J. Chem. Phys., 2010.Vol. 132, p. 154104. doi 10.1063/1.3382344

    Article  CAS  PubMed  Google Scholar 

  28. Weigend, F. and Ahlrichs, R., Phys. Chem. Chem. Phys., 2005, vol. 7, p. 3297. doi 10.1039/B508541A

    Article  CAS  PubMed  Google Scholar 

  29. Neese, F., Comput. Mol. Sci., 2012, vol. 2, p. 73. doi 10.1002/wcms.81

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. G. Matveeva.

Additional information

Dedicated to the 110th anniversary of M.I. Kabachnik’s birth

Original Russian Text © G.V. Bodrin, M.P. Pasechnik, A.G. Matveeva, R.R. Aysin, S.V. Matveev, E.I. Goryunov, T.V. Strelkova, V.K. Brel, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1445–1452.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bodrin, G.V., Pasechnik, M.P., Matveeva, A.G. et al. The First 1-Hydroxypropylidenebisphosphonic Acid with 1,8-Naphthyridinone Substituent: Synthesis and Structure. Russ J Gen Chem 88, 1792–1799 (2018). https://doi.org/10.1134/S1070363218090050

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218090050

Keywords

Navigation