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Pak J Pharm Sci ; 33(2(Supplementary)): 847-854, 2020 Mar.
Article in English | MEDLINE | ID: mdl-32863261

ABSTRACT

Pyrazoline and benzimidazoles derivatives have been widely studied due to their potential applications in the medicinal field. In this research project, we have hybridized these two heterocyclic systems in the same molecule. A new series of compounds, 2-((3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)methyl)-1H-benzo[d]imidazole (5a-i) were synthesized through a multistep reaction. In the first step, chalcones 3a-i were prepared by coupling of various acetophenones and benzaldehydes under alkaline conditions. These chalcones were cyclized with hydrazine hydrate to form a series of pyrazolines which were finally coupled with 2-chloromethyl-1H-benzimidazole to get a new series of titled hybrid molecules. The structures of these compounds were elucidated by spectral (1H NMR and 13C NMR) analysis. The anti-diabetic potential of these compounds was studied by screening them for their α-glucosidase inhibition activity. The SAR was established through molecular docking analysis. Compound 5d appeared as effective inhibitor with IC50 = 50.06µM as compared to reference drug (acarbose) having IC50 = 58.8µM.


Subject(s)
Benzimidazoles/chemical synthesis , Benzimidazoles/pharmacology , Hypoglycemic Agents/chemistry , Hypoglycemic Agents/pharmacology , Pyrazoles/chemical synthesis , Pyrazoles/pharmacology , Benzaldehydes/chemical synthesis , Benzaldehydes/pharmacology , Chalcones/chemical synthesis , Chalcones/pharmacology , Hydrazines/chemical synthesis , Hydrazines/pharmacology , Molecular Docking Simulation/methods , Structure-Activity Relationship
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