Ultrasound assisted synthesis of 2, 4-substituted 1, 5- benzothiazepine derivatives

Mangesh Ghodke,Anna Pratima Nikalje,Suvarna Wagh,Julio Seijas Vázquez

doi:10.3390/ecsoc-23-06704

Mangesh Ghodke, Anna Pratima Nikalje + Show 2 more

Open Access

https://doi.org/10.3390/ecsoc-23-06704

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Abstract

A series of 15 novel derivatives of Synthesis of 2, 4-substituted 1, 5- benzothiazepine 5a–l were synthesized in good yield from the key compound 1, 3-substituted-prop-2-en-1-one (3a-l), called chalcone, with 2-aminothiophenol (0.01mol) and pinch of zirconium oxychloride and solvent dimethyl formamide (DMF), by using ultra-sonication as one of the green chemistry tools. All the synthesised compounds were evaluated for anticonvulsant activity. The synthesized derivatives were investigated for CNS depressant, maximal electroshock seizure (MES), subcutaneous pentylenetetrazole (sc-PTZ) induced seizure and neurotoxicity screening.

Highlights

Synthesis of nitrogen and sulphur containing heterocycles is of current interest because of their useful, broad spectrum biological activities
1,5-benzothiazepine derivatives are well known on account of their wide synthetic applications and biological/pharmaceutical values
The 1,5-benzothiazepine scaffold has been used as cardiovascular modulator[1] such as vasodilator[2,3] and antiarrythmic[4] antagonists of several G-protein coupled receptors such as cholecystokinin (CCK) receptor[5], antiulcer activity[6], spasmolytic activities[78], ACE inhibitors[9], the angiotensin II receptor (ACE) inhibitors[10]

Summary

Introduction

Synthesis of nitrogen and sulphur containing heterocycles is of current interest because of their useful, broad spectrum biological activities. The heterocycle such as 1,5-benzothiazepine have gained attention of medicinal chemists due to their use as drugs and medicaments in a large number of diseases. Ultrasound-promoted synthesis has various advantages over conventional synthesis techniques such as reactions were carried at room temperature and require much less time for completion saves time and electricity, highly accelerated reaction rate, requires use of very less amount of solvents, shortened work-up procedure. In this research work we are reporting the synthesis of 2, 4-substituted 1, 5- benzothiazepine 5(a-l) derivatives in excellent yield using eco- friendly, prompt and suitable ultrasound-assisted green chemistry protocol

Results and Discussion

Methods

Step II

Conclusions