- 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
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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.
- Little, Peter J.,Ryan, Adrian J.
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- Selective CO2 adsorption and Lewis acid catalytic activity towards naphthimidazole synthesis by a Zn-MOF
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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.
- Agarwal, Rashmi A.,De, Dinesh
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- In-Gene Quantification of O6-Methylguanine with Elongated Nucleoside Analogues on Gold Nanoprobes
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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.
- Trantakis, Ioannis A.,Nilforoushan, Arman,Dahlmann, Heidi A.,St?uble, Celine K.,Sturla, Shana J.
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- A ratiometric fluorescent probe for fluoride ion based on naphthoimidazolium receptor
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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
- Zou, Chunyan,Qiao, Qinglong,Zhao, Miao,Mao, Deqi,Wang, Danfeng,Feng, Lei,Cui, Jingnan,Xu, Zhaochao
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- Endoplasmic Reticulum-Targeted Ratiometric N-Heterocyclic Carbene Borane Probe for Two-Photon Microscopic Imaging of Hypochlorous Acid
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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.
- Pak, Yen Leng,Park, Sang Jun,Song, Gyeongok,Yim, Yubin,Kang, Hyuk,Kim, Hwan Myung,Bouffard, Jean,Yoon, Juyoung
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- Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical
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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.
- Deng, Guo-Jun,Fu, Mei,Huang, Huawen,Ji, Xiaochen,Li, Yongtong
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supporting information
p. 5594 - 5598
(2020/09/21)
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- Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones
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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.
- Huang, Hsin-Yi,Liang, Chien-Fu,Lin, Xiu-Yi,Yen, Shih-Yao
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supporting information
p. 5726 - 5733
(2020/08/21)
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- In Situ Formation of Frustrated Lewis Pairs in a Water-Tolerant Metal-Organic Framework for the Transformation of CO2
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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.
- Shyshkanov, Serhii,Nguyen, Tu N.,Ebrahim, Fatmah Mish,Stylianou, Kyriakos C.,Dyson, Paul J.
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supporting information
p. 5371 - 5375
(2019/03/17)
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- Cobalt-catalyzed synthesis of N-containing heterocycles: Via cyclization of ortho -substituted anilines with CO2/H2
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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.
- Ke, Zhengang,Yu, Bo,Wang, Huan,Xiang, Junfeng,Han, Juanjuan,Wu, Yunyan,Liu, Zhenghui,Yang, Peng,Liu, Zhimin
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p. 1695 - 1701
(2019/04/10)
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- A benzimidazole and synthetic method of derivative thereof (by machine translation)
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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)
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Paragraph 0040; 0042; 0050; 0051
(2019/02/10)
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- Imidazolium chloride-catalyzed synthesis of benzimidazoles and 2-substituted benzimidazoles from o-phenylenediamines and DMF derivatives
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A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields.
- Gan, Zongjie,Tian, Qingqiang,Shang, Suqin,Luo, Wen,Dai, Zeshu,Wang, Huajun,Li, Dan,Wang, Xuetong,Yuan, Jianyong
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p. 7450 - 7456
(2018/11/27)
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- Carbon Dioxide Mediated Novel Synthesis of Quinazoline-2,4(1H,3H)-dione in Water
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A novel, efficient, and scalable CO2 mediated synthesis of quinazoline-2,4(1H,3H)-dione was developed by a simple cyclization of 2-aminobenzonitrile with DMF in water as the solvent. This is the first report of its kind. DMF was used as the necessary carbon source in the synthesis of quinazoline-2,4(1H,3H)-dione. This synthetic protocol is very efficient; it gives >99% conversion with excellent selectivity. The product was isolated by filtration because of the highly insoluble nature of quinazoline-2,4(1H,3H)-dione in water. The co-product, dimethyl amine, also has industrial importance, and the CO2 that is used can be recycled. This protocol has wide-spread applications in the syntheses of benzimidazole and benzothiazole.
- Rasal, Kalidas B.,Yadav, Ganapati D.
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p. 2067 - 2073
(2016/12/24)
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- Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst
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B(C6F5)3 combined with atmospheric CO2 was found to be highly effective for the cyclization of ortho-substituted aniline derivatives with N,N-dimethylformamide (DMF), and a series of N-containing heterocycles including benzothiazoles, benzimidazoles, quinazolinone and benzoxazole were obtained in good to excellent yields.
- Gao, Xiang,Yu, Bo,Mei, Qingqing,Yang, Zhenzhen,Zhao, Yanfei,Zhang, Hongye,Hao, Leiduan,Liu, Zhimin
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p. 8282 - 8287
(2016/10/11)
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- Method For Preparing Nitrogen Compounds
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The present invention relates to a method for preparing nitrogen compounds using carbon dioxide, and to the use of the method in the production of vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides, herbicides, antifungal agents and fertilisers. The invention also relates to a method for producing vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides, herbicides, antifungal agents and fertilisers, which includes a step of preparing nitrogen compounds using the method of the invention. The invention further relates to a method for preparing labelled nitrogen compounds using carbon dioxide and to the uses thereof.
