Skip to main content
SpringerLink
Log in

Application of the Benzoyl O-Protecting Group in the Synthesis of α,β-Dehydrotyrosine-containing Amides and Imidazolones

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The use of O-benzoyl protection in the synthesis of N-benzoyl-α,β-dehydrotyrosine benzylamide, and the corresponding 4-imidazolone was studied. The reaction of 4-(4-benzoyloxybenzylidene)oxazol-5(4H)-one with benzylamine proceeds with the retention of the O-benzoyl protecting group. The latter is removed with 2-(dimethylamino)-1-ethylamine or 3-(dimethylamino)-1-propylamine. In the case of the cyclization of N,O-dibenzoyl-α,β-dehydrotyrosine benzylamide with 1,1,1,3,3,3-hexamethyldisilazane into (Z)-3-benzyl-5-(4-hydroxybenzylidene)-2-phenyl-3,5-dihydro-4H-imidazol-4-one leads to elimination of the O-benzoyl protection. The antiradical and anticholinesterase properties of the synthesized compounds were studied.

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
Fig. 1.
Fig. 2.

Similar content being viewed by others

REFERENCES

  1. Saito, R., Hoshi, M., Kato, A., Ishikawa, C., and Komatsu, T., Eur. J. Med. Chem., 2017, vol. 125, p. 965. https://doi.org/10.1016/j.ejmech.2016.10.016

    Article  CAS  PubMed  Google Scholar 

  2. Lee, C.-Y., Chen, Y.-C., Lin, H.-C., Jhong, Y., Chang, C.-W., Tsai, C.-H., Kao, C.-L., and Chien, T.C., Tetrahedron, 2012, vol. 68, p. 5898. https://doi.org/10.1016/j.tet.2012.04.102

    Article  CAS  Google Scholar 

  3. He, X., Bell, A.F., and Tong, P., J. Org. Lett., 2002, vol. 4, p. 1523. https://doi.org/10.1021/o10200403

    Article  CAS  Google Scholar 

  4. Kojima, S., Ohkawa, H., Hirano, T., Maki, S., Niwa, H., Ohashi, M., Inouye, S., and Tsuji, F.I., Tetrahedron Lett., 1998, vol. 39, p. 5239. https://doi.org/10.1016/S0040-4039(98)01031-4

    Article  CAS  Google Scholar 

  5. Bell, A.F., He, X., Wachter, R.M., and Tonge, P.J., Biochemistry, 2000, vol. 39, p. 4423. https://doi.org/10.1021/bi992675o

    Article  CAS  PubMed  Google Scholar 

  6. Niwa, H., Inouye, S., Hirano, T., Matsuno, T., Kojima, S., Kubota, M., Ohashi, M., and Tsuji, F., PNAS, 1996, vol. 93, p. 13617. https://doi.org/10.1073/pnas.93.24.13617

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Chuang, W.-T., Hsieh, C.-C., Lai, C.-H., Lai, C.-H., Shih, C.-W., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H., and Chou, P.-T., J. Org. Chem., 2011, vol. 76, p. 8189. https://doi.org/10.1021/jo2008934

    Article  CAS  PubMed  Google Scholar 

  8. Chen, K.-Y., Cheng, Y.-M., Lai, C.-H., Hsu, C.-C., Ho, M.-L., Lee, G.-H., and Chou, P.T., J. Am. Chem. Soc., 2007, vol. 129, p. 4534. https://doi.org/10.1021/ja070880i

    Article  CAS  PubMed  Google Scholar 

  9. Baldridge, A., Kowalik, J., and Tolbert, L.M., Synthesis, 2010, vol. 14, p. 2424. https://doi.org/10.1055/S-0029-1218796

    Article  Google Scholar 

  10. Topuzyan, V.O., Arutyunyan, L.G., and Oganesyan, A.A., Russ. J. Org. Chem., 2007, vol. 43, p. 868. https://doi.org/10.1134/S1070428007060127

    Article  CAS  Google Scholar 

  11. Zhu, Q.Y., Hackman, R.M., and Ensunsa, J.L., J. Agric. Food Chem., 2002, vol. 50, p. 6929. https://doi.org/10.1021/jf0206163

    Article  CAS  PubMed  Google Scholar 

  12. Daina, A., Michielin, O., and Zoete, V., Sci. Rep., 2017, vol. 7, p. 42717. https://doi.org/10.1038/srep42717

    Article  PubMed  PubMed Central  Google Scholar 

  13. Cheng, F., Liu, C., Jiang, J., Lu, W., Li, W., Liu, G., Zhou, W., Huang, J., and Tang, Y., Plos Comput. Biol., 2012. https://doi.org/10.1371/journal.pcbi.1002503

