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Synthesis and Characterization of Benzothiophene‐3‐carbonitrile Derivative and Its Interactions with Human Serum Albumin (HSA)
Authors: Mehtab Parveen; Afroz Aslam; Mahboob Alam; Mohd Faizan Siddiqui; Bilqees Bano; Shaista Azaz; Manuela Ramos Silva; P. S. Pereira da Silva
Ref.: ChemistrySelect 4, 11979-11986 (2019)
Abstract: A series of biologically active compounds, i. e., benzothiophene‐3‐carbonitrile derivatives, were synthesized from 1,3‐cyclohexanediones and malononitrile in the presence of base using the well‐known Gewald reaction. This recyclable approach resulted in significant improvement in overall yield (85‐90%), high purity and minimized production of chemical waste without using toxic reagents. The formation of compound, 2‐amino‐7‐oxo‐4,5,6,7‐tetrahydro‐1‐benzothiophene‐3‐carbonitrile (3 a) was additionally supported by X‐ray crystallography and was found to crystallize in P21/n space group. The mode of binding of 3 a with human serum albumin (HSA) was studied by FTIR, UV spectroscopy, fluorescence spectroscopy, circular dichroism (CD) and molecular docking studies. The fluorescence results establish that compound 3 a interacted with HSA via static quenching mechanism with a binding affinity of 11.49 × 10−4 mol−1 and Gibbs free energy change (ΔG) of−6.8 kcal mol−1. Molecular docking has been used to calculate the probable mode of interaction of compound 3 a with HSA.