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Paragraph 0192; 0193
(2015/06/03)
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- BASE-MODIFIED-NUCLEOSIDE ANALOGS FOR THE DETECTION OF O6-ALKYL GUANINE
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The present disclosure provides novel compounds containing a base- modified nucleoside of formula and methods for detecting the presence of guanine in a nucleic acid and for isolating O6-alkyl guanine comprising nucleic acid. The disclosure is based on base-modified-nucleoside analogs that form stable base pairs with O6-alkyl guanine.
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Page/Page column 32
(2015/11/10)
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- N-Substituted Formamides as C1-Sources for the Synthesis of Benzimidazole and Benzothiazole Derivatives by Using Zinc Catalysts
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An efficient and convenient one-pot protocol has been developed for the synthesis of a variety of benzimidazole, benzoxazole, and benzothiazole derivatives. This novel approach uses various o-phenylenediamines and N-substituted formamides (C1 sources) in a zinc-catalyzed cyclization in the presence of poly(methylhydrosiloxane) to afford the corresponding derivatives as sole products in moderate to excellent yields.
- Nale, Deepak B.,Bhanage, Bhalchandra M.
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p. 2835 - 2842
(2015/12/18)
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- Tunable anisotropic thermal expansion of a porous zinc(II) metal-organic framework
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A novel three-dimensional metal-organic framework (MOF) that displays anisotropic thermal expansion has been prepared and characterized by single-crystal X-ray diffraction (SCD) and thermal analysis. The as-prepared MOF has one-dimensional channels containing guest molecules that can be removed and/or exchanged for other guest molecules in a single-crystal to single-crystal fashion. When the original guest molecules are replaced there is a noticeable effect on the host mechanics, altering the thermal expansion properties of the material. This study of the thermal expansion coefficients of different inclusion complexes of the host MOF involved systematic alteration of guest size, i.e., methanol, ethanol, n-propanol, and isopropanol, showing that fine control over the thermal expansion coefficients can be achieved and that the coefficients can be correlated with the size of the guest. As a proof of concept, this study demonstrates the realizable principle that a single-crystal material with an exchangeable guest component (as opposed to a composite) may be used to achieve a tunable thermal expansion coefficient. In addition, this study demonstrates that greater variance in the absolute dimensions of a crystal can be achieved when one has two variables that affect it, i.e., the host-guest interactions and temperature.
- Grobler, Ilne,Smith, Vincent J.,Bhatt, Prashant M.,Herbert, Simon A.,Barbour, Leonard J.
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supporting information
p. 6411 - 6414
(2013/06/05)
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- Ratiometric fluorescence sensing of fluoride ions by an asymmetric bidentate receptor containing a boronic acid and imidazolium group
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The synthesis of the first examples of aoion receptors that utilize boron-fluoride interactions and (C-H)+-F~-t:ype ionic hydrogen-bond interactions in. the binding of F ions is reported herein, o-, m-, and p-Phenylboronic acids were linked to
- Xu, Zhaochao,Kim, Sook Kyung,Han, Su Jung,Lee, Chongmok,Kociok-Kohn, Gabriele,James, Tony D.,Yoon, Juyoung
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body text
p. 3058 - 3065
(2009/12/01)
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- Src kinase inhibitor compounds
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Pyrimidine compounds (Formula I), or their pharmaceutically acceptable salts, hydrates, solvates, crystal forms and individual diastereomers, and pharmaceutical compositions including the same, which are inhibitors of tyrosine kinase enzymes, and as such are useful in the prophylaxis and treatment of protein tyrosine kinase-associated disorders, such as immune diseases, hyperproliferative disorders and other diseases in which inappropriate protein kinase action is believed to play a role, such as cancer, angiogensis, atheroscelerosis, graft rejection, rheumatoid arthritis and psoriasis.
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- Novel Desulphurization of Thiourea Derivatives by Alkaline Autoxidation
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Autoxidation of 1,3-disubstituted thioureas in the presence of oxygen and tertiary butoxide in tertiary butanol afforded the corresponding ureas in good yields together with small amounts of the corresponding guanidines while the same treatment of benz- or naphth-imidazole-2-thiones gave the parent imidazoles and the 2-sulphonic acids.
- Kim, Yong Hae,Kim, Hyung Jin,Yon, Gyu Hwan
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p. 1064 - 1065
(2007/10/02)
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- Naphth[2,3-d]imidazoles
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Imidazole derivatives of the formula STR1 wherein R1, R2, R3 R4, R5, X and n are as hereinafter set forth, and pharmaceutically acceptable acid addition salts thereof, are described. The compounds of formula I are useful in the treatment of gastric ulcers.
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