Skip to main content
SpringerLink
Log in

Synthesis of 1,3-Oxazine Derivatives Based on (–)-Isopulegol using the Ritter Reaction and Study of their Analgesic Activity

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The Ritter reaction between monoterpenoid (–)-isopulegol and nitriles in the presence of concentrated sulfuric acid or trifluoromethanesulfonic acid yielded a series of chiral 1,3-oxazine derivatives. When studying the analgesic activity of the synthesized compounds in vivo, it was found that 1,3-oxazine synthesized by the reaction of (–)-isopulegol with benzyl cyanide increases the time of latency of the animal in the hot plate test of thermal pain irritation, not inferior in effectiveness to the comparison drug diclofenac sodium.

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

Figure 1.
Figure 2.

Similar content being viewed by others

References

  1. Zinad, D. S.; Mahal, A.; Mohapatra, R. K.; Sarangi, A. K.; Pratama, M. R. F. Chem. Biol. Drug Des. 2020, 95, 16.

    Article  CAS  Google Scholar 

  2. Yakovlev, I. P.; Prep'yalov, A. V.; Ivin, B. A. Chem. Heterocycl. Compd. 1994, 30, 255. [Khim. Geterotsikl. Soedinen. 1994, 291.]

  3. a Verma, V.; Singh, K.; Kumar, D.; Klapötke, T. M.; Stierstorfer, J.; Narasimhan, B.; Qazi, A. K.; Hamid, A.; Jaglan, S. Eur. J. Med. Chem. 2012, 56, 195. (b) Thaler, F.; Varasi, M.; Abate, A.; Carenzi, G.; Colombo, A.; Bigogno, C.; Boggio, R.; Zuffo, R. D.; Rapetti, D.; Resconi, A.; Regalia, N.; Vultaggio, S.; Dondio, G.; Gagliardi, S.; Minucci, S.; Mercurio, C. Eur. J. Med. Chem. 2013, 64, 273.

  4. a Mathew, B. P.; Kumar, A.; Sharma, S.; Shukla, P. K.; Nath, M. Eur. J. Med. Chem. 2010, 45, 1502. (b) Kategaonkar, A. H.; Sonar, S. S.; Pokalwar, R. U.; Kategaonkar, A. H.; Shingate, B. B.; Shingare, M. S. Bull. Korean Chem. Soc. 2010, 31, 1657. (c) Mayekar, A. N.; Yathirajan, H. S.; Narayana, B.; Sarojini, B. K.; Suchetha Kumari, N.; Harrison, W. T. A. Int. J. Chem. 2011, 3, 74. (d) Didwagh, S. S.; Piste, P. B. Int. J. ChemTech Res. 2013, 5, 2199. (e) Abou-Elmagd, W. S. I.; Hashem, A. I. Med. Chem. Res. 2013, 22, 2005.

  5. (а) Pedersen, O. S.; Pedersen, E. B. Synthesis 2000, 479. a Cocuzza, A. J.; Chidester, D. R.; Cordova, B. C.; Jeffrey, S.; Parsons, R. L.; Bacheler, L. T.; Erickson-Viitanen, S.; Trainor, G. L.; Ko, S. S. Bioorg. Med. Chem. Lett. 2001, 11, 1177. b Gawali, R.; Trivedi, J.; Bhansali, S.; Bhosale, R.; Sarkar, D.; Mitra, D. Eur. J. Med. Chem. 2018, 157, 310.

  6. a Akhter, M.; Habibullah, S.; Hasan, S. M.; Alam, M. M.; Akhter, N.; Shaquiquzzaman, M. Med. Chem. Res. 2011, 20, 1147. (b) Zhang, H. J.; Li, Y. F.; Cao, Q. I.; Tian, Y. S.; Quan, Z. S. Pharmacol. Rep. 2017, 69, 419.

