Synthesis and phosphonylation of 6-methyl-4-aryl-2-thio-1,2,3,4-tetrahydropyrimidine5-carboxylic acids ethyl esters

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A new series of 6-methyl-4-aryl-2-thio-1,2,3,4-tetrahydropyrimidine-5-carboxylic acids ethyl esters was synthesized. The reaction of the obtained esters with dimethyl 2-chloroethynylphosphonate leads to the selective formation of new ethyl 3-(dimethoxyphosphoryl)-5-aryl-7-methyl-5 H -thiazolo[3,2- a ]pyrimidine-6-carboxylates.

About the authors

N. A. Nosova

St. Petersburg State Technological Institute (Technical University)

A. S. Skrylkova

St. Petersburg State Technological Institute (Technical University)

D. M. Egorov

St. Petersburg State Technological Institute (Technical University)

Email: diavoly@mail.ru

References

  1. Bhat M.A., Al-Omar M.A., Naglah A.M., Al-Dhfyan A. // J. Chem. 2020. Vol. 2020. P. 1. doi: 10.1155/2020/4284628
  2. Khaldi-Khellafi N., Makhloufi-Chebli M., Oukacha-Hikem D., Bouaziz S.T., Lamara K.O., Idir T., Benazzouz-Touami A., Dumas F. // J. Mol. Struct. 2019. Vol. 1181. P. 261. doi: 10.1016/j.molstruc.2018.12.104
  3. Bhat M.A., Al-Omar M.A., Khan A.A., Alanazi A.M., Naglah A.M. // Drug Design Dev. Ther. 2019. Vol. 2019. N 13. P. 2393. doi: 10.2147/DDDT.S198865
  4. Krishna B., Payra S., Roy S. // J. Colloid Interface Sci. 2022. Vol. 607. P.729. doi: 10.1016/j.jcis.2021.09.031
  5. Bhat M.A., Al-Omar M.A., Ghabbour H.A., Naglah A.M. // Molecule. 2018. Vol. 23. P. 1559. doi: 10.3390/molecules23071559
  6. Mathapati S.R., Prasad D., Atar A.B., Nagaraja B.M., Dawle J.K., Jadhav A.H. // Mater. Today Proceed. 2019. Vol. 9. P. 661. doi: 10.1016/j.matpr.2018.10.390
  7. Kazemi M. // Synth. Commun. 2020. Vol. 50. N 10. P. 1409. doi: 10.1080/00397911.2020.1720740
  8. Dowarah J., Patel D., Marak B.N., Yadav U.C.S., Shah P.K., Shukla P.K., Singh V.P. // RSC Adv. 2021. Vol. 11. P. 35747. doi: 10.1039/d1ra03969e
  9. Ilyas U., Nazir B., Altaf R., Muhammad S.A., Zafar H., Paiva-Santos A.C., Abbas M., Duan Y. // Front. Endocrin. 2022. Vol. 13. P. 1. doi: 10.3389/fendo.2022.1022623
  10. Matos L.H.S., Masson F.T., Simeoni L.A., Homem-de-Mello M. // Eur. J. Med. Chem. 2018. Vol. 143. P. 1779. doi: 10.1016/j.ejmech.2017.10.073
  11. Marinescu M. // Molecule. 2021. Vol. 26. P. 6022. doi: 10.3390/molecules26196022
  12. Shipilovskikh S.A., Rubtsov A.E. // J. Org. Chem. 2019. Vol. 84. N 24. P. 15788. doi: 10.1021/acs.joc.9b00711
  13. Maliga Z., Kapoor T.M., Mitchison T.J. // Chem. Biol. 2002. Vol. 9. N 9. P. 989. doi: 10.1016/S1074-5521(02)00212-0
  14. Sun X., Shi X., Sun X., Luo Y., Wu X., Yao C., Yu H., Li D., Liu M., Zhou J. // Acta Pharmacol. Sinica. 2011. Vol. 32. N 12. P. 1543. doi: 10.1038/aps.2011.130
  15. Bourne C.R., Finn M.G., Zlotnick A. // J. Virol. 2006. Vol. 80. N 22 P. 11055. doi: 10.1128/JVI.00933-06
  16. Atwal K.S., Swanson B.N., Unger S.E., Floyd D.M., Moreland S., Hedberg A., O'Reilly B.C. // J. Med. Chem. 1991. Vol. 34. N 2. P. 806. doi: 10.1021/jm00106a048
  17. Siutkina A.I., Chashchina S.V., Kizimova I.A., Igidov N.M., Makhmudov R.R., Shipilovskikh S.A. // Russ. J. Org. Chem. 2021. Vol. 57. N 11. P. 1874. doi: 10.1134/S1070428021110105
  18. Mourad A.K., Mohammed F.K., Tammam G.H., Mohammed S.R. // J. Heterocycl. Chem. 2019. Vol. 56. N 8. P. 2262. doi: 10.1002/jhet.3621
  19. Singh K., Singh K., Trappanese D.M., Moreland R.S. // Eur. J. Med. Chem. 2012. Vol. 54. P. 397. doi: 10.1016/j.ejmech.2012.05.017
  20. Essid I., Touil S. // Arkivoc. 2013. Vol. 4. P. 98. doi: 10.3998/ark.5550190.p007.871
  21. Essid I., Lahbib K., Kaminsky W., Nasr C.B., Touil S. // J. Mol. Struct. 2017. Vol. 1142. P. 130. doi: 10.1016/j.molstruc.2017.04.054
  22. Kaskevich K.I., Babushkina A.A., Gurzhiy V.V., Egorov D.M., Svintsitskaya N.I., Dogadina A.V. // Beilstein J. Org. Chem. 2020. Vol. 16. P. 1947. doi: 10.3762/bjoc.16.161
  23. Babushkina A.A., Dogadina A.V., Egorov D.M., Piterskaia J.L., Shtro A.A., Nikolaeva Y.V., Galochkina A.V., Kornev A.A., Boitsov V.M. // Med. Chem. Res. 2021. Vol. 30. N 12. P. 2203. doi: 10.1007/s00044-021-02801-x
  24. Егоров Д.М., Бабушкина А.А., Леоненок В.Е., Чекалов А.П., Питерская Ю.Л. // ЖОХ. 2020. Т. 90. № 2. С. 326.
  25. Egorov D.M., Babushkina A.A., Leonenok V.E., Chekalov A.P., Piterskaya Yu.L. // Russ. J. Gen. Chem. 2020. Vol. 90. N 2. P. 319. doi: 10.1134/S1070363220020267

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences