TY - JOUR
T1 - Novel palladium(II) and platinum(II) complexes with 1H-benzimidazol-2- ylmethyl-N-(4-bromo-phenyl)-amine
T2 - Structural studies and anticancer activity
AU - Abdel Ghani, Nour T.
AU - Mansour, Ahmed M.
PY - 2012/1
Y1 - 2012/1
N2 - [MLCl 2] (L = (1H-benzimidazol-2-ylmethyl)-N-(4-bromo-phenyl)- amine; M = Pd & Pt) and [PdL(OH 2) 2]2XzH 2O (X = Br, I, z = 2; X = SCN, z = 1; X = NO 3, z = 0) complexes have been synthesized as potential anticancer compounds and their structures were elucidated using elemental analysis, spectral, thermal analysis and X-ray powder diffraction. The benzimidazole (L) crystallizes in the space group P2 1/c with a = 8.6660(3) , b = 16.6739(7) , c = 9.8611(4) and β = 113.505(3) ° and forms an infinite chain structure with a trans-zigzag type along the crystallographic axis "a", through the intermolecular H-bond. FT-IR and 1H NMR studies revealed that the ligand L is coordinated to the metal ion via the pyridine-type nitrogen (N py) of the benzimidazole ring and secondary amino group (NH sec). Quantum mechanical calculations of energies, geometries, vibrational wavenumbers, and 1H NMR of the benzimidazole L and its complexes were carried out by DFT/B3LYP method combined with 6-31G(d) and LANL2DZ basis sets. Natural bond orbital (NBO) analysis and frontier molecular orbitals (FMO) were performed at B3LYP/LANL2DZ level of theory. The benzimidazole L, in comparison to its metal complexes was screened for its antibacterial activity. The complexes showed cyctotoxic effects against human breast cancer (MCF7), hepatocarcinoma (HepG 2) and colon carcinoma cells (HCT). The platinum complex (6) exhibited a moderate antitumor activity against MCF7 with IC 50 = 10.2 μM comparing to that reported for cis-platin 9.91 μM.
AB - [MLCl 2] (L = (1H-benzimidazol-2-ylmethyl)-N-(4-bromo-phenyl)- amine; M = Pd & Pt) and [PdL(OH 2) 2]2XzH 2O (X = Br, I, z = 2; X = SCN, z = 1; X = NO 3, z = 0) complexes have been synthesized as potential anticancer compounds and their structures were elucidated using elemental analysis, spectral, thermal analysis and X-ray powder diffraction. The benzimidazole (L) crystallizes in the space group P2 1/c with a = 8.6660(3) , b = 16.6739(7) , c = 9.8611(4) and β = 113.505(3) ° and forms an infinite chain structure with a trans-zigzag type along the crystallographic axis "a", through the intermolecular H-bond. FT-IR and 1H NMR studies revealed that the ligand L is coordinated to the metal ion via the pyridine-type nitrogen (N py) of the benzimidazole ring and secondary amino group (NH sec). Quantum mechanical calculations of energies, geometries, vibrational wavenumbers, and 1H NMR of the benzimidazole L and its complexes were carried out by DFT/B3LYP method combined with 6-31G(d) and LANL2DZ basis sets. Natural bond orbital (NBO) analysis and frontier molecular orbitals (FMO) were performed at B3LYP/LANL2DZ level of theory. The benzimidazole L, in comparison to its metal complexes was screened for its antibacterial activity. The complexes showed cyctotoxic effects against human breast cancer (MCF7), hepatocarcinoma (HepG 2) and colon carcinoma cells (HCT). The platinum complex (6) exhibited a moderate antitumor activity against MCF7 with IC 50 = 10.2 μM comparing to that reported for cis-platin 9.91 μM.
KW - Benzimidazole
KW - Biological activity
KW - DFT
KW - LANL2DZ
KW - NBO
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U2 - 10.1016/j.ejmech.2011.11.008
DO - 10.1016/j.ejmech.2011.11.008
M3 - Article
C2 - 22119126
AN - SCOPUS:84855821171
SN - 0223-5234
VL - 47
SP - 399
EP - 411
JO - European Journal of Medicinal Chemistry
JF - European Journal of Medicinal Chemistry
IS - 1
ER -
