Soma Acharjee1, Asish Bhaumik*2, V. Shwetha3, Sk. Nagulmeera2, N. Santhosh Kumar2, M. Swapna2
1Department of Pharmaceutical Chemistry, Regional Institute of Pharmaceutical Science and Technology, Agartala, Tripura, India-799005.
2Department of Pharmaceutical Chemistry, Teja College of Pharmacy, Kodad, Nalgonda-508206, Telangana, India.
3Department of Pharmaceutical Analysis, Pratishta Institute of Pharmaceutical Sciences, Durajpally, Chivemla, Nalgonda-508214, Telangana State, India.
A B S T R A C T
The objective of the present work was the synthesis of N-[2-(4-substituted phenyl)-4-oxo-1,3-thiazolidine-3-yl]-2-(naphthalene-2-yloxy)acetamide and evaluation of in-vitro anticonvulsant activity by Molecular Docking against Voltage Sensitive Sodium Channel (VSSC) and the best dock pose was selected based on the interaction study analysis. Based on this a new series of compound had been planned to synthesize by reacting β-naphthol, ethyl chloroacetate, hydrazine monohydrate, ethyl alcohol and various aromatic aldehydes in presence of anhydrous potassium carbonate. The synthesized compounds were characterized by IR, NMR, and Mass spectroscopy. In silico.molecular docking studies displayed the following binding energies of the synthesized compounds (A1-A10): -5.32, -5.67, -5.20, -4.44, -4.54, -5.07, -4.77, -5.92, -6.23, -5.21 and -6.03 k.cal/mol of standard drug phenytoin, which indicated that the compounds had high binding affinity towards the VSSC protein and inhibit the sodium channel when compared with standard drug phenytoin. In vitro molecular docking also displayed the estimated inhibition constant of the synthesized compounds as: 125.26, 69.70, 155.24, 557.10, 466.77, 192.21, 318.48, 45.77, 27.29, and 150.74 uM (A1-A10) and 37.83 uM (Phenytoin).
Keywords: Thiazolidinone, Anticonvulsant activity, IR, NMR, Molecular docking, Binding energy