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, α-Glucosidase, Type-2 diabetes