Benzodioxole grafted spirooxindole pyrrolidinyl derivatives: synthesis, characterization, molecular docking and anti-diabetic activity. Issue 37 (25th August 2022)

• Record Type: Journal Article
• Authors: Nivetha, Narayanasamy; Martiz, Reshma Mary; Patil, Shashank M.; Ramu, Ramith; Sreenivasa, Swamy; Velmathi, Sivan
• Is Part Of: RSC advances. Volume 12:Issue 37(2022)
• Page Start: 24192
• Page End: 24207
• Publication Date: 2022-08-25
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2ra04452h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A highly stereoselective, three-component method has been developed for the synthesis of pyrrolidine and pyrrolizidine containing spirooxindole derivatives that exhibits excellent anti-diabetic activity. Abstract : A highly stereoselective, three-component method has been developed to synthesize pyrrolidine and pyrrolizidine containing spirooxindole derivatives. The interaction between the dipolarophile α, β-unsaturated carbonyl compounds and the dipole azomethine ylide formed in situ by the reaction of 1, 2-dicarbonyl compounds and secondary amino acids is referred to as the 1, 3-dipolar cycloaddition reaction. The reaction conditions were optimized to achieve excellent stereo- and regioselectivity. Shorter reaction time, simple work-up and excellent yields are the salient features of the present approach. Various spectroscopic methods and single crystal X-ray diffraction examinations of one example of compound 6i validated the stereochemistry of the expected products. The anti-diabetic activity of the newly synthesized spirooxindole derivatives was tested against the α-glucosidase and α-amylase enzymes. Compound 6i was found to exhibit potent inhibition activity against α-glucosidase and α-amylase enzymes which is further evidenced by molecular docking studies.