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

Abstract

A novel compound 2-chloro-3,6-bis-(quinolin-8-yloxymethyl)-quinoline 3 bearing a triquinoline moiety has been synthesized from 2-chloro-3,6-dimethyl quinoline 1 and 8-hydroxy quinoline using dry acetone and K2CO3 as a base. 3 has been characterized by using FT-IR, FT-Raman, UV-Vis, 1 H NMR, 13 C 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). Highlights • A novel tri-quinoline was synthesized and optimized by density functional theories. • Single crystal XRD, FT-IR, Raman, 1 H, 13 C NMR and UV-Vis spectra were studied. • All the experimental data were compared with theoretical values. • Cytotoxicity was determined by MTT assay and by theoretical calculations.

Recent Advances in the Synthesis and Biological Activity of 8-Hydroxyquinolines

“…The target product was fully characterized by using various spectroscopic techniques and single-crystal X-ray diffraction method. This compound was screened against MCF-7 and Hela cancer cell lines using MMT assay, giving IC 50 values of 21.02 and 27.73 mM, respectively [ 35 ].…”

The solvatochromism and electronic structure of(E)-2-(2-hydroxystyryl)quinolin-8-ol

“…Quinoline derivatives have been used in many different applications such as optoelectronic materials and optical switches in nonlinear optics due to their unique electronic structure [1,2]. In addition, these compounds have some biological activities such as anticancer potential [1,3] and are used in the treatment of malaria, topical pathogenic parasitic Leishmania infection, antihepatitis B, etc. They have usage in textiles as well [4][5][6].…”