Design, Synthesis and Investigation of Mefenamic Acid Containing Thiazolidine-4-one

Rawha'a Khalid M; Ayad Suliman H; Fahdel Dawood Kh

doi:10.55544/jrasb.2.5.24

Authors

Rawha'a Khalid M Department of Chemistry, College of Sciences, University of Tikrit, Tikrit, IRAQ.
Ayad Suliman H Department of Chemistry, College of Pure Sciences, University of Tikrit, Tikrit, IRAQ.
Fahdel Dawood Kh Department of Chemistry, College of Sciences, University of Tikrit, Tikrit, IRAQ.

DOI:

https://doi.org/10.55544/jrasb.2.5.24

Keywords:

Thiazolidine-4-one, Mefenamic Acid

Abstract

Mefenamic acid and chloroacetyl chloride were mixed together to make 2-(2-chloro-N-(2,3-dimethylphenyl) acetamido) benzoic acid. The last compound prepared reacted with hydrazine hydrate to get 2-(N-(2,3-dimethylphenyl)-2-hydrazineylacetamido) benzoic acid, Condensed substituted benzaldehydes were utilized to make Schiff bases; Through cyclization reactions with thioglycolic acid, these compounds were transformed into 2,3-disubstituted thiazolidine-4-one; and finally, all structures were described using FT-IR, 1H-NMR, and mass spectrometry.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

References

D. Utami, I. Nugrahani, and S. Ibrahim, “Formation and characterization of mefenamic acid-nicotinamide cocrystal during comilling based on X-ray powder diffraction analysis,” J. Appl. Pharm.Sci., vol. 6, no. 10, pp. 075–081, 2016, doi: 10.7324/JAPS.2016.601010.

P. A. R., “Drug Development of Mefenamic Acid Derivatives as Analgesic by Molecular Approach,” Int. J. Pharm. Clin. Res., vol. 9, no. 2, pp. 123–130, 2017, doi: 10.25258/ijpcr.v9i2.8294.

M. N. Somchit, F. Sanat, G. E. Hui, S. I. Wahab, and Z. Ahmad, “Mefenamic acid induced nephrotoxicity: An Animal Model,” Adv. Pharm. Bull., vol. 4, no. 4, pp. 401–404, 2014, doi: 10.5681/apb.2014.059.

D. P. Kemisetti, S. Manda, J. Aukunuru, K. M. Chinnala, and N. K. Rapaka, “Synthesis of prodrugs of mefenamic acid and their in vivo evaluation,” Int. J. Pharm. Pharm. Sci., vol. 6, no. 7, pp. 437–442, 2014.

E. Dilek, S. Caglar, N. Dogancay, B. Caglar, O. Sahin, and A. Tabak, “Synthesis, crystal structure, spectroscopy, thermal properties and carbonic anhydrase activities of new metal(II) complexes with mefenamic acid and picoline derivatives,” J. Coord. Chem., vol. 70, no. 16, pp. 2833–2852, 2017, doi: 10.1080/00958972.2017.1366996.

L. Zapała, M. Kosińska, E. Woźnicka, Ł. Byczyński, and W. Zapała, “Synthesis, spectral and thermal study of La(III), Nd(III), Sm(III), Eu(III), Gd(III) and Tb(III) complexes with mefenamic acid,” J.Therm. Anal. Calorim., vol. 124, no. 1, pp. 363–374, 2016, doi: 10.1007/s10973-015-5120-0.

E. O. F. Spherical, A. Crystals, L. Fast, T. For, E. The, and M. Acid, “Design and Evaluation of Spherical Agglomerated Crystals Loaded Fast Disolving Tablets for Enhancing the Solubilityof,” vol. 4, no. 11, pp. 4610–4616, 2017.

E. Zaini, L. Fitriani, R. Y. Sari, H. Rosaini, A. Horikawa, and H. Uekusa, “Multicomponent Crystal of Mefenamic Acid and N-Methyl- D-Glucamine: Crystal Structures and Dissolution Study,” J. Pharm.Sci., vol. 108, no. 7, pp. 2341–2348, 2019, doi: 10.1016/j.xphs.2019.02.003.

N. Kumar, L. S. Chauhan, C. S. Sharma, N. Dashora, and R. Bera, “Synthesis, analgesic and anti-inflammatory activities of chalconylincorporated hydrazone derivatives of mefenamic acid,” Med. Chem. Res., vol. 24, no. 6, pp. 2580–2590, 2015, doi: 10.1007/s00044-015- 1318-8.

C. Konnerth, V. Braig, A. Ito, J. Schmidt, G. Lee, and W. Peukert, “Formation of Mefenamic Acid Nanocrystals with Improved Dissolution Characteristics,” Chemie-Ingenieur-Technik, vol. 89, no. 8, pp. 1060–1071, 2017, doi: 10.1002/cite.201600190.

P. Chatterjee, T. Dey, S. Pal, and A. K. Mukherjee, “Two mefenamic acid derivatives: Structural study using powder X-ray diffraction, Hirshfeld surface and molecular electrostatic potential calculations,” Zeitschrift fur Krist. - Cryst. Mater., vol. 232, no. 5, pp. 385–394, 2017, doi: 10.1515/zkri-2016-2009.

William H. Brown, Brent L. Iverson, Eric V. Anslyn, Christopher S. Foote, Organic Chemistry, 7Ed, Wadsworth Cengage Learning, (2014).

Jonathan Clayden, Nick Greeves, Stuart Warren,ORGANIC chemistry,2Ed,Oxford University Press Inc,2012.

Robert M. Silverstein, Francis X. Webster, David J. Kiemle, spectrometric Identification of Organic compounds, 7th Ed, John- Wiley & Sons, INC, (2005)