Tropical Journal of Pharmaceutical Research

Original Research Article | OPEN ACCESS

Synthesis of 2-[2,3-dihydro-1,4-benzodioxin-6-yl(phenylsulfonyl)amino]-N-(un/substituted-phenyl)acetamides as anti-diabetic agents

Muhammad Athar Abbasi¹ , Sobia Parveen¹, Aziz-ur-Rehman¹, Sabahat Zahra Siddiqui¹, Misbah Irshad², Syed Adnan Ali Shah³, Muhammad Ashraf⁴

¹Department of Chemistry, Government College University, Lahore-54000, Pakistan; ²Department of Chemistry, Division of Science and Technology, University of Education, Township Campus, Lahore-54770, Pakistan; ³Faculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia; ⁴Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan.

For correspondence:- Muhammad Abbasi Email: atrabbasi@yahoo.com

Accepted: 12 October 2022 Published: 30 November 2022

Citation: Abbasi MA, Parveen S, Aziz-ur-Rehman , Siddiqui SZ, Irshad M, Shah SA, et al. Synthesis of 2-[2,3-dihydro-1,4-benzodioxin-6-yl(phenylsulfonyl)amino]-N-(un/substituted-phenyl)acetamides as anti-diabetic agents. Trop J Pharm Res 2022; 21(11):2411-2418 doi: 10.4314/tjpr.v21i11.21

© 2022 The authors.
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Abstract

Purpose: To synthesize a series of new 2-[2,3-dihydro-1,4-benzodioxin-6-yl(phenylsulfonyl)amino]-N-(un/substituted-phenyl) acetamides, and evaluate their anti-diabetic potentials.

Methods: Synthesis of the parent compound N-(2,3-dihydro-1,4-benzodioxin-6-yl) benzenesulfonamide (3) was carried out by reacting 2,3-dihydro-1,4-benzodioxin-6-amine (1) with benzenesulfonylchloride (2) in aqueous basic medium under definite pH controls. After that 3 was further treated with various 2-bromo-N-(un/substituted-phenyl)acetamides (6a-l) to yield new compounds (7a-l) in polar aprotic solvent, DMF (dimethylformamide), using LiH as activator. The proposed structures of the synthesized compounds were confirmed using proton-nuclear magnetic resonance (¹H-NMR) and infra-red spectroscopy (IR), and CHN analysis. Their anti-diabetic potential was evaluated by α-glucosidase enzyme inhibitory studies.

Results: All the new compounds demonstrated weak (7a-h, 7j and 7l) to moderate (7i and 7k) inhibitory activities against α-glucosidase enzyme. IC₅₀ (50 % inhibition concentration) values for 7i and 7k were 86.31±0.11 μM and 81.12±0.13 μM, respectively relative to acarbose (reference standard) with IC₅₀ of 37.38±0.12 μM.

Conclusion: All the synthesized compounds have weak to moderate activity against α-glucosidase enzyme. These compounds can thus be considered as possible therapeutic entrants for type-2 diabetes.

Keywords: 2,3-Dihydro-1,4-benzodioxin-6-amine, Benzenesulfonyl chloride, Anti-diabetic, Î±-Glucosidase, Type-2 diabetes