Computational investigation of molecular structures, spectroscopic properties and antitumor-antibacterial activities of some Schiff bases
Citation
Kaya, S., Karakaş, D., Erkan, S., Sivas Cumhuriyet Üniversitesi, Fen Fakültesi, Kimya Bölümü, 58140 Sivas, TürkiyeAbstract
Molecular structures, spectroscopic properties (IR, 1
H NMR and 13C NMR, UV-VIS), molecular electrostatic poten tial maps and some molecular properties (ionization energy, electron affinity, energy gap, hardness, electroneg ativity, electrophilicity index, static dipole moment and average linear polarizability) of three Schiff bases which
are 2-((ethylamino)methyl)-6-methoxyphenol (HL1), 2-((ethylamino) methyl)-6-methylphenol (HL2) and
2-((ethylamino)methyl)-6-chlorophenol (HL3) were computed at B3LYP/6-31G(d) level in aqueous phase.
The effects of methoxy, methyl and chloro substituents on Schiff bases were examined and it was found that
the electron donating property of methyl and chlorine substituents was higher than the methoxy substituent.
In order to investigate the antitumor activities of Schiff bases were docked against the breast cancer (MCF7)
cell line. Molecular docking results were compared with antitumor standard 5-fluorouracil. Antitumor activity
of HL2 and HL3 molecule was found to be higher than HL1 against MCF-7 cell line. In addition, in order to predict
the antibacterial activities of Schiff bases were docked against the Mycobacterium tuberculosis (H37Rv) cell line.
Docking results were compared with the antibacterial reference N-(salicylidene)-2-hydroxyaniline. Antibacterial
activity of HL2 and HL3 molecules was found to be higher than HL1. It is estimated that the binding of the electron
donating group to the ortho position of the hydroxyl group in studied Schiff bases increases both antitumor and
antibacterial activity.