269-07-8Relevant articles and documents
Inhibitors of Hepatic Mixed-Function Oxidases. 4. Effects of Benzimidazole and Related Compounds on Aryl Hydrocarbon Hydroxylase Activity from Phenobarbitone and 3-Methylcholanthrene Induced Rats
Little, Peter J.,Ryan, Adrian J.
, p. 622 - 626 (1982)
A series of 2-n-alkylbenzimidazoles inhibited cytochrome P-450 dependent aryl hydrocarbon hydroxylase (AHH) and aminopyrine N-demethylase (ADPM) activities in phenylbarbitone (PB) induced rat liver microsomes. 2-Undecylbenzimidazole was the most potent compound in the series, having I50 values of 1.8E-5 and 1.5E-5 M against AHH and APDM activities, respectively.Inhibitory activity increased with increasing carbon chain length of the 2-substituent.Regression analysis showed that there was an apparent relationship between inhibitory activity and hydrophobicity (expressed as the octanol/water partition coefficient) for the inhibition of both AHH and APDM activities in PB-induced rat liver, microsomes.In contrast, these compounds showed little or no inhibitory activity toward cytochrome P-448 dependent AHH activity in hepatic microsomes from 3-methylcholanthrene (3-MC) treated rats.Two 5,6-dimethylbenzimidazoles showed slight inhibitory activity and naphthoimidazole was only threefold less active toward 3-MC-induced (I50 = 2.6E-4 M) than PB-induced (I50 = 8.4E-5) AHH activity.These results suggest that for nitrogen heterocycles there may be a relationship of increasing polycyclic size and increasing inhibitory activity toward AHH activity in 3-MC-induced rat liver microsomes.
Selective CO2 adsorption and Lewis acid catalytic activity towards naphthimidazole synthesis by a Zn-MOF
Agarwal, Rashmi A.,De, Dinesh
, (2020)
A two-fold interpenetrated, three dimensional Zn-based porous MOF, {[Zn(BPBA)Cl]?5H2O}n (1) [BPBA = 3,5-bis-(4-oxo-4H-pyridin-1-yl)-benzoate], has been synthesized at high temperature under solvothermal conditions by the in situ acidic hydrolysis of the tripodal ligand 3,5-bis-(4-oxo-4H-pyridin-1-yl)-benzonitrile (BPBN). The de-solvated MOF exhibited selective CO2 adsorption at a temperature of 195 K and 1 bar pressure over N2 and H2. Interestingly, the four coordinated Zn(II) sites in the MOF exhibited high Lewis acidic heterogeneous catalytic activity for the synthesis of naphthimidazole in excellent yield without pre-activation of the MOF. The Zn(II) sites could directly coordinate to the substrate to catalyze the chemical transformation by an expansion of the coordination number. The π-π supramolecular interactions between the aromatic rings of the framework and the substrate molecule might help in the substrate activation.
In-Gene Quantification of O6-Methylguanine with Elongated Nucleoside Analogues on Gold Nanoprobes
Trantakis, Ioannis A.,Nilforoushan, Arman,Dahlmann, Heidi A.,St?uble, Celine K.,Sturla, Shana J.
, p. 8497 - 8504 (2016)
Exposure of DNA to chemicals can result in the formation of DNA adducts, a molecular initiating event in genotoxin-induced carcinogenesis. O6-Methylguanine (O6-MeG) is a highly mutagenic DNA adduct that forms in human genomic DNA upon reaction with methylating agents of dietary, environmental, or endogenous origin. In this work, we report the design and synthesis of novel non-natural nucleoside analogues 1′-β-[1-naphtho[2,3-d]imidazol-2(3H)-one)]-2′-deoxy-d-ribofuranose and 1′-β-[1-naphtho[2,3-d]imidazole]-2′-deoxy-d-ribofuranose and their use for quantifying O6-MeG within mutational hotspots of the human KRAS gene. The novel nucleoside analogues were incorporated into oligonucleotides conjugated to gold nanoparticles to comprise a DNA hybridization probe system for detecting O6-MeG in a sequence-specific manner on the basis of colorimetric readout of the nanoparticles. The concept described herein is unique in utilizing new nucleoside analogues with elongated hydrophobic surfaces to successfully measure in-gene abundance of O6-MeG in mixtures with competing unmodified DNA.