  7. Prostota, Y.; Berthet, J.; Delbaere, S.; Coelho, P. J. Dyes Pigm. 2013, 96, 569.

    Article  CAS  Google Scholar 

  8. (а) Mohammadpoor-Baltork, I.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Eskandari, Z. Ultrason. Sonochem. 2010, 17, 857. a El-Bayouki, K. A. M.; Basyouni, W. M.; Khatab, T. K.; Kandel, E. M.; Badawy, D. S.; Abdel-Galil, E.; El-Henawy, A. A. J. Heterocycl. Chem. 2016, 54, 1054.

  9. (а) Mollo, M. C.; Orelli, L. R. Org. Lett. 2016, 18, 6116. a Ranjith, J.; Rajesh, N.; Sridhar, B.; Radha Krishna, P. Org. Biomol. Chem. 2016, 14, 10074.

  10. Cwik, A.; Hell, Z.; Hegedüs, A.; Finta, Z.; Horváth, Z. Tetrahedron Lett. 2002, 43, 3985.

    Article  CAS  Google Scholar 

  11. Badiang, J. G.; Aubé, J. J. Org. Chem. 1996, 61, 2484.

    Article  CAS  Google Scholar 

  12. Murai, T.; Sano, H.; Kawai, H.; Aso, H.; Shibahara, F. J. Org. Chem. 2005, 70, 8148.

    Article  CAS  Google Scholar 

  13. Chen, G.; Fu, C.; Shengming, M. Org. Lett. 2009, 11, 2900.

    Article  CAS  Google Scholar 

  14. (a) Ohki, S.; Yoshino, M. Chem. Pharm. Bull. 1969, 17, 2142. (b) Couture, A.; Deniau, E.; Grandclaudon, P.; Vata, M. J. Chem. Res., Synop. 1998, 484.

  15. Ritter, J. J.; Kalish, J. J. Am. Chem. Soc. 1948, 70, 4048.

    Article  CAS  Google Scholar 

  16. Jiang, D.; He, T.; Ma, L.; Wang, Z. RSC Adv. 2014, 4, 64936.

    Article  CAS  Google Scholar 

  17. a Ilyina, I. V.; Zarubaev, V. V.; Lavrentieva, I. N.; Shtro, A. A.; Esaulkova, I. L.; Korchagina, D. V.; Borisevich, S. S.; Volcho, K. P.; Salakhutdinov, N. F. Bioorg. Med. Chem. Lett. 2018, 28, 2061. (b) Nazimova, E. V.; Shtro, A. A.; Anikin, V. B.; Patrusheva, O. S.; Il'ina, I. V.; Korchagina, D. V.; Zarubaev, V. V.; Volcho, K. P.; Salakhutdinov, N. F. Chem. Nat. Compd. 2017, 53, 260. [Khim. Prirod. Soedin. 2017, 222.]

  18. a Li-Zhulanov, N. S.; Zakharenko, A. L.; Chepanova, A. A.; Patel, J.; Zafar, A.; Volcho, K. P.; Salakhutdinov, N. F.; Reynisson, J.; Leung, I. K. H.; Lavrik, O. I. Molecules 2018, 23, 2468. (b) Chepanova, A. A.; Li-Zhulanov, N. S.; Sukhikh, A. S.; Zafar, A.; Reynisson, J.; Zakharenko, A. L.; Zakharova, O. D.; Korchagina, D. V.; Volcho, K. P.; Salakhutdinov, N. F.; Lavrik, O. I. Russ. J. Bioorg. Chem. 2019, 45, 647.

  19. a Nazimova, E.; Pavlova, A.; Mikhalchenko, O.; Il’ina, I.; Korchagina, D.; Tolstikova, T.; Volcho, K.; Salakhutdinov, N. Med. Chem. Res. 2016, 25, 1369. (b) Il'ina, I.; Morozova, E.; Korсhagina, D.; Volсho, K.; Tolstikova, T.; Salakhutdinov, N. Lett. Drug Des. Discovery 2020, 17, 68.

