Skip to main content

Advertisement

SpringerLink
Log in

Synthesis and properties of substituted oxo- and thioxohexahydropyrimidine-5-carboxylic acids

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

Abstract

The regularities of the lactone ring opening in hexahydro-2H-chromeno[4,3-d]pyrim-idine-2,5-diones and thioxohexahydro-5H-chromeno[4,3-d]pyrimidines with bases to form the corresponding acids with retention of the initial configuration of diastereomers were studied. The resulting oxo- and thioxohexahydropyrimidine-5-carboxylic acids were found to possess the effect of “chemical memory”, namely, the tendency to lactonization into the original diastereomers of chromanes during acylation and methylation reactions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. S. S. Shatokhin, V. A. Tuskaev, S. Ch. Gagieva, E. T. Oganesyan, Russ. Chem. Bull., 2021, 70, 1011; DOI: https://doi.org/10.1007/s11172-021-3183-6.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. L. Liu, Y. Chen, R. F. Zeng, Y. Liu, S. S. Xie, J. S. Lan, Y. Ding, Y. T. Yang, J. Yang, T. Zhang, Bioorg. Chem., 2021, 109, 104685; DOI: https://doi.org/10.1016/j.bioorg.2021.104685.

    Article  CAS  PubMed  Google Scholar 

  3. G. Chen, N. Tokunaga, T. Hayashi, Org. Lett., 2005, 7, 2285; DOI: https://doi.org/10.1021/ol0507367.

    Article  CAS  PubMed  Google Scholar 

  4. F. Song, S. Lu, J. Gunnet, J. Z. Xu, P. Wines, J. Proost, Y. Liang, Ch. Baumann, J. Lenhard, W. V. Murray, K. T. Demarest, G. H. Kuo, J. Med. Chem., 2007, 50, 2807; DOI: https://doi.org/10.1021/jm070130j.

    Article  CAS  PubMed  Google Scholar 

  5. N. Madala, V. R. Ghanta, S. Vinnakota, N. Mendu, A. B. Ingle, K. Ethiraj, V. Sharma, Tetrahedron Lett., 2018, 59, 2708; DOI: https://doi.org/10.1016/j.tetlet.2018.05.090.

    Article  CAS  Google Scholar 

  6. R. P. Burman, Sh. Gupta, J. Bhatti, K. Verma, D. Rajak, M. S. Gill, Nat. Prod. Res., 2019, 33, 1147; DOI: https://doi.org/10.1080/14786419.2018.1460837.

    Article  CAS  PubMed  Google Scholar 

  7. P. Fu, M. Johnson, H. Chen, B. A. Posner, J. B. MacMillan, J. Nat. Prod., 2014, 77, 1245; DOI: https://doi.org/10.1021/np500207p.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. D. B. Chandrasekhar, S. C. Tsay, T. K. Pradhan, J. R. Hwu, J. Org. Chem., 2017, 82, 5524; DOI: https://doi.org/10.1021/acs.joc.7b00260.

    Article  CAS  PubMed  Google Scholar 

  9. D. Tian, R. Xu, J. Zhu, J. Huang, W. Dong, J. Claverie, W. Tang, Angew. Chem., Int. Ed., 2021, 60, 6305; DOI: https://doi.org/10.1002/anie.202015450.

    Article  CAS  Google Scholar 

  10. E. J. Carlson, A. M. S. Riel, B. J. Dahl, Tetrahedron Lett., 2012, 53, 6245; DOI: https://doi.org/10.1016/j.tetlet.2012.09.016.

    Article  CAS  Google Scholar 

  11. M. Prabhakar, G. N. Reddy, G. Srinu, K. Manjulatha, J. V. Prasad, S. P. Kumar, O. Srinivas, J. Iqbal, K. A. Kumar, Synlett, 2010, 6, 947; DOI: https://doi.org/10.1055/s-0029-1219532.

    Google Scholar 

  12. M. Löffler, E. A. Carrey, E. Zameitat, J. Genet. Genomics, 2015, 42, 207; DOI: https://doi.org/10.1016/j.jgg.2015.04.001.

    Article  PubMed  Google Scholar 

  13. Ya. V. Burgart, O. G. Kuzueva, M. V. Pryadeina, C. O. Kappe, V. I. Saloutin, Russ. J. Org. Chem., 2001, 37, 869; DOI: https://doi.org/10.1023/A:1012473901354.

    Article  CAS  Google Scholar 

  14. M. H. El-Hamamsy, N. A. Sharafeldin, T. F. El-Moselhy, H. O. Tawfik, Arch. Pharm., 2020, 353, 2000060; DOI: https://doi.org/10.1002/ardp.202000060.

    Article  CAS  Google Scholar 

  15. J. C. Bussolari, P. A. McDonnell, J. Org. Chem., 2000, 65, 6777; DOI: https://doi.org/10.1021/jo005512a.

    Article  CAS  PubMed  Google Scholar 

  16. Z. Fang, Y. Lam, Tetrahedron, 2011, 67, 1294; DOI: https://doi.org/10.1016/j.tet.2010.11.075.

    Article  CAS  Google Scholar 

  17. V. Kambappa, C. Ganganahalli Kotturappa, R. Sheshachar Manjunath, P. Doddakunche Shivaramu, J. Heterocycl. Chem., 2020, 57, 3475; DOI: https://doi.org/10.1002/jhet.4066.

