Skip to main content
SpringerLink
Log in

Quadruple Bond Forming Multicomponent Approach to 5-(3-chromenyl)-5H-chromeno[2,3-b]pyridines and Its Interaction with the Neuropeptide Y1 Receptor

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Multicomponent reactions employ three or more reactants to obtain heterocycles containing fragments of all starting materials in a onepot process. All new bonds are formed at once, hence multicomponent reactions are characterized by high bond-forming index. A new multicomponent, one-pot reaction yielding previously unknown 5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-5H-chromeno[2,3-b]pyridines in 52–94% yield has been found. This multicomponent approach allows to construct four new bonds to synthesize some 5H-chromeno[2,3-b]-pyridines under mild conditions. Molecular docking and dynamics studies of the synthesized structures were carried out to identify their interaction with the binding pocket of the neuropeptide Y1 receptor.

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

Scheme 1.
Scheme 2.
Scheme 3.
Figure 1.
Figure 2.
Figure 3.
Figure 4.
Figure 5.
Figure 6.
Figure 7.

Similar content being viewed by others

References

  1. Rössner, S. Int. J. Obes. 2002, 26, S2.

    Article  Google Scholar 

  2. Ogden, C. L.; Carroll, M. D.; Kit, B. K.; Flegal, K. M. JAMA 2014, 311, 806.

    Article  CAS  Google Scholar 

  3. Holtcamp, W. Environ. Health Perspect. 2012, 120, a62.

    Article  Google Scholar 

  4. Garfinkel, L. Ann. Intern. Med. 1985, 103, 1034.

    Article  CAS  Google Scholar 

  5. Hammoud, A. O.; Gibson, M.; Peterson, C. M.; Meikle, A. W.; Carrell, D. T. Fertil. Steril. 2008, 90, 897.

    Article  Google Scholar 

  6. Sandmark, H.; Hogstedt, C.; Lewold, S.; Vingård, E. Ann. Rheum. Dis. 1999, 58, 151.

    Article  CAS  Google Scholar 

  7. Zhang, L.; Bijker, M. S.; Herzog, H. Pharmacol. Ther. 2011, 131, 91.

    Article  CAS  Google Scholar 

  8. Morales-Medina, J. C.; Dumont, Y.; Quirion, R. Brain Res. 2010, 1314, 194.

    Article  CAS  Google Scholar 

  9. Yulyaningsih, E.; Zhang, L.; Herzog, H.; Sainsbury, A. Br. J. Pharmacol. 2011, 163, 1170.

    Article  CAS  Google Scholar 

  10. Clarke, P. A.; Santos, S.; Martin, W. H. C. Green Chem. 2007, 9, 438.

    Article  CAS  Google Scholar 

  11. Newhouse, T.; Baran, P. S.; Hoffmann, R. W. Chem. Soc. Rev. 2009, 38, 3010.

    Article  CAS  Google Scholar 

  12. Hayashi, Y. Chem. Sci. 2016, 7, 866.

    Article  CAS  Google Scholar 

  13. Khasanov, A. F.; Kopchuk, D. S.; Kim, G. A.; Slepukhin, P. A.; Kovalev, I. S.; Santra, S.; Zyryanov, G. V.; Majee, A.; Chupakhin, O. N.; Charushin, V. N. ChemistrySelect 2018, 3, 340.

    Article  CAS  Google Scholar 

  14. Charushin, V. N.; Chupakhin, O. N. Russ. Chem. Bull., Int. Ed. 2019, 68, 453. [Izv. Akad. Nauk, Ser. Khim. 2019, 453.]

  15. Dömling, A.; Wang, K.; Wang, W. Chem Rev. 2012, 112, 3083.

    Article  Google Scholar 

  16. Tu, X.-J.; Fan, W.; Hao, W.-J.; Jiang, B.; Tu, S.-J. ACS Comb. Sci. 2014, 16, 647.

    Article  CAS  Google Scholar 

  17. Abdelmoniem, A. M.; Ghozlan, S. A. S.; Abdelmoniem, D. M.; Elwahy, A. H. M.; Abdelhamid, I. A. J. Heterocycl. Chem. 2017, 54, 2844.

