Skip to main content
SpringerLink
Log in

Four Three-winged Nitrogenous Heterocyclic Derivatives of Citric Acid Scaffold: The First Synthesis and Characterization of These Newly Discovered Fan-like Compounds

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

Abstract

Citric acid is a very important scaffold and intermediate in organic/medicinal chemistry and biochemistry, as it is the most famous natural tricarboxylic acid whose unique fan-like backbone with three reactive carboxy groups (three wings) and one hydroxy group (one stand or stick) represent a very rich reactive environment for several organic reactions. Derivatives of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles, and 1,2,4-triazoles exhibit diverse high pharmacological activity. According to the combination principles, if three substituted aromatic heterocyclic rings of the three previously-mentioned types are directly linked with a citric acid scaffold at the positions of the carboxy groups, the resulting derivatives are expected to be pharmaco­logically very active. This paper reports for the first time successful design, synthesis, and characterization of four three-winged nitrogenous heterocyclic derivatives of citric acid scaffold, which represent a new fan-shaped heteroaromatic pharmacophore.

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

Fig. 1.
Scheme

Similar content being viewed by others

REFERENCES

  1. Citric Acid (PubChem CID: 311). https://pubchem.ncbi.nlm.nih.gov/compound/Citric-acid

  2. Apelblat, A., Citric Acid, Cham: Springer, 2014. https://doi.org/10.1007/978-3-319-11233-6

  3. Verhoff, F.H. and Bauweleers, H., Ullmann’s Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2014. https://doi.org/10.1002/14356007.a07_103.pub3

  4. Lei, L., Ding, T, Shi, R., Liu, Q., Zhang, L., Chen, D., and Tian, W., Polym. Degrad. Stab., 2007, vol. 92, p. 389. https://doi.org/10.1016/j.polymdegradstab.2006.12.004

    Article  CAS  Google Scholar 

  5. Yang, J., Webb, A.R., Pickerill, S.J., Hageman, G., and Ameer, G.A., Biomaterials, 2006, vol. 27, p. 1889. https://doi.org/10.1016/j.biomaterials.2005.05.106

    Article  CAS  PubMed  Google Scholar 

  6. Tran, R.T., Wang, L., Zhang, C., Huang, M., Tang, W., Zhang, C., Zhang, Z., Jin, D., Banik, B., Brown, J.L., Xie, Z., Bai, X., and Yang, J., J. Biomed. Mater. Res., Part A, 2014, vol. 102, p. 2521. https://doi.org/10.1002/jbm.a.34928

    Article  CAS  Google Scholar 

  7. Shao, J., Chen, S., and Du, C., J. Mater. Chem. B, 2015, vol. 3, p. 5291. https://doi.org/10.1039/C5TB00535C

    Article  CAS  PubMed  Google Scholar 

  8. Stops, F., Fell, J.T., Collett, J.H., Martini, L.G., Sharma, H.L., and Smith, A.-M., Int. J. Pharm., 2006, vol. 308, p. 14. https://doi.org/10.1016/j.ijpharm.2005.09.039

    Article  CAS  PubMed  Google Scholar 

  9. Soccol, C.R., Vandenberghe, L.P.S., Rodrigues, C., and Pandey, A., Food Technol. Biotechnol., 2006, vol. 44, p. 141.

    CAS  Google Scholar 

  10. Rabie, A.M., MethodsX, 2020, vol. 7, article ID 100737. https://doi.org/10.1016/j.mex.2019.11.010

Download references

ACKNOWLEDGMENTS

I gratefully thank and deeply acknowledge the staff members and researchers of the Departments of Pharma­ceutical Organic Chemistry and Medicinal Chemistry (Faculty of Pharmacy, Mansoura University, Mansoura, Egypt) for their sincere support and interest to make this new discovery and work coming out to light.

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, 35516, Mansoura, Egypt

    A. M. Rabie

  2. Dr. Amgad Rabieʼs Research Lab. for Drug Discovery (DARLD), 35744, Mansoura, Egypt

    A. M. Rabie

Authors
  1. A. M. Rabie
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. M. Rabie.

Ethics declarations

The author declares no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rabie, A.M. Four Three-winged Nitrogenous Heterocyclic Derivatives of Citric Acid Scaffold: The First Synthesis and Characterization of These Newly Discovered Fan-like Compounds. Russ J Org Chem 57, 417–421 (2021). https://doi.org/10.1134/S1070428021030131

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021030131

Keywords:

Search

Navigation