  14. Egan, W.J., Merz, K.M. Jr., and Baldwin, J.J., J. Med. Chem., 2000, vol. 43, p. 3867. https://doi.org/10.1021/jm000292e

    Article  CAS  PubMed  Google Scholar 

  15. Lipinski, C., Drug Discov. Today: Technol., 2004, vol. 1, p. 337. https://doi.org/10.1016/j.ddtec.2004.11.007

    Article  CAS  Google Scholar 

  16. Martin, Y.C., J. Med. Chem., 2005, vol. 48, p. 3164. https://doi.org/10.1021/jm0492002

    Article  CAS  PubMed  Google Scholar 

  17. Steiner, T. and Koellner, G., J. Mol. Biol., 2001, vol. 305, p. 535. https://doi.org/10.1006/jmbi.2000.4301

    Article  CAS  PubMed  Google Scholar 

  18. Kumpf, R. and Dougherty, D., Science, 1993, vol. 261, p. 1708. https://doi.org/10.1126/science.8378771

    Article  CAS  PubMed  Google Scholar 

  19. Dighe, S.N., Deora, G.S., De la Mora, E., Nachon, F., Chan, S., Parat, M.O., and Ross, B.P., J. Med. Chem., 2016, vol. 59, p. 7683. https://doi.org/10.1021/acs.jmedchem.6b00356

    Article  CAS  PubMed  Google Scholar 

  20. Nachon, F., Ehret-Sabatier, L., Loew, D., Colas, C., van Dorsselaer, A., and Goeldner, M., Biochemistry, 1998, vol. 37, p. 10507. https://doi.org/10.1021/bi980536l

    Article  CAS  PubMed  Google Scholar 

  21. Masson, P., Carletti, E., and Nachon, F., Protein Pept. Lett., 2009, vol. 16, p. 1215. https://doi.org/10.2174/092986609789071207

    Article  CAS  PubMed  Google Scholar 

  22. Abdel-Galil, E., Moawad, E.B., El-Mekabaty, A., and Said, G.E., J. Heterocycl. Chem., 2018, vol. 55, p. 1092. https://doi.org/10.1002/jhet.3139

    Article  CAS  Google Scholar 

  23. Ellman, G., Courtney, K., Andres, V. Jr., and Feather-Stone, R., Biochem. Pharm., 1961, vol. 7, p. 88. https://doi.org/10.1016/0006-2952(61)90145-9

    Article  CAS  PubMed  Google Scholar 

  24. Narayanaswamy, V.K., Rissdörfer, M., and Odhav, B., Int. J. Theor. Appl. Sci., 2013, vol. 5, p. 43.

    CAS  Google Scholar 

  25. Evans, M.J. and Moore, J.S., J. Chem. Educ., 2011, vol. 88, p. 764. https://doi.org/10.1021/ed100517g

    Article  CAS  Google Scholar 

  26. https://www.rcsb.org/

  27. Trott, O. and Olson, A.J., J. Comput. Chem., 2010, vol. 31, p. 455. https://doi.org/10.1002/jcc.21334

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. BIOVIA, D.S. BIOVIA, Discovery, Studio, 2017, R2: A Comprehensive Predictive Science Application for the Life Sciences. San, Diego. https://discover.3ds.com/discovery-studio-visualizer-download

  29. http://www.swissadme.ch/

  30. https://www.cdc.gov/niosh/rtecs/default.html

  31. Bajda, M., Więckowska, A., Hebda, M., Guzior, N., Sotriffer, C.A., and Malawska, B., Int. J. Mol. Sci., 2013, vol. 14, p. 5608. https://doi.org/10.3390/ijms14035608

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, Armenia

    V. O. Topuzyan, A. A. Hovhannisyan & A. T. Makichyan

  2. Russian–Armenian University, 0051, Yerevan, Armenia

    A. T. Makichyan & L. S. Hunanyan

  3. Yerevan State University, 0025, Yerevan, Armenia

    L. Kh. Galstyan

Authors
  1. V. O. Topuzyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Hovhannisyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. T. Makichyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. S. Hunanyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. Kh. Galstyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. T. Makichyan.

Ethics declarations

The authors declare no conflict of interest.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Topuzyan, V.O., Hovhannisyan, A.A., Makichyan, A.T. et al. Application of the Benzoyl O-Protecting Group in the Synthesis of α,β-Dehydrotyrosine-containing Amides and Imidazolones. Russ J Org Chem 58, 236–243 (2022). https://doi.org/10.1134/S1070428022020117

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022020117

Keywords:

Search

Navigation