Ultrasound-assisted synthesis of benzothiazepines and assessment of theirin vitroacetylcholinesterase inhibition activity

Abstract

A series of steroidal 1,5-benzothiazepine and its derivatives have been synthesized by the reaction of α,β-unsaturated ketones with 2-aminothiophenol using small amount of dimethylformamide (DMF) as a solvent and catalytic amount of acetic acid at 45-50°C under ultrasonic irradiation. This method provides several advantages such as the shortest reaction time, high yields, simple work-up procedure, and purification of products by nonchromatographic methods. All the synthesized compounds were screened for their acetylcholinesterase (AChE) inhibition activity. These compounds exhibited moderate AChE inhibition activity as compared to the standard drug, tacrine. Compound 5 showed the highest inhibition among all benzothiazepines. The AChE inhibition activity of the compound 5 was further investigated with the help of in silico docking study to predict the active sites.