Synthesis, computational study, and antibacterial activity of rhodanine and thiazolidine-2,4-dione scaffolds
DOI:
https://doi.org/10.21271/ZJPAS.32.3.15Keywords:
Synthesis, computational study, 2-thioxothiazolidin-4-one, antibacterial activity, and thiazolidine-2,4-dione.Abstract
In this research, different thiazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives (1-13) have been synthesized by Knoevenagel Condensation (1-13). Thiazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives have an important role in medicinal chemistry and drug design. All synthesized compounds (1-13) have been confirmed by IR, ¹H and ¹³C-NMR spectral data. A computational study was used to determine values of the lowest unoccupied molecular orbital and highest occupied molecular orbital energy gap to show the chemical stability, and reactivity of compounds (1-13). Small values of energy between a lowest unoccupied molecular orbital and a highest occupied molecular orbital energy gap indicate chemical stability and reactivity of synthesized compounds. ELUMO-HOMO ranged between 0.004-0.306 eV indicated high reactivity of the prepared molecule. Thermodynamic energies have been calculated for synthesized compounds including Enthalpy, Entropy, and Gibbs free energy, negative values have been detected for all synthesized compounds (1-13).
Antibacterial activity has done for all synthesized compounds (1-13) against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli by the method of disc diffusion show that all synthesized compounds except 7, 8, 11 and 13 have antibacterial effect for both or one type of bacteria. Antibacterial activity is observed as a clear circular zone of inhibition for selected synthesized compounds by disc Inhibition zones of Staphylococcus aureus, and Escherichia coli bacteria. The range for Staphylococcus aureus were between (6-24 )mm and for Escherichia coli were between (6-18)mm, the measuring of the zones were with the discs.
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ABDULLAH, B. J., OMAR, M. S. & JIANG, Q. J. 2016. Grüneisen Parameter and Its Related Thermodynamic Parameters Dependence on Size of Si Nanoparticles. ZANCO Journal of Pure and Applied Sciences, 28, 126-132.
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AHN, J. H., KIM, S. J., PARK, W. S., CHO, S. Y., DU HA, J., KIM, S. S., KANG, S. K., JEONG, D. G., JUNG, S.-K. & LEE, S.-H. 2006. Synthesis and biological evaluation of rhodanine derivatives as PRL-3 inhibitors. Bioorganic & medicinal chemistry letters, 16, 2996-2999.
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CHONG, D. P., GRITSENKO, O. V. & BAERENDS, E. J. 2002. Interpretation of the Kohn–Sham orbital energies as approximate vertical ionization potentials. The Journal of Chemical Physics, 116, 1760-1772.
FAGHIHI, K. & HAGIBEYGI, M. 2003. New polyamides containing azobenzene unites and hydantoin derivatives in main chain: synthesis and characterization. European polymer journal, 39, 2307-2314.
GALVÁN, J. E., GIL, D. M., LANÚS, H. E. & ALTABEF, A. B. 2015. Theoretical study on the molecular structure and vibrational properties, NBO and HOMO–LUMO analysis of the POX3 (X= F, Cl, Br, I) series of molecules. Journal of Molecular Structure, 1081, 536-542.
JALBOUT, A. & FERNANDEZ, S. 2002. Part II. Gaussian, complete basis set and density functional theory stability evaluation of the singlet states of Cn (n= 1–6): energy differences, HOMO–LUMO band gaps, and aromaticity. Journal of Molecular Structure: THEOCHEM, 584, 169-182.
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JOHANSSON, P., NILSSON, H., JACOBSSON, P. & ARMAND, M. 2004. Novel Hückel stabilised azole ring-based lithium salts studied by ab initio Gaussian-3 theory. Physical Chemistry Chemical Physics, 6, 895-899.
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MURUGAN, R., ANBAZHAGAN, S. & NARAYANAN, S. S. 2009. Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3+ 2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives. European journal of medicinal chemistry, 44, 3272-3279.
PEARSON, R. G. & PEARSON, R. G. 2005. Chemical hardness and density functional theory. Journal of Chemical Sciences, 117.
RAJAMANIKANDAN, S., JEYAKANTHAN, J. & SRINIVASAN, P. 2017. Binding mode exploration of LuxR-thiazolidinedione analogues, e-pharmacophore-based virtual screening in the designing of LuxR inhibitors and its biological evaluation. Journal of Biomolecular Structure and Dynamics, 35, 897-916.
ROCHA, M., DI SANTO, A., ARIAS, J. M., GIL, D. M. & ALTABEF, A. B. 2015. Ab-initio and DFT calculations on molecular structure, NBO, HOMO–LUMO study and a new vibrational analysis of 4-(dimethylamino) benzaldehyde. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 136, 635-643.
ROMERO-GONZALEZ, J., PERALTA-VIDEA, J., RODRıGUEZ, E., RAMIREZ, S. & GARDEA-TORRESDEY, J. 2005. Determination of thermodynamic parameters of Cr (VI) adsorption from aqueous solution onto Agave lechuguilla biomass. The Journal of chemical thermodynamics, 37, 343-347.
SANDHU, J. S. 2013. Ultrasound-assisted synthesis of 2, 4-thiazolidinedione and rhodanine derivatives catalyzed by task-specific ionic liquid:[TMG][Lac]. Organic and medicinal chemistry letters, 3, 2.
SHANKAR, R., SENTHILKUMAR, K. & KOLANDAIVEL, P. 2009. Calculation of ionization potential and chemical hardness: a comparative study of different methods. International Journal of Quantum Chemistry, 109, 764-771.
SUN, G., XU, X., BICKETT, J. R. & WILLIAMS, J. F. 2001. Durable and regenerable antibacterial finishing of fabrics with a new hydantoin derivative. Industrial & engineering chemistry research, 40, 1016-1021.
SYLDATK, C., LÄUFER, A., MÜLLER, R. & HÖKE, H. 1990. Production of optically pure d-and l-α-amino acids by bioconversion of d, l-5-monosubstituted hydantoin derivatives. Microbial Bioproducts. Springer.
VEISI, H., NAEIMI, A., MALEKI, B., ASHRAFI, S. S. & SEDRPOUSHAN, A. 2015. Synthesis of 5-Alkylidene-2, 4-thiazolidinediones and Rhodanines Promoted by Propylamino-functionalized Nano-structured SBA-15. Organic Preparations and Procedures International, 47, 309-315.
VIKNESHVARAN, S. & VELMATHI, S. 2017. Interfacial properties of electron-donating and electron-withdrawing group-substituted chiral Schiff bases on mild steel corrosion in 1 M hydrochloric acid solution. Journal of Bio-and Tribo-Corrosion, 3, 19.
WANG, W., ZHOU, Y., PENG, H., HE, H.-W. & LU, X.-T. 2017. Synthesis and herbicidal activity of α-[(substituted phenoxybutyryloxy or valeryoxy)] alkylphosphonates and 2-(substituted phenoxybutyryloxy) alkyl-5, 5-dimethyl-1, 3, 2-dioxaphosphinan-2-one containing fluorine. Journal of Fluorine Chemistry, 193, 8-16.
YADAV, M., BEHERA, D., KUMAR, S. & YADAV, P. 2015. Experimental and quantum chemical studies on corrosion inhibition performance of thiazolidinedione derivatives for mild steel in hydrochloric acid solution. Chemical Engineering Communications, 202, 303-315.
YU, F.-L., SCHWALBE, C. H. & WATKIN, D. J. 2004. Hydantoin and hydrogen-bonding patterns in hydantoin derivatives. Acta Crystallographica Section C: Crystal Structure Communications, 60, o714-o717.
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