Synthesis of some thiazolidine-4-one derivatives of Isoniazid by using the microwave method and evaluation of their antibacterial and antifungal activity
Abstract
In this research, several Schiff bases [A1-A5] were prepared by reacting isoniazid with some aldehydes such as (4-hydroxybenzaldehyde, 3-nitro-4-hydroxybenzaldehyde, 4,3-dichlorobenzaldehyde, 4-hydroxy-3,5-dimethoxybenzaldehyde, pyrrole -2-carbaldehyde) by microwave method. In the same way, some ketones such as (Isatin and 4-aminoacetophenone) were used with Isoniazid to prepare Schiff bases [A6, A7]. Derivatives of thiazolidine-4-one (A8-A14) were prepared through the reaction of Schiff bases [A1-A7] with thioglycolic acid using dry benzene as a solvent and the reaction was done by microwave device. The prepared compounds were identified by infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance spectrometry as well as the change in color and melting point. The results of the biological activity of the prepared compounds showed high inhibitory activity at concentrations of 5, 10, and 15 mg/ml against the fungus Aspergillus sp. and against two types of bacteria isolates, GVe+ Streptococcus pneumonia, and GVe- Pseudomonas aeruginous, and the results were compared with the standard antibiotics Nystatin, Isoniazid l and Sulfamethoxazole.
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References
Anderson, P. O. Hand Book of Clinical Drug Data. 10th Ed., Mc-Graw Hill Company, New York, 2002; p. 83.
British Pharmacopeia. 3rd Ed., system simulation Ltd., The Stationary Office, London. 2000.
Rang, H. P. and Dale, M. M. Pharmacology. Churchill Livingstone, Edinburgh 1987; p.643.
Volynets, G.P.; Tukalo, M.A.; Bdzhola, V.G.; Derkach, N.M.; Gumeniuk, M.I.; Tarnavskiy, S.S.; Yarmoluk, S.M. Novel isoniazid derivative as promising antituberculosis agent. Future Microbiol. 2020, 15, 869–879.
Rozycka, D.; Korycka-Machala, M.; Zaczek, A.; Dziadek, J.; Gurda, D.; Orlicka-Plocka, M.; Wyszko, E.; Biniek-Antosiak, K.; Rypniewski, W.; Olejniczak, A.B. Novel Isoniazid-Carborane Hybrids Active in Vitro Against Mycobacterium tuberculosis. Pharmaceuticals 2020, 13, 465.
Rani, A.; Johansen, M.D.; Roquet-Baneres, F.; Kremer, L.; Awolade, P.; Ebenezer, O.; Singh, P.; Sumanjit; Kumar, V. Design and synthesis of 4-Aminoquinoline-isoindoline-dione-isoniazid triads as potential anti-mycobacterials. Bioorg. Med. Chem. Lett. 2020, 30, 127576.
Jeyaraman, P.; Alagarraj, A.; Natarajan, R. In silico and in vitro studies of transition metal complexes derived from curcuminisoniazid Schiff base. J. Biomol. Struct. Dyn. 2020, 38, 488–499
Munson, J. W. and Connors, K. A. Spectrophotometric determination of acid hydrazidesvianickel (II)-catalyzed hydroxamic acid formation. Journal of Pharmaceutical Sciences 1972; 61(2): 211–213.
Uddin, N.; Rashid, F.; Ali, S.; Tirmizi, S.A.; Ahmad, I.; Zaib, S.; Zubair, M.; Diaconescu, P.L.; Tahir, M.N.; Iqbal, J.; et al. Synthesis, characterization, and anticancer activity of Schiff bases. J. Biomol. Struct. Dyn. 2020, 38, 3246–3259.
Hanna. H, Juncheng .Z, Zude .O, Zhou.B, Meiying.L and Liu.Y, ",Journal of Natueal Science", Wuhan University, 1, 15, 7177, (2010).
Toliwal.S. D, Jadav.K. and Pavagadhi.T, " Inhibition of corrosion of mild steel in 1 N HCl solutions by Schiff base derived from non-traditional oils " J. Sci. Ind. Res. 2010, 69: 43-47.
Alam.M. S, Choi.J. H and Lee.D. U. " Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2- phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity" Bioorg. Med. Chem. 2012,20 (13): 4103-4108.
Dhanaraj.C. J , Johnson.J, Joseph.J and Joseyphus.R. S, " Synthesis, crystal structure, fluorescence, electrochemical property, and SOD-like activity of an unexpected nickel(II) complex with a quinazoline-type ligand " J. Coord. Chem. 2013, 66 (8): 1416-1450.
Abhinit.M , Ghodke.M and Pratima.N. A. Exploring Potential of 4-thiazolidinone: A brief review, Int. J of Pharmacy Pharmaceutical Sci. 2009, 1 , 47-64.
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.
Cunico.W , Gomes.C. R and Vellasco. W. T,. Chemistry and Biological Activities of 1,3-Thiazolidin-4-ones. Mini-Reviews in Organic Chemistry, 2008, 5, 336-344.
Joule .J. A. and Mills .K " Fundamentals of heterocyclic chemistry ", 5th edu. (2010).
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.
Emily M., "Fourier Transform Infrared Spectroscopy (FTIR):Methods, Analysis and Research Insights Chemical engineering methods, and technology", (2016),55-57.
Kainosho M, Miyanoiri Y, Takeda M. Isotope-aided methods for biological NMR spectroscopy: past, present, and future. InExperimental Approaches of NMR Spectroscopy 2018 pp. 37-61. Springer, Singapore.
Alberto Tampieri , Márk Szabó, Francesc Medina and Henrik Gulyás. A brief introduction to the basics of NMR spectroscopy and selected examples of its applications to materials characterization. From the journal Physical Sciences Reviews. Published by De Gruyter June 3, 2020.
https://doi.org/10.1515/psr-2019-0086.
Malath Khalaf Rasheed and Diana AbdAlkreem.Al-Rifaie, Synthesis some of thiazolidinoneand tetrazole compounds derived from acriflavine and evaluation of their antimicrobial, antifungal and an
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