Synthesis of 8-hydroxyquinolium chloroacetate and synthesis of complexes derived from 8-hydroxyquinoline, and characterization, density functional theory and biological studies

8‐Hydroxyquinolium chloroacetate (L1) was synthesized and characterized. The results suggest that L1 loses ethyl chloroacetate ion on coordination at low pH (2–5) and consequently it behaves as 8‐hydoxyquinoline (L2). Cu2+, Co2+, Pt4+, Pd2+, Au3+, Ag+ and Nd3+ complexes derived from L2 have been syn...

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Bibliographic Details
Published in:Applied organometallic chemistry 2015-04, Vol.29 (4), p.200-208
Main Authors: Mlahi, Mosaad R., Afsah, Elsayed M., Negm, Amr, Mostafa, Mohsen M.
Format: Article
Language:English
Subjects:
8-hydroxyquinolium chloroacetate
antioxidant activity
Biological
Chemical bonds
cytotoxic activity
Density functional theory
DFT calculations
Dipole moment
Ligands
Radicals
Spectra
spectral studies
Synthesis
Thermal measurements
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Summary:8‐Hydroxyquinolium chloroacetate (L1) was synthesized and characterized. The results suggest that L1 loses ethyl chloroacetate ion on coordination at low pH (2–5) and consequently it behaves as 8‐hydoxyquinoline (L2). Cu2+, Co2+, Pt4+, Pd2+, Au3+, Ag+ and Nd3+ complexes derived from L2 have been synthesized and characterized using spectral, magnetic and thermal measurements. L2 acts as a neutral bidentate ligand in the case of Cu2+, Co2+, Pt4+, Pd2+ and Nd3+ complexes and as a mononegative bidentate ligand in the case of Au3+ and Ag+ complexes. Octahedral geometry is proposed for Cu2+, Co2+ (grey) and Pt4+ complexes and square‐planar for Co2+ (green), Pd2+ and Au3+ complexes. The bond lengths, bond angles, chemical reactivities, binding energies and dipole moments for all compounds were evaluated using density functional theory and molecular electrostatic potential for L1. Superoxide dismutase radical scavenger‐like activity and cytotoxic activity of the complexes towards HepG2 liver cancer cells has been screened. Cytotoxicity measurements show that Ag+ and Pd2+ complexes have the highest cytotoxic activity while L1, Cu2+, Co2+ (grey), Co2+ (green), Pt4+ and Nd3+ complexes have no cytotoxic activity. Copyright © 2015 John Wiley & Sons, Ltd. Several complexes derived from 8‐hydroxyquinoline have been synthesized and characterized. Biological activity of the complexes have been screened.
ISSN:0268-2605
1099-0739
DOI:10.1002/aoc.3265