Synthesis, characterization and antibacterial activity of thiazolidine-4-one and imidazolidine-4-one derived from Mesalazine drug by microwave method

https://doi.org/10.53730/ijhs.v6nS1.8088

Authors

  • Abdullah Khalid Shehab Department of Chemistry, College of Education, University of Samarra, Samarra, Iraq
  • Malath Khalaf Rasheed Department of Chemistry, College of Education, University of Samarra, Samarra, Iraq

Keywords:

Mesalazine, thiazolidine-4-one, imidazolidine-4-one, antibacterial

Abstract

The Schiff bases (A1- A5) were produced from the reaction of the 5-aminosalicylic acid with a variety of aldehydes by microwave method. Schiff bases were reacted with thioglycolic acid to obtain thiazolidine-4-one compounds (A6 – A10). Imidazolidine-4-one compounds (A11 - A15) were prepared from the prepared Schiff bases with the amino acid (alanine). Spectroscopic methods were used to diagnose the produced compounds (IR, 1H-NMR). The biological activity against two types of bacteria Proteus mirabilis –GVe and Enterococcus faecalis +GVe have tested and compared with the Mesalazine drug. The results proved that some of the prepared compounds are effective against these bacteria at different concentrations of 5 mg/ml, 10 mg/ml, and 15 mg/ml.

Downloads

Download data is not yet available.

References

Joule JA, Mills K, Smith GF. Heterocyclic chemistry. CRC Press; 2020 Nov 25.

Sell CS. Chemistry and the Sense of Smell. John Wiley & Sons; 2014 Mar 26.

MOHAMMED AM, AL-SHEMARY RK. Metal complexes with heteroscorpionate ligand founded on the pyridinamine group: cyclin-dependent kinase 2 inhibitor antimicrobial, antioxidant, and in vitro cytotoxicity, notional studies. International Journal of Pharmaceutical Research. 2021 Jan;13(1).

Hanna. H, Juncheng .Z, Zude .O, Zhou.B, Meiying.L and Liu.Y, ",Journal of Natueal Science", Wuhan University, 1, 15, 7177, (2010).

Al-Khyaat AD. Preparation and identification of some new thiazolidine-4-one compounds from Schiff base derivatives. JOURNAL OF EDUCATION AND SCIENCE. 2020 Sep 1;29(3):142-56.

Wang SQ, Yan XW, Hu BL, Zhang XG. Transition-metal and base-free thioannulation of propynamides with sodium sulfide and dichloromethane for the selective synthesis of 1, 3-thiazin-4-ones and thiazolidine-4-ones. Tetrahedron. 2020 Mar 20;76(12):131021.

Gummidi L, Kerru N, Ebenezer O, Awolade P, Sanni O, Islam MS, Singh P. Multicomponent reaction for the synthesis of new 1, 3, 4-thiadiazole-thiazolidine-4-one molecular hybrids as promising antidiabetic agents through α-glucosidase and α-amylase inhibition. Bioorganic Chemistry. 2021 Oct 1;115:105210.

Pitta.I.R ; Mourao.R.H and Silva.T.G. Synthesis and Biological Activity of Novel Acridinylidene and Benzylidene thiazolidinediones. Eur. J. Med. Chem., 40, 1129- 1133, 2005.

Dr. Ning Xi , Dr. Longbin and Dr. Qi Huang, "Int. Comprehensive Heterocyclic Chemistry III :Volume 4, 2008, Pages 143-364.

HASSAN HA, ALHEETY KA, HASSAN DF. Synthesis and identification of novel 2 thioxo imidazolidin 4 one derivatives containing azo and ester groups. International Journal of Pharmaceutical Research. 2019 Jul;11(3).

Mahmood RM, Ghafil RA. Synthesis and Characterization some Imidazolidine Derivatives and Study the Biological Activity. Annals of the Romanian Society for Cell Biology. 2021 Mar 20:569-84.

Arif IA, Ahamed A, Kumar RS, Idhayadhulla A, Manilal A. Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives. Saudi journal of biological sciences. 2019 May 1;26(4):673-80.

Rodriguez F., Rozas I., Ortega J.E., Erdozain A.M., Meana J.J., Callado L.F.: J. Med. Chem. 52, 601 (2009).

Shaker RM, Abd El-Naby HA, Ahmed EK, Ibrahim MA, Gedamy SA. One-pot synthesis, theoretical study and antimicrobial activity of 5, 5′-(1, 4-phenylenebis-(methanylylidene)) Bis (3-Aryl (Alkyl)-2-thioxoimidazolidin-4-one) derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements. 2019 Feb 1;194(1-2):147-55.

Arif IA, Ahamed A, Kumar RS, Idhayadhulla A, Manilal A. Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives. Saudi Journal of Biological Sciences. 2019 May 1;26(4):673-80.

Elmi F, Movaghar AF, Elmi MM, Alinezhad H and Nikbakhsh N. Application of FT-IR spectroscopy on breast cancer serum analysis. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2017 Dec 5;187:87-91.

Ozaki Y, Huck C, Tsuchikawa S, Engelsen SB, editors. Near-Infrared Spectroscopy: Theory, Spectral Analysis, Instrumentation, and Applications. Berlin/Heidelberg, Germany: Springer; 2021.

Kanoun O. Impedance spectroscopy advances and future trends: A comprehensive review. Impedance Spectroscopy. 2018 Dec 17:1-22.

Markussen J, Schaumburg K. Reaction Mechanism in Trypsin Catalyzed Synthesis of Human Insulin Studied by 17O-NMR Spectroscopy. In17. Prague, Czechoslovakia, August 29–September 3, 1982 2019 May 20 (pp. 387-394).

Emsley JW, Lindon JC. NMR spectroscopy using liquid crystal solvents. Elsevier; 2018 Jan 10.

De Graaf RA. In vivo NMR spectroscopy: principles and techniques. John Wiley & Sons; 2019 Mar 11.

Raics M, Timári I, Szilágyi L, Gabius HJ, Kövér KE. Introducing 77 Se NMR Spectroscopy to Analyzing Galectin–Ligand Interaction. InGalectins 2022 (pp. 105-123).

World Health Organization. WHO Advisory Group on Integrated Surveillance of Antimicrobial Resistance (AGISAR): report of the 7th meeting, 17-20 October 2016, Raleigh, United States of America. World Health Organization; 2018.

Racovita S, Popa M, Atanase LI, Vasiliu S. Synthetic macromolecules with biological activity. Biological Macromolecules. 2022 Jan 1:305-35.

Published

29-05-2022

How to Cite

Shehab, A. K., & Rasheed, M. K. (2022). Synthesis, characterization and antibacterial activity of thiazolidine-4-one and imidazolidine-4-one derived from Mesalazine drug by microwave method. International Journal of Health Sciences, 6(S1), 12446–12456. https://doi.org/10.53730/ijhs.v6nS1.8088

Issue

Section

Peer Review Articles