Eight new ruthenium(II) complexes of ,-chelating pyrazolylbenzimidazole ligands of the general formula [Ru(-cym)(L)X] [where the ligand L is 2-(1-pyrazol-1-yl)-1-benzo[]imidazole () substituted at the 4 position of the pyrazole ring by Cl (), Br (), or I () and X = Cl and I] were synthesized and characterized using various analytical techniques. Complexes and were also characterized by single-crystal X-ray crystallography, and they crystallized as a monoclinic crystal system in space groups 2/ and 2/, respectively. The complexes display good solution stability at physiological pH 7.4. The iodido-coordinated pyrazolylbenzimidazole ruthenium(II) -cymene complexes (, , , and ) are more resistant toward hydrolysis and have less tendency to form monoaquated complexes in comparison to their chlorido analogues (, , , and ). The halido-substituted 2-(1-pyrazol-1-yl)-1-benzo[]imidazole ligands, designed as organic-directing molecules, inhibit vascular endothelial growth factor receptor 2 (VEGFR2) phosphorylation. In addition, the ruthenium(II) complexes display a potential to bind to DNA bases. The cytotoxicity profile of the complexes (IC ca. 9-12 μM for -) against the triple-negative breast cancer cells (MDA-MB-231) show that most of the complexes are efficient. The lipophilicity and cellular accumulation data of the complexes show a good correlation with the cytotoxicity profile of -. The representative complexes and demonstrate the capability of arresting the cell cycle in the G2/M phase and induce apoptosis. The inhibition of VEGFR2 phosphorylation with the representative ligands and and the corresponding metal complexes and shows that the organic-directing ligands and their complexes inhibit VEGFR2 phosphorylation. Besides, , , , and inhibit the phosphorylation of extracellular signal-regulated kinase 1/2 (ERK1/2) and proto-oncogene tyrosine-protein kinase (Src), capable of acting downstream of VEGFR2 as well as independently. Compounds , , , and have a lesser effect on ERK1/2 and more prominently affect Src phosphorylation. We extended the study for and in the Tg(fli1:gfp) zebrafish model and found that is more effective compared to in inhibiting angiogenesis.