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Synthesis and Functionalization of 5-Alkyl-6-methyl-2-thiouracils

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Abstract

A number of 5-alkyl-6-methyl-2-thiouracils were obtained, the further introduction of which into the reaction with dialkyl chloroethynylphosphonates afforded a series of new dialkyl (6-alkyl-5-oxo-7-methyl-5H-thiazolo[3,2-a]pyrimidin- 3-yl)phosphonates.

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REFERENCES

  1. Briel, D., Holzer, M., Leistner, S., Droessler, K., and Dobner, B., Pharmazie, 2003, vol. 58, p. 759.

    CAS  PubMed  Google Scholar 

  2. Husz, H., Berko, D., and Kenderessy, S., Dermatol. Monatschr., 1979, vol. 165, p. 569.

    CAS  Google Scholar 

  3. Shin, N., Li, Y.-L., Mei, S., Wang, K.H., Hall, L., Katiyar, K., Wang, Q., Yang, G., Rumberger, B., Leffet, L., He, X., Rupar, M., Bowman, K., Favata, M., Li, J., Liu, M., Li, Y., Covington, M., Koblish, H., Soloviev, M., Shuey, D., Burn, T., Diamond, S., Fridman, J., Combs, A., Yao, W., Yeleswaram, S., Hollis, G., Vaddi, K., Huber, R., Newton, R., and Scherle, P.J., Pharmacol. Exp. Ther., 2018, vol. 364, p. 120. https://doi.org/10.1124/jpet.117.244947

    Article  CAS  Google Scholar 

  4. Abdo, N.Y.M., Acta Chim. Slov., 2015, vol. 62, p. 168. https://doi.org/10.17344/acsi.2014.867

    Article  CAS  Google Scholar 

  5. Verma, A., Sahu, L., Chaudhary, N., Dutta, T., Dewangan, D., and Tripathi, D.K., Asian J. Biochem. Pharm. Res., 2012, vol. 2, p. 1.

    CAS  Google Scholar 

  6. Khobragade, C.N., Bodade, R.G., Konda, S.G., Dawane, B.S., and Manwar, A.V., Eur. J. Med. Chem., 2010, vol. 45, p. 1635. https://doi.org/10.1016/j.ejmech.2009.12.040

    Article  CAS  PubMed  Google Scholar 

  7. Mohamed, M.M., Khalil, A.K., Abbass, E.M., and El Naggar, A.M., Synth. Commun., 2017, vol. 47, p. 1441. https://doi.org/10.1080/00397911.2017.1332223

    Article  CAS  Google Scholar 

  8. Velnati, S., Massarotti, A., Antona, A., Talmon, M., Fresu, L.G., Galetto, A.S., and Baldanzi, G., J. Enzyme. Inhib. Med. Chem., 2019, vol. 35, p. 96. https://doi.org/10.1080/14756366.2019.1684911

    Article  CAS  PubMed Central  Google Scholar 

  9. Hazari, P.P., Pandey, A., Chaturvedi, S., and Mishra, A.K., Bioconjug. Chem., 2017, vol. 28, p. 2647. https://doi.org/10.1021/acs.bioconjchem.7b00243

    Article  CAS  PubMed  Google Scholar 

  10. Abdel Moty, S.G., Hussein, M.A., Abdel Aziz, S.A., and Abou-Salim, M.A., Saudi Pharm. J., 2016, vol. 24, p. 119. https://doi.org/10.1016/j.jsps.2013.12.016

    Article  PubMed  Google Scholar 

  11. Nagarajaiah, H., Khazi, I.M., and Begum, N.S., J. Chem. Sci., 2012, vol. 124, p. 847. https://doi.org/10.1007/s12039-012-0271-z

    Article  CAS  Google Scholar 

  12. Mobinikhaledi, A., Foroughifar, N., and Ahmadi, B., Phosphorus, Sulfur, Silicon, Relat. Elem., 2005, vol. 180, p. 339. https://doi.org/10.1080/104265090508406

    Article  CAS  Google Scholar 

  13. Xiao, D., Han, L., Sun, Q., Chen, Q., Gong, N., Lv, Y., and Li, R., RSC Adv., 2012, vol. 2, p. 5054. https://doi.org/10.1039/c2ra20254a

    Article  CAS  Google Scholar 

  14. Piechowicz, K.A., Truong, E.C., Javed, K.M., Chaney, R.R., Wu, J.Y., Phuan, P.W., and Anderson, M.O., J. Enzyme Inhib. Med. Chem., 2016, vol. 31, p. 1362. https://doi.org/10.3109/14756366.2015.1135912

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Khudina, O.G., Ivanova, A.E., Burgart, Y.V., Pervova, M.G., Shatunova, T.V., Borisevich, S.S., and Saloutin, V.I., Russ. J. Org. Chem., 2019, vol. 55, p. 782. https://doi.org/10.1134/s1070428019060071

    Article  CAS  Google Scholar 

  16. Giuliano, B.M., Feyer, V., Prince, K.C., Coreno, M., Evangelisti, L., Melandri, S., and Caminati, W., J. Phys. Chem. (A), 2010, vol. 114, p. 12725. https://doi.org/10.1021/jp106883s

    Article  CAS  Google Scholar 

  17. Khvorostov, A., Lapinski, L., Rostkowska, H., and Nowak, M.J., J. Phys. Chem. (A), 2005, vol. 109, p. 7700. https://doi.org/10.1021/jp051940e

    Article  CAS  Google Scholar 

  18. Yekeler, H., J. Comput. Aid. Mol. Design., 2000, vol. 14, p. 243. https://doi.org/10.1023/a:1008132202838

    Article  CAS  Google Scholar 

  19. Egorov, D.M., Piterskaya, Y.L., Dogadina, A.V., and Svintsitskaya, N.I., Tetrahedron Lett., 2015, vol. 56, p. 1552. https://doi.org/10.1016/j.tetlet.2015.02.027

    Article  CAS  Google Scholar 

  20. Egorov, D.M., Babushkina, A.A., Leonenok, V.E., Chekalov, A.P., and Piterskaya, Y.L., Russ. J. Gen. Chem., 2020, vol. 90, p. 319. https://doi.org/10.1134/s1070363220020267

    Article  CAS  Google Scholar 

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Funding

This work was supported by the Russian Foundation for Basic Research (grant no. 19-03-00365) within the basic part of the governmental task of the Ministry of Science and Higher Education (no. 785.00.X6019) using the equipment of the Engineering Center of the St. Petersburg State Institute of Technology.

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Correspondence to D. M. Egorov.

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Babushkina, A.A., Egorov, D.M. & Kaskevich, K.I. Synthesis and Functionalization of 5-Alkyl-6-methyl-2-thiouracils. Russ J Gen Chem 90, 2093–2097 (2020). https://doi.org/10.1134/S1070363220110110

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  • DOI: https://doi.org/10.1134/S1070363220110110

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