    CAS  Google Scholar 

  18. K. Malani, S. S. Thakkar, M. C. Thakur, A. Ray, H. Doshi, Bioorg. Chem., 2016, 68, 265; DOI: https://doi.org/10.1016/j.bioorg.2016.09.001.

    Article  CAS  PubMed  Google Scholar 

  19. B. Desai, D. Dallinger, C. O. Kappe, Tetrahedron, 2006, 62, 4651; DOI: https://doi.org/10.1016/j.tet.2005.12.061.

    Article  CAS  Google Scholar 

  20. S. I. Filimonov, Zh. V. Chirkova, M. V. Kabanova, E. S. Makarova, A. A. Shetnev, V. A. Panova, K. Yu. Suponitsky, ChemistrySelect, 2019, 4, 9550; DOI: https://doi.org/10.1002/slct.201901997.

    Article  CAS  Google Scholar 

  21. E. S. Makarova, M. V. Kabanova, S. I. Filimonov, A. A. Shetnev, K. Yu. Suponitsky, Russ. Chem. Bull., 2022, 71, 1034; DOI: https://doi.org/10.1007/s11172-022-3505-3.

    Article  CAS  Google Scholar 

  22. E. S. Makarova, M. V. Kabanova, A. S. Danilova, S. I. Filimonov, E. A. Smirnova, A. A. Shetnev, Russ. Chem. Bull., 2021, 70, 1377; DOI: https://doi.org/10.1007/s11172-021-3226-z.

    Article  CAS  Google Scholar 

  23. I. A. Novakov, D. S. Sheikin, V. V. Chapurkin, M. B. Nawrozkij, B. D. Korenkov, I. A. Kirillov, P. P. Deshevov, O. V. Vostrikova, L. L. Brunilina, Russ. Chem. Bull., 2021, 70, 943; DOI: https://doi.org/10.1007/s11172-021-3171-x.

    Article  CAS  Google Scholar 

  24. I. A. Novakov, D. S. Sheikin, E. A. Ruchko, L. L. Brunilina, A. A. Vernigora, N. A. Salykin, O. V. Vostrikova, V. V. Chapurkin, M. B. Navrotsky, D. V. Kurkin, D. A. Bakulin, M. Yu. Vorontsov, L. A. Sablina, N. S. Kovalev, I. N. Tyurenkov, Russ. Chem. Bull., 2021, 70, 2220; DOI: https://doi.org/10.1007/s11172-021-3336-7.

    Article  CAS  Google Scholar 

  25. I. A. Novakov, D. S. Sheikin, V. V. Chapurkin, M. B. Nawrozkij, I. A. Kirillov, E. A. Ruchko, Russ. Chem. Bull., 2020, 69, 2363; DOI: https://doi.org/10.1007/s11172-020-3029-7.

    Article  CAS  Google Scholar 

  26. S. K. Sartori, M. A. N. Diaz, G. Diaz-Munoz, Tetrahedron, 2021, 84, 132001; DOI: https://doi.org/10.1016/j.tet.2021.132001.

    Article  CAS  Google Scholar 

  27. APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA, 2014.

  28. G. M. Sheldrick, Acta Crystallogr., 2015, C71, 3.

    Google Scholar 

Download references

Funding

This work was financially supported by the Russian Science Foundation (Project No. 22-13-20085).

X-ray diffraction studies were carried out within the framework of the Russian state assignment No. 075-00697-22-01 of the Ministry of Science and Higher Education of the Russian Federation.

Author information

Authors and Affiliations

  1. Yaroslavl State Technical University, 88 Moskovskii prosp., 150023, Yaroslavl, Russia

    E. S. Makarova, M. V. Kabanova, S. I. Filimonov & Zh. V. Chirkova

  2. Center of Transfer of Pharmaceutical Technologies, K. D. Ushinsky Yaroslavl State Pedagogical University, 108/1 ul. Respublikanskaya, 150000, Yaroslavl, Russia

    A. A. Shetnev

  3. G. V. Plekhanov Russian University of Economics, 36 Stremyannoy per., 117997, Moscow, Russia

    K. Yu. Suponitsky

  4. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russia

    K. Yu. Suponitsky

Authors
  1. E. S. Makarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Kabanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. I. Filimonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zh. V. Chirkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Shetnev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. K. Yu. Suponitsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to S. I. Filimonov, A. A. Shetnev or K. Yu. Suponitsky.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2255–2262, October, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Makarova, E.S., Kabanova, M.V., Filimonov, S.I. et al. Synthesis and properties of substituted oxo- and thioxohexahydropyrimidine-5-carboxylic acids. Russ Chem Bull 71, 2255–2262 (2022). https://doi.org/10.1007/s11172-022-3653-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-022-3653-5

Key words

Search

Navigation