Abstract
A convenient and stereoselective synthesis of a novel series of C4-benzimidazolyloxyphenyl substituted trans-β-lactam derivatives is described. The scope of the reaction was examined by varying different aromatic and aliphatic functionalities on ketene and imine viz. –Cl, –SC6H5, –SeC6H5, –OCH3, –C6H4.Cl(p), –C6H4.OCH3(p) and –CH2C6H5. All compounds were characterized on the basis of various spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, elemental and mass analysis). The trans- or cis-configuration of β-lactams (4, 5) was assigned with respect to the relative position of C3-H and C4-H. The molecular docking studies were performed between representative compounds and PPARγ receptors which revealed that functionality at N1 significantly affects the binding affinity of the compounds in comparison to functionality at C3 of β-lactam unit. The in-silico studies lead to the identification of β-lactam 4a as potential candidate for development of future antidiabetic agents.
Graphical Abstract
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Acknowledgments
We acknowledge the Sophisticated Analytical Instrumentation Facility (SAIF), Panjab University, Chandigarh, India.