Synthesis of new 1,2,3-triazole linked benzimidazole molecules as anti-proliferative agents

A Facially Coordinating Tris-Benzimidazole Ligand for Nonheme Iron Enzyme Models

“…20 In contrast, when the ratio is less than 2:1, a broad signal is apparent at −73 ppm indicative of an equilibrium between bound and unbound triflate ions in solution implicating the presence of monoligated species [4] + ( Figure S12). This is consistent with a Schlenk equilibrium between [3] 2+ and [4] + at room temperature in MeCN; using density functional theory (DFT), the calculated equilibrium lies toward the bis ligated complex with a free energy of -3.2 kcal/mol (see SI). 1 H NMR spectroscopy was used to construct a kind of "Job plot" to determine the optimal ratio of Fe(OTf)2:Tbim to prepare in situ [4] + for the catalysis studies later ( Figure S17), and a Fe(OTf)2:Tbim stoichiometry of 3:2 was the optimal ratio to achieve the highest concentration of [4] + in the 10 mM regime.…”

“…Specifically, we obtained diethyl 2-hydroxy-2-phenylmalonate (HOPhmal) as the major product following the literature method (Table 1). 17 Nearly identical results were obtained when [Phmal]oxidations were repeated using [4] + , [3] 2+ , and Fe(OTf)2 ( Table 1). In the absence of catalyst, or if water was not rigorously excluded, the HPhmal or HOPhmal was obtained as the major product.…”

“…Once the solution became homogenous, the solvent was removed in vacuo and the resulting residue was taken up in 5 mL of methanol. The solution was stirred with NaBPh4 (16 mg, 0.046 mmol) and a yellow solid formed that was isolated by filtration and redissolved in a minimum amount of dichloromethane from which crystalline [3][BPh4]2 precipitated over 24 hours (18.2 mg, 98% yield). ( Figure S16) ATR-FTIR (cm - The following procedures are nearly identical, but differ slightly in workup.…”

“…For instance, histidine donors are imidazole nitrogen groups with sp 2 hybridization and in an aromatic ring. In contrast, tacn has sp 3 hybridization and is not conjugated. Accordingly, we noted that Gebbink and coworkers modeled the 2-His-1-C facial triad using imidazole and benzimidazole ligands Natural two-histidine one-carboxylate enzyme binding site (left) compared to tridentate ligands with representative "mono-dentate" ligand donor groups and their respective [NH] + pKa in water (see Fig.…”

Design and preparation of [4,4′-bipyridine]-1,1′-diium trinitromethanide (BPDTNM) as a novel nanosized ionic liquid catalyst: application to the synthesis of 1-(benzoimidazolylamino)methyl-2-naphthols

“…Benzimidazole derivatives are interesting heterocyclic compounds which are present in a wide variety of biologically active natural products [1][2][3]. Some important benzimidazole-derivatives such as, omeprazole, timoprazole, DMA, telmisartan, rabeprazole, and thiabendazole [4,5] have been recently shown as important and renowned marketed drugs with antibacterial and anthelminthic activities, among others.…”