Skip to main content
Log in

Synthesis of new conjugates of 6-thiopurine and thioguanine with (S)-glutamic acid

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

We have developed an efficient method for the synthesis of 6-thiopurine and thioguanine conjugates containing a (S)-glutamic acid residue, which is based on the reaction of 6-thio derivatives of purine with di-tert-butyl N-chloroacetyl-(S)-glutamate and subsequent hydrolysis of the ester groups.

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. J.-S. Yoon, D. B. Jarhad, G. Kim, A. Nayak, L. X. Zhao, J. Yu, H.-R. Kim, J. Y. Lee, V. A. Mulamoottil, G. Chandra, W. S. Byun, S. K. Lee, Y.-C. Kim, L. S. Jeong, Eur. J. Med. Chem., 2018, 155, 406; DOI: https://doi.org/10.1016/j.ejmech.2018.06.003.

    Article  CAS  Google Scholar 

  2. C. O. Salas, A. M. Zarate, V. Kryštof, J. Mella, M. Faundez, J. Brea, M. I. Loza, I. Brito, D. Hendrychová, R. Jorda, A. R. Cabrera, R. A. Tapia, C. Espinosa-Bustos, Int. J. Mol. Sci., 2020, 21, 161; DOI: https://doi.org/10.3390/ijms21010161.

    Article  CAS  Google Scholar 

  3. A. Kowalska, M. Latocha, K. Pluta, Med. Chem. Res., 2015, 24, 3107; DOI: https://doi.org/10.1007/s00044-015-1364-2.

    Article  CAS  Google Scholar 

  4. A. Kowalska, K. Pluta, M. Latocha, Med. Chem. Res., 2018, 27, 1384; DOI: https://doi.org/10.1007/s00044-018-2155-3.

    Article  CAS  Google Scholar 

  5. V. P. Krasnov, V. V. Musiyak, O. A. Vozdvizhenskaya, G. A. Galegov, V. L. Andronova, D. A. Gruzdev, E. N. Chulakov, A. Y. Vigorov, M. A. Ezhikova, M. I. Kodess, G. L. Levit, V. N. Charushin, Eur. J. Org. Chem., 2019, 4811; DOI: https://doi.org/10.1002/ejoc.201900727.

  6. O. A. Vozdvizhenskaya, V. L. Andronova, G. A. Galegov, G. L. Levit, V. P. Krasnov, V. N. Charushin, Chem. Heterocycl. Compd., 2021, 57, 490; DOI: https://doi.org/10.1007/s10593-021-02929-z.

    Article  CAS  Google Scholar 

  7. V. P. Krasnov, V. V. Zarubaev, D. A. Gruzdev, O. A. Vozdvizhenskaya, S. A. Vakarov, V. V. Musiyak, E. N. Chulakov, A. S. Volobueva, E. O. Sinegubova, M. A. Ezhikova, M. I. Kodess, G. L. Levit, V. N. Charushin, Chem. Heterocycl. Compd., 2021, 57, 498; DOI: https://doi.org/10.1007/s10593-021-02930-6.

    Article  CAS  Google Scholar 

  8. P. K. Sahu, T. Umme, J. Yu, A. Nayak, G. Kim, M. Noh, J.-Y. Lee, D.-D. Kim, L. S. Jeong, J. Med. Chem., 2015, 58, 8734; DOI: https://doi.org/10.1021/acs.jmedchem.5b00804.

    Article  CAS  Google Scholar 

  9. Y. Fu, D. Liu, H. Zeng, X. Ren, B. Song, D. Hu, X. Gan, RSC Adv., 2020, 10, 24483; DOI: https://doi.org/10.1039/D0RA03684F.

    Article  CAS  Google Scholar 

  10. D. A. Gruzdev, V. V. Musiyak, G. L. Levit, V. P. Krasnov, V. N. Charushin, Russ. Chem. Rev., 2018, 87, 604; DOI: https://doi.org/10.1070/RCR4772.

    Article  CAS  Google Scholar 

  11. V. P. Krasnov, G. L. Levit, V. V. Musiyak, D. A. Gruzdev, V. N. Charushin, Pure Appl. Chem., 2020, 92, 1277; DOI: https://doi.org/10.1515/pac-2019-1214.

