Design, Synthesis, Characterization and Anticancer Evaluation of Novel Mixed Complexes Derived from 2-(1H-Benzimizadol-2-yl)aniline Schiff base and 2-Mercaptobenzimidazole or 2-Aminobenzothiazole

Abstract

Two Schiff base ligands ((benzimidazol-2-phenyl)iminomethyl)phenol (HL1) (1) and 2-(1-H-benzimidazol-2yl)phenyl)imino)methyl) naphthol (HL2) (2) were synthesized via condensation of 2-(1H-benzimizadol-2-yl)aniline and respectively salicylaldehyde or naphtylaldehyde. The synthesis of mixed complexes (3)-(6) was realized by reacting ligands HL1 (1) and HL2 (2), copper salt (CuCl2.2H2O) and respectively one equivalent of 2-mercaptobenzothiazole or 2aminobenzothiazole. The ligands as well as the metal complexes have been identified with multiple spectroscopic techniques. The results data indicate that the copper is linked to ligands via deprotonated phenolic oxygen atom, nitrogen or sulphur atom of co-ligands and the coordination was realized through the azomethine group. X-ray powder diffraction analysis of complexes suggests that they posses monoclinic structure for complexes (3) and (4), while complex (5) has orthorhombic structure and rhombohedral structure for complex (6). The in vitro anticancer activities of the different complexes were evaluated and the results revealed an important cytotoxicity of complex (6) against lung human cancer A-549 and very good selectivity with 12.4 values of inhibitory concentration IC 50. The best result was described with complex (4) and present high activities on both A-549 and Caco-2 indicating good selectivity on lung human cancer A-549 and moderate selectivity on colorectal cell line Caco-2 with 10.9 and 15.7 respectively of IC 50.

Synthesis, Molecular Docking, and Bioactivity Study of Novel Hybrid Benzimidazole Urea Derivatives: A Promising α-Amylase and α-Glucosidase Inhibitor Candidate with Antioxidant Activity

“…The discovery of new α-glucosidase and α-amylase inhibitor agents is an interesting method of obtaining such drugs. To contribute to the advancement of the design and the discovery of new bioactive species [ 66 , 67 , 68 , 69 , 70 , 71 ], we combined the two patterns, benzimidazole and urea, in the same molecule, allowing for potential antidiabetic agents, and having good anti-oxidant activity.…”

Synthesis and Structural Characterization of Palladium(II) Mixed-Ligand Complexes of N-(Benzothiazol-2-yl)benzamide and 1,2-Bis(diphenylphosphino)ethane

“…7 The importance of benzothiazoles as ligands is increased through benzothiazole derivatives containing additional donor atoms, such as nitrogen, sulfur, or oxygen, that can coordinate bidentately through two nitrogen atoms 8,9 or nitrogen and oxygen atoms. 10 The different coordination methods adopted by benzothiazole derivatives result from the diversity of uses of the complexes of these derivatives in the biological field; benzothiazole derivatives and their complexes show different biological activities, such as antimicrobial activity, 11 antitumor activity, 12,13 inhibition of enzymes 14 and Alzheimer's disease, 15 and cytotoxic activity. 16 Metal complexes with heterocyclic ligands containing heteroatoms, such as nitrogen, sulfur, or oxygen, are of interest as simple structural models of more complex biological systems.…”

“…17 Transition-metal ions also play a vital role in biological processes and can form complexes with benzothiazole derivatives that exhibit enhanced biological activity. Benzothiazoles with a benzoylamino moiety substituted at the 2 position have a variety of biological properties, including antitumor 18 and antibacterial 13 properties. Because the coordination chemistry of N-(1,3-benzothiazol-2-yl)benzamide (HL) has not been extensively studied, the aim of the current study was to increase our understanding of HL coordination chemistry with palladium.…”

“…The different coordination methods adopted by benzothiazole derivatives result from the diversity of uses of the complexes of these derivatives in the biological field; benzothiazole derivatives and their complexes show different biological activities, such as antimicrobial activity, antitumor activity, , inhibition of enzymes and Alzheimer’s disease, and cytotoxic activity . Metal complexes with heterocyclic ligands containing heteroatoms, such as nitrogen, sulfur, or oxygen, are of interest as simple structural models of more complex biological systems .…”

Design, synthesis, biological evaluation, and in silico studies of 2‐aminobenzothiazole derivatives as potent PI3Kα inhibitors

“…Recently, aminobenzothiazole has gained significant attention due to its pharmacological activity, including anti-inflammatory, antifungal, anticonvulsant, analgesics, and anticancer activity. [4][5][6][7][8][9] It is reported that nitrogen-containing heterocyclic rings like aminobenzothiazole offer a polarized character, which plays a significant role in the stability of the molecule-receptor complex. It generally increases the complex stability by establishing an optimum interaction that produces anticancer effects.…”