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Synthesis and Characterization of Benzothiophene-3-carbonitrile Derivative and Its Interactions with Human Serum Albumin (HSA)
Authors: Parveen, Mehtab; Aslam, Afroz; Alam, Mahboob; Siddiqui, Mohd Faizan; Bano, Bilqees; Azaz, Shaista; Silva, Manuela Ramos; Pereira Silva, P. S.
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 P2(1)/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 x 10(-4) mol(-1) and Gibbs free energy change (Delta G) of-6.8 kcal mol(-1). Molecular docking has been used to calculate the probable mode of interaction of compound 3 a with HSA.