    Article  CAS  Google Scholar 

  12. A. B. Bayoumy, F. Crouwel, N. Chanda, T. H. J. Florin, H. J. C. Buiter, C. J. J. Mulder, N. K. H. de Boer, Eur. J. Drug Metab. Pharmacokinet., 2021, 46, 743; DOI: https://doi.org/10.1007/s13318-021-00716-x.

    Article  CAS  Google Scholar 

  13. P. Karran, N. Attard, Nat. Rev. Cancer., 2008, 8, 24; DOI: https://doi.org/10.1038/nrc2292.

    Article  CAS  Google Scholar 

  14. K. Tominaga, T. Sugaya, T. Tanaka, M. Kanazawa, M. Iijima, A. Irisawa. Front. Pharmacol., 2021, 11, Art. 582291; DOI: https://doi.org/10.3389/fphar.2020.582291.

  15. E. V. Aleksandrova, P. M. Kochergin, Pharm. Chem. J., 2012, 46, 612; DOI: https://doi.org/10.1007/s11094-013-0856-y.

    Article  Google Scholar 

  16. E. S. Biberina, V. M. Nikol’skii, M. A. Feofanova, Russ. Chem. Bull., 2020, 69, 1916; DOI: https://doi.org/10.1007/s11172-020-2978-1.

    Article  CAS  Google Scholar 

  17. N. Harada, M. Hongu, T. Tanaka, T. Kashida, N. Narasaki, M. Ohohashi, K. Oda, T. Hashiyama, K. Tsujihara, Chem. Pharm. Bull., 1995, 43, 1793; DOI: https://doi.org/10.1248/cpb.43.1793.

    Article  CAS  Google Scholar 

  18. T. Kashida, N. Narasaki, A. Sakai, K. Tsujihara, K. Tsuzurahara, K. Naito, S. Takeyama, Immunopharmacology, 1997, 37, 95; DOI: https://doi.org/10.1016/s0162-3109(97)00039-8.

    Article  CAS  Google Scholar 

  19. V. P. Krasnov, A. Y. Vigorov, V. V. Musiyak, I. A. Nizova, D. A. Gruzdev, T. V. Matveeva, G. L. Levit, M. A. Kravchenko, S. N. Skornyakov, O. B. Bekker, V. N. Danilenko, V. N. Charushin, Bioorg. Med. Chem. Lett., 2016, 26, 2645; DOI: https://doi.org/10.1016/j.bmcl.2016.04.017.

    Article  CAS  Google Scholar 

  20. D. A. Gruzdev, E. N. Chulakov, G. L. Levit, M. A. Kravchenko, V. P. Krasnov, V. N. Charushin, Mendeleev Commun., 2017, 27, 547; DOI: https://doi.org/10.1016/j.mencom.2017.11.002.

    Article  CAS  Google Scholar 

  21. V. V. Musiyak, D. A. Gruzdev, M. A. Kravchenko, D. V. Vakhrusheva, G. L. Levit, V. P. Krasnov, V. N. Charushin, Mendeleev Commun., 2019, 29, 11; DOI: https://doi.org/10.1016/j.mencom.2019.01.002.

    Article  CAS  Google Scholar 

  22. V. P. Krasnov, A.Yu. Vigorov, E. N. Chulakov, I. A. Nizova, G. L. Levit, M. A. Kravchenko, V. N. Charushin, Russ. J. Org. Chem., 2019, 55, 755; DOI: https://doi.org/10.1134/S1070428019060034.

    Article  CAS  Google Scholar 

  23. V. V Musiyak, I. A. Nizova, T. V. Matveeva, G. L. Levit, V. P. Krasnov, V. N. Charushin, Russ. J. Org. Chem., 2019, 55, 762; DOI: https://doi.org/10.1134/S1070428019060046.

    Article  CAS  Google Scholar 

  24. M. Gangar, S. Goyal, D. Raykar, P. Khurana, A. M. Martis, A. Goswami, I. Ghoshal, K. V. Patel, Y. Nagare, S. Raikar, A. Mukherjee, R. Cyriac, J.-F. Paquin, A. Kulkarni. Bioorg. Chem., 2022, 119, Art. 105549; DOI: https://doi.org/10.1016/j.bioorg.2021.105549.

