615-16-7Relevant articles and documents
Synthesis of bis(2-imino-1,3-dimethylbenzimidazoline)s via reactions of a solvothermally prepared benzimidazolium chloride and diamines
Zuo, Shengli,Zhang, Fan,Liu, Jianjun,Zuo, Ang
, (2021)
The first solvothermal preparation of benzimidazolium chloride for the synthesis of bis(2-imino-1,3-dimethylbenzimidazoline) derivatives from readily available diamines is reported, including an optimized preparation of previously reported solvothermal synthesis of the benzimidazolium intermediate. Several primary diamines including both aliphatic and aromatic linkers were converted to the corresponding bis(guanidine)s in moderate to good yield.
Preparation of 2(3H)-benzimidazolone and its derivative under aqueous condition as a potential agent for antidiabetic compounds
Abbas, Muhammad Azhar,Hameed, Shahid,Kressler, Joerg
, p. 509 - 511 (2013)
A focused library of 2(3H)-benzimidazolone and its derivatives has been synthesized in an attempt to identify their antidiabetic potential. All the products have been synthesized under aqueous conditions in lesser time with better yield and purity. A new effective and convenient method for in situ synthesis of five member heterocyclic ring by reaction of phenylene diamine with urea in solvent phase. All the synthesized compounds were characterized by modern spectroscopic techniques.
Indium(III)-Catalyzed Synthesis of Primary Carbamates and N-Substituted Ureas
Jain, Isha,Malik, Payal
supporting information, p. 93 - 97 (2021/11/26)
An indium triflate-catalyzed synthesis of primary carbamates from alcohols and urea as an ecofriendly carbonyl source has been developed. Various linear, branched, and cyclic alcohols were converted into the corresponding carbamates in good to excellent yields. This method also provided access to N-substituted ureas by carbamoylation of amines. All the products were obtained by simple filtration or crystallization, without the need for chromatographic purification. Mechanistic investigations suggest that the carbamoylation reaction proceeds through activation of urea by O-coordination with indium, followed by nucleophilic attack by the alcohol or amine on the carbonyl center of urea. The inexpensive and easily available starting materials and catalyst, the short reaction times, and the ease of product isolation highlight the inherent practicality of the developed method.
PrVO4/SnD NPs as a Nanocatalyst for Carbon Dioxide Fixation to Synthesis Benzimidazoles and 2-Oxazolidinones
He, Zemin,Yu, Ping,Zhao, Yuzhen,Zhang, Huimin,Zhang, Yongming,Kang, Xiaoxi,Zhang, Haiquan,Sadeghzadeh, Seyed Mohsen
, p. 1623 - 1632 (2020/10/19)
Recently CO2 stabilization has received a great deal of attention because of its probable applications as a rich C1 resource and the synthesis of several fine chemicals can be accomplished through this stabilization. In this study, Sn(IV) doping dendritic fibrous nanosilica (SnD) supported PrVO4 nanoparticles as a catalyst (PrVO4/SnD) was synthesized by a in-situ procedure. The SnD with the ratios of Si/Sn in a variety of 6 to 40 were acquired through direct hydrothermal synthesis (DHS), and PrVO4 NPs on the surfaces of SnD were reduced in-situ. X-Ray diffraction (XRD), Scanning electron microscope (SEM), Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), and X-ray energy dispersive spectroscopy (EDS) were deployed for identifying the PrVO4/SnD. It is potentially a highly dynamic catalyst in the stabilization of CO2 for the production of 2-oxazolidinones and benzimidazoles. In addition, the catalyst is very easy to recycle and reuse without significant loss of active site Cu metal. Graphic Abstract: PrVO4/SnD NPs as a nanocatalyst for carbon dioxide fixation to synthesis benzimidazoles and 2-oxazolidinones. [Figure not available: see fulltext.]
CdSnO3/SnD NPs as a Nanocatalyst for Carbonylation of o-Phenylenediamine with CO2
Liu, Can,Sadeghzadeh, Seyed Mohsen
, p. 2807 - 2815 (2021/02/05)
In order to carbonize o-phenylenediamine with CO2, an effective approach was used with UV light irradiation by Sn(IV) doping DFNS (SnD) supported CdSnO3 as a catalyst (CdSnO3/SnD). In this catalyst, SnD with the ratios of Si/Sn in the range of 6 to 50 were obtained using the Direct Hydrothermal Synthesis (DHS), and the nanoparticles of CdSnO3 on the surfaces of SnD were reduced in situ. Scanning Electron Microscope (SEM), X-ray Diffraction (XRD), Fourier Transform Infrared Spectroscopy (FT-IR), X-ray Energy Dispersive Spectroscopy (EDS), and Transmission Electron Microscopy (TEM) were utilized for characterizing CdSnO3/SnD. It was found that CdSnO3/SnD nanostructures could be used for synthesizing o-phenylenediamines due to their effective and novel catalytic behavior through the reaction between o-phenylenediamines and CO2. Graphic Abstract: [Figure not available: see fulltext.]
Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis
Adamson, Christopher,Kajino, Hidetoshi,Kanai, Motomu,Kawashima, Shigehiro A.,Yamatsugu, Kenzo
supporting information, p. 14976 - 14980 (2021/09/29)
Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.
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.
Cytotoxic Ruthenium(II) Complexes of Pyrazolylbenzimidazole Ligands That Inhibit VEGFR2 Phosphorylation
Acharya, Moulinath,Chakraborty, Ayan,Chakraborty, Manas Pratim,Das, Rahul,Koley, Tuhin Subhra,Mukherjee, Arindam,Purkait, Kallol,Roy, Shantanu Saha,Roy, Souryadip
, p. 18379 - 18394 (2021/12/01)
Eight new ruthenium(II) complexes of N,N-chelating pyrazolylbenzimidazole ligands of the general formula [RuII(p-cym)(L)X]+ [where the ligand L is 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole (L1) substituted at the 4 position of the pyrazole ring by Cl (L2), Br (L3), or I (L4) and X = Cl- and I-] were synthesized and characterized using various analytical techniques. Complexes 1 and 3 were also characterized by single-crystal X-ray crystallography, and they crystallized as a monoclinic crystal system in space groups P21/n and P21/c, respectively. The complexes display good solution stability at physiological pH 7.4. The iodido-coordinated pyrazolylbenzimidazole ruthenium(II) p-cymene complexes (2, 4, 6, and 8) are more resistant toward hydrolysis and have less tendency to form monoaquated complexes in comparison to their chlorido analogues (1, 3, 5, and 7). The halido-substituted 2-(1H-pyrazol-1-yl)-1H-benzo[d]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 (IC50 ca. 9-12 μM for 4-8) 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 1-8. The representative complexes 3 and 7 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 L2 and L4 and the corresponding metal complexes 3 and 7 in vitro shows that the organic-directing ligands and their complexes inhibit VEGFR2 phosphorylation. Besides, L2, L4, 3, and 7 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 L2, L4, 3, and 7 have a lesser effect on ERK1/2 and more prominently affect Src phosphorylation. We extended the study for L2 and 3 in the Tg(fli1:gfp) zebrafish model and found that L2 is more effective in vivo compared to 3 in inhibiting angiogenesis.
Design, Synthesis, Cytotoxicity, and Molecular Docking Studies of New Benzimidazole Hybrids as Possible Anticancer Agents
Mishra, Shashank Shekher,Sharma, C. S.
, p. 21 - 29 (2021/08/12)
In the course of efforts to develop new anticancer agents, benzimidazole-based morpholine, thiomorpholine, and piperazine hybrid compounds were designed and synthesized. The structures of the synthesized compounds were confirmed by Proton nuclear magnetic resonance, Carbon-13 NMR, and mass spectroscopy. The title compounds were screened for cytotoxicity against breast and lung cancer cell lines. Compound 6c was found most active against lung cancer cell line with IC50 value of 2.11 μM and compound 10c was found most active against breast cancer cell line with IC50 of 2.23 μM. The molecular docking analysis was also carried out to explore binding pattern of compound with the target protein. All synthesized compounds showed excellent binding affinity toward target protein. Therefore, these findings will be helpful in future drug design of more potent anticancer agents.
Method for preparing carbonyl heterocyclic compound
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Paragraph 0036-0040, (2020/03/25)
The invention provides a method for preparing a carbonyl heterocyclic compound, wherein Lewis base and hydrosilane are used as accelerators and can efficiently enable an ortho-substituted aniline compound to react with normal-pressure CO2 to generate corresponding carbonyl heterocyclic compounds containing different functional groups under mild conditions (100 DEG C, digital). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of CO, high-pressure CO2 and noble metal catalysts is avoided, the intermediate isocyanate does not need to be purified and separated, the pure product can be obtained only through simple suction filtration and separation after the reaction is finished, and the synthetic method is efficient and universal, is suitable for preparing a series of benzimidazolone, benzoxazolone and benzothiazolone compounds and has high industrial application value.
