Design, stereoselective synthesis, computational studies and cholinesterase inhibitory activity of novel spiropyrrolidinoquinoxaline tethered indole hybrid heterocycle

Arumugam N., Almansour A. I., Kumar R. S., Yeswanthkumar S., Padmanaban R., Arun Y., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1225, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1225
  • Publication Date: 2021
  • Doi Number: 10.1016/j.molstruc.2020.129165
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Spiropyrrolidines, Quioxalinone, 1,3-dipolar cycloaddition, dft-calculation, X-ray diffraction analysis, Molecular docking simulation, SPIROOXINDOLE NATURAL-PRODUCTS, IONIC LIQUID, PYRROLIDINE, DERIVATIVES, DOCKING, REGIO
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

A facile eco-friendly approach for the regioand stereoselective synthesis of structurally intriguing novel spiropyrrolidinoquinoxaline tethered indole hybrid heterocycle has been accomplished via a cascade reaction sequence involving 1,3-dipolar cycloaddition as the key step. Structural elucidation of the synthesized spiroheterocycle was performed by NMR spectroscopy, mass spectrometric analysis and the stereochemistry of asymmetric carbons have been confirmed by single crystal X-ray diffraction analysis. The mechanistic rationalization for the formation of spiroheterocyclic hybrid was investigated through density functional theory (DFT) calculations. In addition, the synthesized spiroheterocyclic hybrid was tested for its cholinesterase inhibitory activity against ChEs and displayed good activity when compared to the standard drug galantamine. (C) 2020 Elsevier B.V. All rights reserved.