4856-97-7Relevant articles and documents
The construction of coordination networks based on imidazole-based dicarboxylate ligand containing hydroxymethyl group
Zheng, Sheng-Run,Cai, Song-Liang,Pan, Mei,Fan, Jun,Xiao, Tian-Tian,Zhang, Wei-Guang
, p. 883 - 888 (2011)
Reaction of Cd(ii), Fe(ii), and Cu(ii) with a new ligand 2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylic acid (H4hmIDC) and 4,4′-bipyridine (bpy) affords three coordination polymers of {[Cd(H 2hmIDC)(bpy)]·0.5bpy·H2O}n (1), [Fe2(HhmIDC)2]n (2), and {[Cu 2(ITC)(bpy)(H2O)3]·2.5H 2O}n (3) (ITC = imidazole-2,4,5-tricarboxylic acid), respectively. Complex 1 and complex 3 are (4,4) nets in topological view and display in different packing mode, while hydroxymethyl group in complex 3 is oxidized to carboxylic group in situ. Complex 2 is a rare example of a cdl-e network containing both tetrahedral and square nodes. The hydroxymethyl groups act as a precursor and undergo different reactions directed by metal ions.
Cobalt(II) complexes based on (1-methyl-1H-benzo[d]imidazol-2-yl) methanol derivative: synthesis, crystal structure, spectroscopy, DFT calculations, and antioxidant activity
Benhassine, Anfel,Boulebd, Houssem,Anak, Barkahem,Bouraiou, Abdelmalek,Bouacida, Sofiane,Bencharif, Mustapha,Belfaitah, Ali
, p. 311 - 328 (2018)
In this paper, we present a combined experimental and computational study of two new cobalt(II) complexes as [Co(Hmbm)2(OAc)2] and [Co(Hmbm)2(H2O)2]Cl2 (Hmbm = (1-methyl-1H-benzo[d]imidazol-2-yl)methanol). Both complexes were characterized by FT-IR and UV–vis spectroscopy, elemental analysis, and single-crystal X-ray crystallography. The molecular geometries, electronic transitions, and vibrational frequencies of the two complexes and the ligand (Hmbm) in the ground state have been calculated using global hybrid (B3LYP) and range-separated hybrid (CAM-B3LYP) density functional. Qualitative description of excited states and charge transfer character of electronic transitions states were carried out by plotting the Natural Transition Orbitals (NTOs) for main states, and were assigned to LMCT. The ligand and its Co(II) complexes have been evaluated for their potential as DPPH radical scavengers.
One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles
Guo, Tao,He, Jianghua,Liu, Tianwei,Zhang, Yuetao
supporting information, (2022/02/07)
It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.
Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon
Raja, Dineshkumar,Philips, Abigail,Sundaramurthy, Devikala,Chandru Senadi, Gopal
, p. 3754 - 3759 (2021/10/14)
D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.
Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2
Maciejewska, Agnieszka Monika,Paprocki, Daniel,Poznański, Jaros?aw,Speina, El?bieta,Winiewska‐szajewska, Maria
supporting information, (2021/06/09)
Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.