Synthesis and physical-chemical properties of 3-benzyl-8-propylxanthine and its water-soluble salts

Authors

  • E. K. Mikhal’chenko Zaporizhzhia State Medical University,
  • K. V. Аleksandrova Zaporizhzhia State Medical University,
  • S. V. Levich Zaporizhzhia State Medical University,

DOI:

https://doi.org/10.14739/2409-2932.2016.1.62005

Keywords:

Xanthines, Organic Synthesis, NMR-Spectroscopy

Abstract

Aim. Selection of basic compounds is a key moment of the novel drug substances development process. Nowadays, it is possible to model the properties of biologically active substances with the help of computer technologies and the special software. We selected 3-benzyl-8-propylxanthine as a promising basic compound with a large variability of further chemical modification by insertion of well-known pharmacophores. Our decision was based on in silico-calculations.

Materials and methods. This compound has been synthesized by condensation of 1-benzyl-5,6-diaminopyrimidine-2,4-dione with butanic acid. Then we obtained a number of water-soluble 3-benzyl-8-propylxanthinides-7 on the basis of initial substance. Synthesis has been made by reaction of 3-benzyl-8-propylxanthine with inorganic or organic bases in an aqueous or aqueous-alcoholic solution.

Conclusion. The structure of synthesized compounds has been proved using elemental analysis and 1H NMR-spectroscopy.

References

Orlov, V. D., Lipinson, V. V., & Ivanov, V. V. (2005) Medicinskaya khimiya [Medical chemistry]. Kharkiv: Folio. [in Ukrainian].

Kotte, S. Ch. Bose, Tulam, V. Kumar, Raghavan, Sh., Dubey, P. K., & Murali, P. M. (2012) Identification of novel inhibitors of 11B-hydroxysteroid dehydrogenase type 1from natural products library through docking and pharmacophore modeling. International Journal of Research in Pharmacy and Chemistry, 2(1), 137–145.

Shkoda, A. S., Levich, S. V., Aleksandrova, K. V. (2013) 8-Zamishcheni 3-benzylksantynu yak perspektyvni spoluky dlia poshuku biolohichno aktyvnykh rechovyn [8-Substituted 3-benzylxanthines as prospective compounds for search of biological active compounds]. Farmatsevtychnyi chasopys, 1(25), 23–28. [in Ukrainian].

Aleksandrova, K. V., Levich, S. V., Shkoda, O. S., & Diachkov, M. V. (2011) Syntez ta fizyko-khimichni vlastyvosti 3-fenil(benzyl)-ksantynil-8-metyltioatsetatnykh kyslot ta yikh vodorozchynnykh solei [Synthesis and physicochemical properties of 3-phenyl(benzyl)xanthinyl-8-methylthioacetic acids and their water-soluble salts]. Aktualni pytannia farmatsevtychnoi ta medychnoi nauky i praktyky, 2, 45–48. [in Ukrainian].

[Elektronnij resurs]. Retrieved from http://www.chemicalize.org.

[Elektronnij resurs]. Retrieved from http://www.pharmaexpert.ru/Gusar/acutoxpredict.html.

Prijmenko, A. O., Vasil'ev, D. V., & Aleksandrova, E. V. (2013) Sintez, fiziko-himi4eskie i biologi4eskie svojstva nektoryh N7-zameschennyh 8-(gidroksimetil)-3-metil-3,7-digidro-1N-purin-2,6-diona [Synthesis physicochemical and biological properties of some N7-substituted 8-(hydroxymethyl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione]. Nauchnye vedomosti: Seriya Medicina, 4, 203–207. [in Russian].

Taran, A. V., Korniyenko, V. I., Samura, B. A. et al. (2010) Issledovanie diureticheskoj aktivnosti ammonievykh solej 7,8-dizameschennykh proizvodnykh 3-metilksantina [Research of diuretic activity of ammonium salts of 7,8-disubstituted 3-methylxanhtine derivatives]. Ukrainskyi biofarmatsevnychnyi zhurnal, 3, 14–17. [in Ukrainian].

Korniienko, V. I., Samura, B. A., Litarov, V. E., Nikolaev, V. A., Romanenko, N. I., Evseeva, L. V., & Ivanchenko, D.G. (2008) Issledovanie ostroj toksichnosti i diureticheskoj aktivnosti ammonijnykh solej 1,7-dizameschennykh 3-metilksantinil-8-tiouksusnoj kisloty [Research of acute toxicity and diuretic activity of ammonium salts of 1,7-disubstituted 3-methylxanthinyl-8-thioacetic acid]. Zaporozhskij medicinskij zhurnal, 5, 128–130. [in Ukrainian].

Downloads

How to Cite

1.
Mikhal’chenko EK, Аleksandrova KV, Levich SV. Synthesis and physical-chemical properties of 3-benzyl-8-propylxanthine and its water-soluble salts. Current issues in pharmacy and medicine: science and practice [Internet]. 2016Mar.9 [cited 2024Apr.26];(1). Available from: http://pharmed.zsmu.edu.ua/article/view/62005

Issue

No. 1 (2016)

Section

Synthesis of the biologically active compounds

License

Authors who publish with this journal agree to the following terms:

    1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.     Лицензия Creative Commons
    2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
    3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access)