    Article  CAS  Google Scholar 

  18. Bardasov, I. N.; Alekseeva, A. U.; Mihailov, D. L.; Ershov, O. V.; Grishanov, D. A. Tetrahedron Lett. 2015, 56, 1830.

    Article  CAS  Google Scholar 

  19. Zhang, W.; Wang, J.; Mao, J.; Hu, L.; Wu, X.; Guo, C. Tetrahedron Lett. 2016, 57, 1985.

    Article  CAS  Google Scholar 

  20. Olyaei, A.; Shahsavari, M. S.; Sadeghpour, M. Res. Chem. Intermed. 2018, 44, 943.

    Article  CAS  Google Scholar 

  21. Elinson, M. N.; Ryzhkov, F. V.; Nasybullin, R. F.; Vereshchagin, A. N.; Egorov, M. P. Helv. Chim. Acta 2016, 99, 724.

    Article  CAS  Google Scholar 

  22. Elinson, M. N.; Vereshchagin, A. N.; Ryzhkov, F. V.; Anisina, Y. E. ARKIVOC 2018, (iv), 276.

  23. Elinson, M. N.; Ryzhkov, F. V.; Korolev, V. A.; Egorov, M. P. Heterocycl. Commun. 2016, 22, 11.

    Article  CAS  Google Scholar 

  24. Vereshchagin, A. N.; Elinson, M. N.; Anisina, Y. E.; Ryzhkov, F. V.; Goloveshkin, A. S.; Bushmarinov, I. S.; Zlotin, S. G.; Egorov, M. P. Mendeleev Commun. 2015, 25, 424.

    Article  CAS  Google Scholar 

  25. Elinson, M. N.; Vereshchagin, A. N.; Anisina, Y. E.; Fakhrutdinov, A. N.; Goloveshkin, A. S.; Egorov, M. P. Eur. J. Org. Chem. 2019, 4171.

  26. Elinson, M. N.; Vereshchagin, A. N.; Anisina, Y. E.; Krymov, S. K.; Fakhrutdinov, A. N.; Egorov, M. P. Monatsh. Chem. 2019, 150, 1073.

    Article  CAS  Google Scholar 

  27. Elinson, M. N.; Vereshchagin, A. N.; Anisina, Y. E.; Krymov, S. K.; Fakhrutdinov, A. N.; Goloveshkin, A. S.; Egorov, M. P. Mol. Diversity 2020, 24, 617.

    Article  CAS  Google Scholar 

  28. Vereshchagin, A. N.; Elinson, M. N.; Anisina, Y. E.; Ryzhkov, F. V.; Novikov, R. A.; Egorov, M. P. ChemistrySelect 2017, 2, 4593.

    Article  CAS  Google Scholar 

  29. Vereshchagin, A. N.; Elinson, M. N.; Anisina, Y. E.; Ryzhkov, F. V.; Goloveshkin, A. S.; Novikov, R. A.; Egorov, M. P. J. Mol. Struct. 2017, 1146, 766.

    Article  CAS  Google Scholar 

  30. Elinson, M. N.; Nasybullin, R. F.; Ryzhkov, F. V; Egorov, M. P. C. R. Chim. 2014, 17, 437.

    Article  CAS  Google Scholar 

  31. Elinson, M. N.; Nasybullin, R. F.; Ryzhkov, F. V.; Zaimovskaya, T. A.; Nikishin, G. I. Monatsh. Chem. 2015, 146, 631.

    Article  CAS  Google Scholar 

  32. Elinson, M. N.; Vereshchagin, A. N.; Anisina, Y. E.; Krymov, S. K.; Fekhrutdinov, A. N.; Egorov, M. P. Mendeleev Commun. 2019, 29, 581.

    Article  CAS  Google Scholar 

  33. Elinson, M. N.; Vereshchagin, A. N.; Anisina, Y. E.; Krymov, S. K.; Fakhrutdinov, A. N.; Egorov, M. P. ARKIVOC 2019, (ii), 38.

