SpringerLink
Log in

One-Pot Approach to N-Benzenesulfonyl Amino Acid Esters That Enhance Proline Content in Response to Excess Cadmium

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

Abstract

N-Benzenesulfonyl amino acid esters have drawn much attention due to their pharmacological and biological activity. Herein, a facile and effective one-pot approach to N-benzenesulfonyl amino acid esters has been developed, and 16 compounds have been obtained in excellent yields (90–95%) in a short time (9–14 min) using 4-bromobenzenethiol and amino acid esters as starting materials. Significantly, methyl 2-(4-bromoben­zene­sulfon­amido)acetate (3a) could enhance the proline content of soybean in response to excess cadmium in a way similar to the plant hormone abscisic acid.

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

Access this article

Log in via an institution

Price includes VAT (Germany)

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme

REFERENCES

  1. Sari, O., Boucle, S., Cox, B.D., Ozturk, T., Russell, O.I., Bassit, L., Amblard, F., and Schinazi, R.F., Eur. J. Med. Chem., 2017, vol. 138, p. 407. https://doi.org/10.1016/j.ejmech.2017.06.062

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Vatsal, M., Sharma, A., and Awasthi, P., Indian J. Chem., 2022, vol. 61, p. 442. https://doi.org/10.56042/ijc.v61i4.62579

    Article  CAS  Google Scholar 

  3. Gloulou, M., Kraiem, J., Jennene, F., Ghedira, D., Amor, H.B., Lajili, S., Jalleli, E., Ferjani, M., Bouraoui, A., and Kallel, M., Med. Chem. Res., 2016, vol. 25, p. 1497. https://doi.org/10.1007/s00044-016-1590-2

    Article  CAS  Google Scholar 

  4. Choi, J.Y., Fuerst, R., Knapinska, A.M., Taylor, A.B., Smith, L., Cao, X.H., Hart, P.J., Fields, G.B., and Roush, W.R., J. Med. Chem., 2017, vol. 60, p. 5816. https://doi.org/10.1021/acs.jmedchem.7b00514

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Hagimori, M., Temma, T., Kudo, S., Sano, K., Kondo, N., and Mukai, T., Bioorg. Med. Chem. Lett., 2018, vol. 28, p. 193. https://doi.org/10.1016/j.bmcl.2017.11.027

    Article  CAS  PubMed  Google Scholar 

  6. Dogan, B., Celik, M., Unal, M., Sefali, A., Martin, E., and Kaya, A., Turk. J. Bot., 2016, vol. 40, p. 130. https://doi.org/10.3906/bot-1412-34

    Article  CAS  Google Scholar 

  7. Dwivedi, S.K.D., Samanta, K., Yadav, M., Jana, A.K., Singh, A.K., Chakravarti, B., Mondal, S., Konwar, R., Trivedi, A.K., Chattopadhyay, N., Sanyal, S., and Panda, G., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 6816. https://doi.org/10.1016/j.bmcl.2013.10.013

    Article  CAS  PubMed  Google Scholar 

  8. Shagufta, Ahmad, I., and Panda, G., Eur. J. Med. Chem., 2017, vol. 133, p. 139. https://doi.org/10.1016/j.ejmech.2017.03.054

    Article  CAS  PubMed  Google Scholar 

  9. Chatterjee, I., Ali, K., and Panda, G., ChemMedChem, 2023, vol. 18, no. 5. https://doi.org/10.1002/cmdc.202200617

  10. Park, S.Y., Fung, P., Nishimura, N., Jensen, D.R., Fujii, H., Zhao, Y., Lumba, S., Santiago, J., Rod­rigues, A., Chow, T.F.F., Alfred, S.E., Bonetta, D., Finkelstein, R., Provart, N.J., Desveaux, D., Rod­riguez, P.L., McCourt, P., Zhu, J.K., Schroeder, J.I., Volkman, B.F., and Cutler, S.R., Science, 2009, vol. 324, p. 1068. https://doi.org/10.1126/science.1173041

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Ma, Y., Szostkiewicz, I., Korte, A., Moes, D., Yang, Y., Christmann, A., and Grill, E., Science, 2009, vol. 324, p. 1064. https://doi.org/10.1126/science.1172408

    Article  CAS  PubMed  Google Scholar 

  12. Okamoto, M., Peterson, F.C., Defries, A., Park, S.Y., Endo, A., Nambara, E., Volkman, B.F., and Cutler, S.R., Proc. Natl. Acad. Sci. U. S. A., 2013, vol. 110, p. 12132. https://doi.org/10.1073/pnas.1305919110

