Yb/chitosan catalyzed synthesis of highly substituted piperidine derivatives for potential nuclease activity and DNA binding study

Abstract

Background: Herein, a new chitosan supported ytterbium nano-catalyst has been prepared and used for mild, efficient, and expeditious method for the synthesis of substituted piperidine derivatives via three component condensation of substituted anilines, formaldehyde and different cyclic/acyclic active methylene compounds at room temperature. Methods: The catalyst was characterized by FTIR, XRD, SEM, EDX, TEM, ICP-AES and the stability of catalyst was evaluated by TG analysis. The synthesized compound 3,3,11,11-Tetramethyl-15-(phenyl)-15- azadispiro[5.1.5.3]hexadecane-1,5,9,13-tetrone (3a) was explored for pBR322 DNA cleavage activity and genotoxicity for the first time. Further, the interaction study of 3a with CT-DNA was investigated through UV-vis, Fluorescence and Viscosity method. Results: The successful preparation of Yb/chitosan nano-catalyst was proved using various techniques and the catalyst was found effective towards substituted piperidine formations with the catalyst reusability. Further, compound 3a was successfully tested for DNA cleavage activity. In addition, Fluorescence results revealed that compound 3a interacts with DNA having a binding affinity of 4.84 x 104 M-1 . Conclusion: Hence, it could be suggested that compounds bearing spiro-piperidine scaffold synthesized using reusable nano-catalyst would be an effective biological agent.