Stereoselective synthesis and in-silico evaluation of C4-benzimidazolyloxyphenyl substituted trans-β-lactam derivatives as promising novel PPARγ activators. Issue 24 (17th December 2021)

• Record Type: Journal Article
• Authors: Bhalla, Jitender; Bari, Shamsher S.; Chaudhary, Ganga Ram; Kumar, Ashok; Rathee, Aditi; Sharma, Radhika; Bhalla, Aman
• Is Part Of: Synthetic communications. Volume 51:Issue 24(2021)
• Page Start: 3758
• Page End: 3767
• Publication Date: 2021-12-17
• Subjects: Antidiabetic -- benzimidazole -- β-lactam -- molecular docking -- PPAR -- stereoselective; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2021.1992441
• Languages: English
• ISSNs: 0039-7911

Abstract

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, –SC6 H5, –SeC6 H5, –OCH3, –C6 H4 .Cl( p ), –C6 H4 .OCH3 ( p ) and –CH2 C6 H5 . All compounds were characterized on the basis of various spectroscopic techniques (FT-IR, 1 H NMR, 13 C 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: UF0001