    Article  PubMed  PubMed Central  Google Scholar 

  13. Huang, Z.Y., Zhang, N., Zuo, H.W., Zeng, X.Q., and Liu, H., Chin. J. Org. Chem., 2022, vol. 42, p. 2947. https://doi.org/10.6023/cjoc202206040

    Article  CAS  Google Scholar 

  14. Nibbs, A.E., Montgomery, T.D., Zhu, Y., and Rawal, V.H., J. Org. Chem., 2015, vol. 80, p. 4928. https://doi.org/10.1021/acs.joc.5b00277

    Article  CAS  PubMed  Google Scholar 

  15. Xu, X.H., Zhen, J.S., Du, X., Yuan, H., Li, Y.H., Chu, M.H., and Luo, Y., Org. Lett., 2022, vol. 24, p. 853. https://doi.org/10.1021/acs.orglett.1c04144

    Article  CAS  PubMed  Google Scholar 

  16. Zhou, Y., Chen, H., Lei, P.P., Gui, C.M., Wang, H.F., Yan, Q.J., Wang, W., and Chen, F.E., Chin. Chem. Lett., 2022, vol. 33, p. 4850. https://doi.org/10.1016/j.cclet.2022.02.029

    Article  CAS  Google Scholar 

  17. Casaschi, A., Grigg, R., and Sansano, J.M., Tetrahedron, 2001, vol. 57, p. 607. https://doi.org/10.1016/S0040-4020(00)01030-9

    Article  CAS  Google Scholar 

  18. Yang, K., Ke, M.L., Lin, Y.G., and Song, Q.L., Green Chem., 2015, vol. 17, p. 1395. https://doi.org/10.1039/c4gc02236j

    Article  CAS  Google Scholar 

  19. Huang, Z.Y., Yang, J.F., Song, K., Chen, Q., Zhou, S.L., Hao, G.F., and Yang, G.F., J. Org. Chem., 2016, vol. 81, p. 9647. https://doi.org/10.1021/acs.joc.6b01725

    Article  CAS  PubMed  Google Scholar 

  20. Zhao, L., Yang, M.L., Chen, H.R., and Ding, M.W., Chin. J. Org. Chem., 2022, vol. 42, p. 3740. https://doi.org/10.6023/cjoc202204059

    Article  CAS  Google Scholar 

  21. Feng, Y.J., He, J., Wei, Y.T., Tang, T., Li, C.T., and Liu, P., Chin. J. Org. Chem., 2022, vol. 42, p. 226. https://doi.org/10.6023/cjoc202107045

    Article  CAS  Google Scholar 

  22. Tian, B.H., He, M.Z., Tang, S.X., Hewlett, I., Tan, Z.W., Li, J.B., **, Y.X., and Yang, M., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 2162. https://doi.org/10.1016/j.bmcl.2009.02.116

    Article  CAS  PubMed  Google Scholar 

  23. Leng, Y., Li, Y., Ma, Y.H., He, L.F., and Li, S.W., Environ. Sci. Pollut. Res., 2021, vol. 28, p. 6030. https://doi.org/10.1007/s11356-020-10843-8

    Article  CAS  Google Scholar 

  24. Liu, L., Li, S.X., Guo, J.H., Li, N., Jiang, M., and Li, X.N., J. Hazard. Mater., 2022, vol. 430. https://doi.org/10.1016/j.jhazmat.2022.128489

Download references

Funding

This work was supported by Natural Science Foundation of Hunan Province (youth project no. 2021JJ40515), Scientific Research Fund of Hunan Provincial Education Department (no. 21B0677), and Specialized Research Fund for High-Level Talented Person of Shaoyang University.

Author information

Authors and Affiliations

  1. College of Agriculture Forestry Ecology, Shaoyang University, 422000, Shaoyang, China

    Z. Y. Huang, X. H. Li, P. Yang, L. J. Chen & X. J. Yang

Authors
  1. Z. Y. Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. X. H. Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. J. Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. X. J. Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Z. Y. Huang.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Huang, Z.Y., Li, X.H., Yang, P. et al. One-Pot Approach to N-Benzenesulfonyl Amino Acid Esters That Enhance Proline Content in Response to Excess Cadmium. Russ J Org Chem 60, 728–733 (2024). https://doi.org/10.1134/S1070428024040237

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428024040237

Keywords:

Search

Navigation