  25. J. Elguero, P. Goya, A. Martinez, I. Rozas, Chem. Ber., 1989, 122, 919; DOI: https://doi.org/10.1002/cber.19891220521.

    Article  CAS  Google Scholar 

  26. E. Rojas-Prats, L. Martinez-Gonzalez, C. Gonzalo-Consuegra, N. F. Liachko, C. Perez, D. Ramírez, B. C. Kraemer, A. Martin-Requero, D. I. Perez, C. Gil, E. de Lago, A. Martinez. Eur. J. Med. Chem., 2021, 210, Art. 112968; DOI: https://doi.org/10.1016/j.ejmech.2020.112968.

  27. K. G. Siver, K. B. Sloan, J. Pharm. Sci., 1990, 79, 66; DOI: https://doi.org/10.1002/jps.2600790116.

    Article  CAS  Google Scholar 

  28. E. Abele, K. Rubina, R. Abele, I. Sleiksha, E. Lukevics, Chem. Heterocycl. Compd., 1999, 35, 1052; DOI: https://doi.org/10.1007/BF02251796.

    Article  CAS  Google Scholar 

  29. R. P. Waranis, K. B. Sloan, J. Pharm. Sci., 1987, 76, 587; DOI: https://doi.org/10.1002/jps.2600760803.

    Article  CAS  Google Scholar 

  30. K. B. Sloan, M. Hashida, J. Alexander, N. Bodor, T. Higuchi, J. Pharm. Sci., 1983, 72, 372; DOI: https://doi.org/10.1002/jps.2600720413.

    Article  CAS  Google Scholar 

  31. B. F. Baker, K. Ramasamy, J. Kiely, Bioorg. Med. Chem. Lett., 1996, 6, 1647; DOI: https://doi.org/10.1016/0960-894X(96)00295-8.

    Article  CAS  Google Scholar 

  32. D. Lichtenberg, F. Bergmann, Z. Neiman, Isr. J. Chem., 1972, 10, 805; DOI: https://doi.org/10.1002/ijch.197200081.

    Article  CAS  Google Scholar 

  33. P. Ü. Civcir, J. Mol. Struct: THEOCHEM, 2001, 535, 121; DOI:10.1016/S0166-1280(00)00586-8.

    Article  CAS  Google Scholar 

  34. J. Leszczynski, J. Phys. Chem., 1993, 97, 3520; DOI: https://doi.org/10.1021/j100116a014.

    Article  CAS  Google Scholar 

  35. L. V. Tsalmane, M. Yu. Lidak, Khimiko-Farmatsevticheskii Zhurnal, 1989, 23, 1129 (in Russian)

    Google Scholar 

  36. L. V. Tsalmane, M. Yu. Lidak, ChemInform, 1990, 21, 201, DOI: https://doi.org/10.1002/chin.199016304.

    Article  Google Scholar 

  37. M. T. Hussain, N. H. Rama, K. M. Khan, Lett. Org. Chem., 2010, 7, 557; DOI: https://doi.org/10.2174/157017810793362217.

    Article  CAS  Google Scholar 

  38. N. Leygue, M. Enel, A. Diallo, B. Mestre-Voegtlé, C. Galaup, C. Picard, Eur. J. Org. Chem., 2019, 2899; DOI: https://doi.org/10.1002/ejoc.201900280.

  39. W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals, 7th ed., Butterworth-Heinemann, 2013.

  40. M. C. Thorpe, W. Coburn Jr., J. A. Montgomery, J. Magn. Reson., 1974, 15, 98; DOI: https://doi.org/10.1016/0022-2364(74)90179-6.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. A. Gruzdev.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 19-13-00231-P). Equipment of the Centre for Joint Use “Spectroscopy and Analysis of Organic Compounds” (CJU “SAOC”) at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch) was used.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Based on the materials of the VI North Caucasus Symposium on Organic Chemistry NCOCS-2022 (April 18–22, 2022, Stavropol, Russian Federation).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2426–2430, November, 2022.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Telegina, A.A., Gruzdev, D.A., Levit, G.L. et al. Synthesis of new conjugates of 6-thiopurine and thioguanine with (S)-glutamic acid. Russ Chem Bull 71, 2426–2430 (2022). https://doi.org/10.1007/s11172-022-3670-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-022-3670-4

Key words

Navigation