Synthesis and the biological activity of bis-mefenamidocalixarene

Authors

DOI:

https://doi.org/10.24959/175951

Keywords:

calixarenes, conjugates, diaminocalix[4]arene, bis-mefenamidocalixarene, mefenamic acid, non-steroidal anti-inflammatory drugs, anti-exudative activity

Abstract

Aim. To develop the method for the synthesis of the conjugate of diaminocalix[4]arene with 2-(2,3-dimethylphenyl)aminobenzoic acid (mefenamic acid) – bis-mefenamidocalixarene, determine its structure and physicochemical properties and assess its anti-exudative activity (AeA).
Results and discussion. The conjugate of diaminocalixarene with mefenamic acid – bis-mefenamidocalixarene was synthesized at one step by the reaction of reactants in equimolar amounts in the presence of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide. The structure of the compound obtained was determined by spectral methods. AeA of bis-mefenamidocalixarene was studied in rats using the model of formalin edema. The results of the experimental studies showed that bis-mefenamidocalixarene exhibited the anti-exudative activity, which was equal to the reference drug – sodium diclofenac.
Experimental part. The reaction of diaminocalixaren with 2- (2,3-dimethylphenyl)aminobenzoic acid (mefenamic acid) led to bis-mefenamidocalixarene with 40 % yield. The screening of AeA was carried out using modern digital plethysmometer (IITC Life Science (USA)).
Conclusions. The effective one-stage method for the synthesis of the conjugate of diaminocalix[4]arene with 2-(2,3-dimethylphenyl)aminobenzoic acid – bis-mefenamidocalixarene has been developed. Its structure has been proven, and AeA has been studied. AeA is equal to the reference drug. It has been found that bis-mefenamidokalixaren synthesized is a promising compound for further profound studies.

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References

  1. Viktorov, O. P., Dmitriieva, T. Yu., Bazyka, O. S., Dziak, S. I. (2005). Ukrainskyi revmatolohichnyi zhurnal, 2 (20), 3–7.
  2. Gladkih, F. V. (2017). Obzory po klinicheskoj farmakologii i lekarstvennoj terapii, 15(4), 14–23.
  3. Holovach, I. Yu. (2016). Ukrainskyi revmatolohichnyi zhurnal, 1 (63), 48–51.
  4. Golovach, I. (2017). Strategic decisions for safe and potential long-term therapy of osteoarthritis with NSAIDs. Trauma, 18 (4), 27–34. https://doi.org/10.22141/1608-1706.4.18.2017.109341
  5. Demeckaja, A. (2017). Farmacevt praktik, 2, 28–29.
  6. Dzjak, G. V., Viktorov, A. P., Grishina, E. I. (1999). Nesteroidnye protivovospalitel’nye preparaty. Kyiv : Morion, 112.
  7. Gutsche, C. D. (2008). Calixarenes : An Introduction. Royal Society of Chemistry Cambridge, 276.
  8. Rodik, R. V., Boyko, V. I., Kalchenko, V. I. (2016). Calixarenes in Biotechnology and Bio-Medical Research. Frontiers in Medicinal Chemistry, 8, 206–301. https://doi.org/10.2174/9781681081755116080008
  9. Nimse, S. B., Kim, T. (2013). Biological applications of functionalized calixarenes. Chem. Soc. Rev., 42 (1), 366–386. https://doi.org/10.1039/c2cs35233h
  10. Da Silva, E., Lazar, A. N., Coleman, A. W. (2004). Biopharmaceutical applications of calixarenes. Journal of Drug Delivery Science and Technology, 14 (1), 3–20. https://doi.org/10.1016/s1773-2247(04)50001-1
  11. Rodik, R., Boiko, V., Danylyuk, O., Suwinska, K., Tsymbal, I., Slinchenko, N., … Kalchenko, V. (2005). Calix[4]arenesulfonylamidines. Synthesis, structure and influence on Mg2+, ATP-dependent calcium pumps. Tetrahedron Letters, 46 (43), 7459–7462. https://doi.org/10.1016/j.tetlet.2005.07.069
  12. Rybolovlev, Ju. R., Rybolovlev, R. S. (1979). Doklady AN SSSR, 6, 1513–1516.
  13. Stefanov, O. V. (2001). Doklinichni doslidzhennia likarskykh zasobiv: metodychni rekomendatsii. Kyiv, 527.
  14. Mironova, A. N., Bunjatjan, N. D., Vasil’eva, A. N. (Eds.). (2012). Rukovodstvo po provedeniju doklinicheskih issledovanij lekarstvennyh sredstv. Chast’ pervaja. Moscow : Grif i K, 944.
  15. Habrieva, U. (Ed.). (2005). Rukovodstvo po jeksperimental’nomu (doklinicheskomu) izucheniju novyh farmakologicheskih veshhestv. Moscow : Medicina, 832.

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Published

2019-08-20

How to Cite

(1)
Chalenko, N. M.; Rodik, R. V.; Syrova, G. O. Synthesis and the Biological Activity of Bis-Mefenamidocalixarene. J. Org. Pharm. Chem. 2019, 17, 21-25.

Issue

Vol. 17 No. 3(67) (2019)

Section

Original Researches

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