  20. Le, T. M.; Szilasi, T.; Volford, B.; Szekeres, A.; Fülöp, F.; Szakonyi, Z. Int. J. Mol. Sci. 2019, 20, 4050.

    Article  CAS  Google Scholar 

  21. Bernath, G.; Fulop, F.; Gera, L.; Hackler, L.; Kalman, A.; Argay, G.; Sohar, P. Tetrahedron 1979, 35, 799.

    Article  CAS  Google Scholar 

  22. (а) Il’ina, I.; Morozova, E.; Korсhagina, D.; Volсho, K.; Tolstikova, T.; Salakhutdinov, N. Lett. Drug Des. Discovery 2018, 17, 68. a Patrusheva, O. S.; Volcho, K. P.; Salakhutdinov, N. F. Russ. Chem. Rev. 2018, 87, 771. [Usp. Khim. 2018, 87, 771.]

  23. a Li-Zhulanov, N. S.; Il'ina, I. V.; Chicca, A.; Schenker, P.; Patrusheva, O. S.; Nazimova, E. V.; Korchagina, D. V.; Krasavin, M.; Volcho, K. P.; Salakhutdinov, N. F. Med. Chem. Res. 2019, 28, 450. (b) Pavlova, A.; Patrusheva, O.; Il'ina, I.; Volcho, K.; Tolstikova, T.; Salakhutdinov, N. Lett. Drug Des. Discovery 2017, 14, 508. (c) Slater, S.; Lasonkar, P. B.; Haider, S.; Alqahtani, M. J.; Chittiboyina, A. G.; Khan, I. A. Tetrahedron Lett. 2018, 59, 807.

  24. Eddy, N. B.; Leimbach, D. J. Pharmacol. Exp. Ther. 1953, 107, 385.

    CAS  PubMed  Google Scholar 

  25. a Mikhalchenko, O.; Il'ina, I.; Pavlova, A.; Morozova, E.; Korchagina, D.; Tolstikova, T.; Pokushalov, E.; Volcho, K.; Salakhutdinov, N. Med. Chem. Res. 2013, 22, 3026. (b) Kurbakova, S.; Il'ina, I.; Pavlova, A.; Korchagina, D.; Yarovaya, O.; Tolstikova, T.; Volcho, K.; Salakhutdinov, N. Med. Chem. Res. 2014, 23, 1709.

  26. (а) Harmer, M. A.; Junk, C.; Rostovtsev, V.; Carcani, L. G.; Vickery, J.; Schnepp, Z. Green Chem. 2007, 9, 30. a Kazakova, A. N.; Vasilyev, A. V. Russ. J. Org. Chem. 2017, 53, 485. [Zh. Org. Khim. 2017, 53, 479.]

  27. Michaudel, Q.; Thevenet, D.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 2547.

    Article  CAS  Google Scholar 

  28. Sheldrick, G. M. SADABS. Version 2.01; Bruker AXS Inc.: Madison, 2004.

  29. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, С71, 3.

Download references

Author information

Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russia

    Nikolai S. Li-Zhulanov, Alla V. Pavlova, Dina V. Korchagina, Yurii V. Gatilov, Konstantin P. Volcho, Tatyana G. Tolstikova & Nariman F. Salakhutdinov

  2. Novosibirsk State University, 2 Pirogova St, Novosibirsk, 630090, Russia

    Nikolai S. Li-Zhulanov, Konstantin P. Volcho & Nariman F. Salakhutdinov

Authors
  1. Nikolai S. Li-Zhulanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alla V. Pavlova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dina V. Korchagina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yurii V. Gatilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Konstantin P. Volcho
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tatyana G. Tolstikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Nariman F. Salakhutdinov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Konstantin P. Volcho.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 936–941

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li-Zhulanov, N.S., Pavlova, A.V., Korchagina, D.V. et al. Synthesis of 1,3-Oxazine Derivatives Based on (–)-Isopulegol using the Ritter Reaction and Study of their Analgesic Activity. Chem Heterocycl Comp 56, 936–941 (2020). https://doi.org/10.1007/s10593-020-02753-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02753-x

Keywords

Search

Navigation