  34. Elinson, M. N.; Vereshchagin, A. N.; Anisina, Y. E.; Goloveshkin, A. S.; Ushakov, I. E.; Egorov, M. P. Mendeleev Commun. 2018, 28, 372.

    Article  CAS  Google Scholar 

  35. Patai, S.; Israeli, Y. J. Chem. Soc. 1960, 2025.

  36. T.E.S.T., Version 4.2.; US EPA. 2016. https://www.epa.gov.edgekeystaging.net/chemical-research/toxicity-estimation-softwaretool- test; Accessed March 23, 2020.

  37. Martin, T. M.; Lilavois, C. R.; Barron, M. G. SAR QSAR Environ. Res. 2017, 28, 525.

    Article  CAS  Google Scholar 

  38. Calculation of Molecular Properties and Bioactivity, Molinspiration. http://www.molinspiration.com/; Accessed March 12, 2020.

  39. Rudolf, K.; Eberlein, W.; Engel, W.; Wieland, H. A.; Willim, K. D.; Entzeroth, M.; Wienen, W.; Beck-Sickinger, A. G.; Doods, H. N. Eur. J. Pharmacol. 1994, 271, R11.

    Article  CAS  Google Scholar 

  40. Stanley, B. G.; Kyrkouli, S. E.; Lampert, S.; Leibowitz, S. F. Peptides 1986, 7(6), 1189.

    Article  CAS  Google Scholar 

  41. LeadFinder 1.0; Biomoltech, 2011. https://www.cressetgroup.com/software/lead-finder/ and http://www.biomoltech.com/;Accessed March 12, 2020.

  42. Stroganov, O. V.; Novikov, F. N.; Stroylov, V. S.; Kulkov, V.; Chilov, G. G. J. Chem. Inf. Model. 2008, 48, 2371.

    Article  CAS  Google Scholar 

  43. Yang, Z.; Han, S.; Keller, M.; Kaiser, A.; Bender, B. J.; Bosse, M.; Burkert, K.; Kögler, L. M.; Wifling, D.; Bernhardt, G.; Plank, N.; Littmann, T.; Schmidt, P.; Yi, C.; Li, B.; Ye, S.; Zhang, R.; Xu, B.; Larhammar, D.; Stevens, R. C.; Huster, D.; Meiler, J.; Zhao, Q.; Beck-Sickinger, A. G.; Buschauer, A.; Wu, B. Nature 2018, 556, 520.

    Article  CAS  Google Scholar 

  44. The PyMOL Molecular Graphics System, Version 1.2r3pre; Schrödinger, LLC, 2019. https://pymol.org/; Accessed March 20, 2020.

  45. Lemkul, J. A. Living J. Comput. Mol. Sci. 2018, 1, 5068.

    Google Scholar 

  46. Vanommeslaeghe, K.; Hatcher, E.; Acharya, C.; Kundu, S.; Zhong, S.; Shim, J.; Darian, E.; Guvench, O.; Lopes, P.; Vorobyov, I.; Mackerell, A. D. J. Comput. Chem. 2010, 31, 671.

    CAS  PubMed  PubMed Central  Google Scholar 

  47. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991, Russia

    Fedor V. Ryzhkov, Yuliya E. Ryzhkova, Michail N. Elinson, Anatoly N. Vereshchagin, Victor A. Korolev & Mikhail P. Egorov

Authors
  1. Fedor V. Ryzhkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yuliya E. Ryzhkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Michail N. Elinson
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Anatoly N. Vereshchagin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Victor A. Korolev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Mikhail P. Egorov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Fedor V. Ryzhkov.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(12), 1560–1568

Supplementary Information

ESM 1

(PDF 1803 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ryzhkov, F.V., Ryzhkova, Y.E., Elinson, M.N. et al. Quadruple Bond Forming Multicomponent Approach to 5-(3-chromenyl)-5H-chromeno[2,3-b]pyridines and Its Interaction with the Neuropeptide Y1 Receptor. Chem Heterocycl Comp 56, 1560–1568 (2020). https://doi.org/10.1007/s10593-020-02850-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02850-x

Keywords

Search

Navigation