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Synthesis and Properties of a Water-Soluble Ureide Derived from Gаlodif and Succinic Acid

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Abstract

A new ureide has been synthesized by acylation of the anticonvulsant and anti-alcohol drug galodif N-[(3-chlorophenyl)(phenyl)methyl]urea with succinic anhydride in the presence of some acids. Unlike galodif which is almost insoluble in water, the synthesized ureide is soluble in aqueous media. It is expected to exhibit higher bioavailability and is promising as a liquid drug dosage form and a prodrug with prolonged action.

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CONFLICT OF INTEREST

The authors declare the absence of conflict of interest.

REFERENCES

  1. Shushpanova, T.V., Bokhan, N.A., Stankevich, K.S., Novo­zheeva, T.P., Mandel’, A.I., Schastnyi, E.D., Shushpanova, O.V., Udut, V.V., Safronov, S.M., Boev, R.S., and Knyazeva, E.M., Pharm. Chem. J., 2021, vol. 54, p. 1093. https://doi.org/10.1007/s11094-021-02327-x

    Article  CAS  Google Scholar 

  2. Kuksenok, V.Yu., Shtrykova, V.V., Filimonov, V.D., Druganov, A.G., Bondarev, A.A., and Stankevich, K.S., Chirality, 2018, vol. 30, p. 1135. https://doi.org/10.1002/chir.23005

    Article  CAS  PubMed  Google Scholar 

  3. Shushpanova, T.V., Bokhan, N.A., Kuksenok, V.Yu., Shtrykova, V.V., Shushpanova, O.V., and Udut, V.V., Mendeleev Commun., 2023, vol. 33, p. 546. https://doi.org/10.1016/j.mencom.2023.06.034

    Article  CAS  Google Scholar 

  4. Silva, F.L.O.D., Marques, M.B.D.F., Kato, K.C., and Carneiro, G., Expert Opin. Drug Discovery, 2020, vol. 15, p. 853. https://doi.org/10.1080/17460441.2020.1750591

    Article  CAS  Google Scholar 

  5. Gupta, D.S., Parab, S.B., and Kaur, G., Curr. Res. Pharmacol. Drug Discovery, 2022, vol. 3, p. 100. https://doi.org/10.1016/j.crphar.2022.100121

    Article  Google Scholar 

  6. Volchegorskii, I.A., Izarovskii, B.V., Shamaeva, T.N., and Izarovskaia, I.V., Zh. Nevrolog. Psikhiatr. im. S.S. Korsakova, 2021, vol. 121, p. 63. https://doi.org/10.17116/jnevro202112109163

    Article  CAS  Google Scholar 

  7. Yue, W., Liu, Y.X., Zang, D. L., Zhou, M., Zhang, F., and Wang, L., Acta Pharmacol. Sin., 2002, vol. 23, p. 847. PMID: 12230956

    PubMed  Google Scholar 

  8. Ghosh, A.K. and Brindisi, M., J. Med. Chem., 2020, vol. 63, p. 2751. https://doi.org/10.1021/acs.jmedchem.9b01541

    Article  CAS  PubMed  Google Scholar 

  9. Xu, M., Jupp, A.R., Ong, M.S.E., Burton, K.I., Chitnis, S.S., and Stephan, D.W., Angew. Chem., Int. Ed., 2019, vol. 58, p. 5707. https://doi.org/10.1002/anie.201900058

    Article  CAS  Google Scholar 

  10. Vafina, G.F., Khanova, M.D., and Lobov, A.N., Chem. Nat. Compd., 2022, vol. 58, p. 1055. https://doi.org/10.1007/s10600-022-03865-w

    Article  CAS  Google Scholar 

  11. Bakibaev, A.A., Gorshkova, V.K., Tignibidina, L.G., Shtrykova, V.V., Filimonov, V.D., and Saratikov, A.S., Pharm. Chem. J., 1994, vol. 28, p. 452. https://doi.org/10.1007/BF02219245

    Article  Google Scholar 

  12. Manoni, F., Cornaggia, C., Murray, J., Tallon, S., and Connon, S.J., Chem. Commun., 2012, vol. 48, p. 6502. https://doi.org/10.1039/C2CC32147E

    Article  CAS  Google Scholar 

  13. Palani, A., Badea, V., Gerasimou, E., Nitu, S., Csunderlik, C., and Simon, M., Rev. Chim., 2011. vol. 62, p. 614.

    CAS  Google Scholar 

  14. Manda, P., Popescu, C., Juluri, A., Janga, K., Kakulamarri, P.R., Narishetty, S., Murthy, S.N., and Repka, M.A., AAPS PharmSciTech, 2018, vol. 19, p. 1358. https://doi.org/10.1208/s12249-017-0924-9

    Article  CAS  PubMed  Google Scholar 

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Funding

This study was performed in the framework of state assignment of the Ministry of Science and Higher Education of the Russian Federation (project no. FSWW-2020-011).

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Correspondence to V. Yu. Kuksenok.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 9, pp. 1228–1232 https://doi.org/10.31857/S0514749223090136.

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Kuksenok, V.Y., Cui, Y., Shtrykova, V.V. et al. Synthesis and Properties of a Water-Soluble Ureide Derived from Gаlodif and Succinic Acid. Russ J Org Chem 59, 1629–1632 (2023). https://doi.org/10.1134/S1070428023090221

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  • DOI: https://doi.org/10.1134/S1070428023090221

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