Comparative theoretical and experimental study on novel tri-quinoline system and its anticancer studies

Kasirajan Gayathri, Ramachandran Radhika, Ramasamy Shankar, Mahalingam Malathi, Krishnaswamy Savithiri, Hazel A. Sparkes, Judith A.K. Howard, Palathurai Subramaniam Mohan

Research output: Contribution to journalArticle (Academic Journal)peer-review

8 Citations (Scopus)
282 Downloads (Pure)

Abstract

A novel compound 2-chloro-3,6-bis-(quinolin-8-yloxymethyl)-quinoline 3 bearing a tri-quinoline moiety has been synthesized from 2-chloro-3,6-dimethyl quinoline 1 and 8-hydroxy quinoline 2 using dry acetone and K2CO3 as a base. 3 has been characterized by using FT-IR, FT-Raman, UV–Vis, 1H NMR, 13C NMR spectra and single crystal X-ray diffraction methods. We have also made a combined experimental and theoretical study on the molecular structure, vibrational spectra, NMR, FT-IR, FT-Raman and UV–Vis spectra of 2-chloro-3,6-bis-(quinolin-8-yloxymethyl)-quinoline. The theoretical studies of the title compound have been evaluated by using density functional theory calculations using B3LYP/6-31 + G(d,p) and M06-2X/6-31 + G(d,p) level of theories. The calculated theoretical values were found to be in good agreement with the experimental findings. The single crystal structure 3 crystallized in the orthorhombic space group Pna21. The compound 3 exhibits higher cytotoxicity in human cervical cancer cell lines (HeLa) than human breast cancer cell lines (MCF7).
Original languageEnglish
Pages (from-to)770-780
Number of pages11
JournalJournal of Molecular Structure
Volume1134
Early online date10 Jan 2017
DOIs
Publication statusPublished - 15 Apr 2017

Keywords

  • 2-Chloro-3,6-bis-(quinolin-8-yloxymethyl)-quinoline
  • Spectroscopic studies
  • Single crystal XRD
  • MEP
  • HOMO-LUMO
  • Cytotoxicity

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