A ratiometric fluorescent probe for fluoride ion based on naphthoimidazolium receptor
Zou, Chunyan,Qiao, Qinglong,Zhao, Miao,Mao, Deqi,Wang, Danfeng,Feng, Lei,Cui, Jingnan,Xu, Zhaochao
, p. 43746 - 43751 (2014)
Three imidazolium derivatives 3-5 were designed and synthesized, in which naphthaimidazolium group acted as both fluorophore and anion receptor. Compound 3 exhibited high selectivity for F- in CH3CN solution over all the other anions and acted as a ratiometric fluorescent probe for F- with an enhanced blue-shift in emission. However, the fluorescence of compound 4 and 5 displayed a quenched blue-shift in emission with fluoride ion and could be quenched by some other tested anions, where the degree of quenching depended on the characteristic of the anions. More importantly, only compound 3 could detect F- in DMSO-water (955, v/v) aqueous solution ratiometrically. Based on the analysis of the results of 1H-NMR and 19F-NMR, it was deduced that compound 3 bound with F- mainly by the force of hydrogen bonding, while compound 4 and 5 coordinated with F- through electrostatic interaction. This journal is
Endoplasmic Reticulum-Targeted Ratiometric N-Heterocyclic Carbene Borane Probe for Two-Photon Microscopic Imaging of Hypochlorous Acid
Pak, Yen Leng,Park, Sang Jun,Song, Gyeongok,Yim, Yubin,Kang, Hyuk,Kim, Hwan Myung,Bouffard, Jean,Yoon, Juyoung
, p. 12937 - 12943 (2018)
The naphthoimidazolium borane 4 is shown to be a selective probe for HOCl over other reactive oxygen species. Unlike other boronate-reactive oxygen species (ROS) fluorogenic probes that are oxidized by HOCl through a nucleophilic borono-Dakin oxidation mechanism, probe 4 is distinguished by its electrophilic oxidation mechanism involving B-H bond cleavage. Two-photon microscopy experiments in living cells and tissues with the probe 4 demonstrate the monitoring of endogenous HOCl generation and changes in HOCl concentrations generated in the endoplasmic reticulum during oxidative stress situations.
Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical
Deng, Guo-Jun,Fu, Mei,Huang, Huawen,Ji, Xiaochen,Li, Yongtong
supporting information, p. 5594 - 5598 (2020/09/21)
A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.
Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones
Huang, Hsin-Yi,Liang, Chien-Fu,Lin, Xiu-Yi,Yen, Shih-Yao
supporting information, p. 5726 - 5733 (2020/08/21)
N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.
In Situ Formation of Frustrated Lewis Pairs in a Water-Tolerant Metal-Organic Framework for the Transformation of CO2
Shyshkanov, Serhii,Nguyen, Tu N.,Ebrahim, Fatmah Mish,Stylianou, Kyriakos C.,Dyson, Paul J.
supporting information, p. 5371 - 5375 (2019/03/17)
Frustrated Lewis pairs (FLPs) consist of sterically hindered Lewis acids and Lewis bases, which provide high catalytic activity towards non-metal-mediated activation of “inert” small molecules, including CO2 among others. One critical issue of homogeneous FLPs, however, is their instability upon recycling, leading to catalytic deactivation. Herein, we provide a solution to this issue by incorporating a bulky Lewis acid-functionalized ligand into a water-tolerant metal-organic framework (MOF), named SION-105, and employing Lewis basic diamine substrates for the in situ formation of FLPs within the MOF. Using CO2 as a C1-feedstock, this combination allows for the efficient transformation of a variety of diamine substrates into benzimidazoles. SION-105 can be easily recycled by washing with MeOH and reused multiple times without losing its identity and catalytic activity, highlighting the advantage of the MOF approach in FLP chemistry.
Cobalt-catalyzed synthesis of N-containing heterocycles: Via cyclization of ortho -substituted anilines with CO2/H2
Ke, Zhengang,Yu, Bo,Wang, Huan,Xiang, Junfeng,Han, Juanjuan,Wu, Yunyan,Liu, Zhenghui,Yang, Peng,Liu, Zhimin
, p. 1695 - 1701 (2019/04/10)
The CO2-involved synthesis of chemicals is of great significance from the green and sustainable chemistry viewpoint. Herein, we report a non-noble metal catalytic system composed of CoF2, CsF and P(CH2CH2PPh2)3 (denoted as PP3) for the synthesis of N-containing heterocycles from ortho-substituted anilines and CO2/H2. Mechanism investigation indicates that [Co(PP3)H(CO2)]+ is a catalytically active intermediate under working conditions; and CsF plays important roles in activating ortho-substituted anilines via hydrogen bond interactions, thus promoting the formation of the final products. This catalytic system is highly efficient, and allows a wide scope of ortho-substituted anilines, together with excellent functional group tolerance, affording various N-containing heterocycles in good to excellent yields.
A benzimidazole and synthetic method of derivative thereof (by machine translation)
-
Paragraph 0040; 0042; 0050; 0051, (2019/02/10)
The present invention provides a benzimidazole and its derivative synthesis method, the method through the imidazole chloride catalyzed O-phenylenediamine cyclized, realizes the multi-functional chain dibasic and imidazole and 2 - substituted benzimidazole synthesis, method is simple and economic, and the practicability is strong. This invention does not have any other catalyst or additive, synthetic method has good functional group tolerance and excellent yield and purity, reaction time is short, and does not need the harsh reaction conditions, is suitable for industrial production. (by machine translation)
