cas 1615-14-1, 1-(2-Hydroxyethyl)imidazole

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Easson,Pyman
p. 1806,1809
(1932)
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Structure-activity relationship modeling and experimental validation of the imidazolium and pyridinium based ionic liquids as potential antibacterials of mdr acinetobacter baumannii and staphylococcus aureus
Online Chemical Modeling Environment (OCHEM) was used for QSAR analysis of a set of ionic liquids (ILs) tested against multi-drug resistant (MDR) clinical isolate Acinetobacter baumannii and Staphylococcus aureus strains. The predictive accuracy of regression models has coefficient of determination q2 = 0.66 ? 0.79 with cross-validation and independent test sets. The models were used to screen a virtual chemical library of ILs, which was designed with targeted activity against MDR Acinetobacter baumannii and Staphylococcus aureus strains. Seven most promising ILs were selected, synthesized, and tested. Three ILs showed high activity against both these MDR clinical isolates.
Semenyuta, Ivan V.,Trush, Maria M.,Kovalishyn, Vasyl V.,Rogalsky, Sergiy P.,Hodyna, Diana M.,Karpov, Pavel,Xia, Zhonghua,Tetko, Igor V.,Metelytsia, Larisa O.
p. 1 - 15
(2021/01/14)

N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates
Abstract: The reactions of imidazoles with a series of dialkyl and alkylene carbonatesafforded the corresponding N-alkyl- andN-(hydroxyalkyl)imidazoles with highyields. The reactivity of dialkyl carbonates decreases in the series dimethyl> diethyl > dibutyl carbonate. Ethylene carbonate is a more efficientalkylating agent than trimethylene carbonate. The mechanisms of alkylation ofimidazole with dimethyl carbonate and ethylene carbonate were studied by DFTquantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory.
Gabov,Khamidullina,Puzyrev,Ezhikova,Kodess,Pestov
p. 2079 - 2086
(2021/02/09)

Polyfunctional Imidazolium Aryloxide Betaine/Lewis Acid Catalysts as Tools for the Asymmetric Synthesis of Disfavored Diastereomers
Enzymes are Nature's polyfunctional catalysts tailor-made for specific biochemical synthetic transformations, which often proceed with almost perfect stereocontrol. From a synthetic point of view, artificial catalysts usually offer the advantage of much broader substrate scopes, but stereocontrol is often inferior to that possible with natural enzymes. A particularly difficult synthetic task in asymmetric catalysis is to overwrite a pronounced preference for the formation of an inherently favored diastereomer; this requires a high level of stereocontrol. In this Article, the development of a novel artificial polyfunctional catalyst type is described, in which an imidazolium-aryloxide betaine moiety cooperates with a Lewis acidic metal center (here Cu(II)) within a chiral catalyst framework. This strategy permits for the first time a general, highly enantioselective access to the otherwise rare diastereomer in the direct 1,4-addition of various 1,3-dicarbonyl substrates to β-substituted nitroolefins. The unique stereocontrol by the polyfunctional catalyst system is also demonstrated with the highly stereoselective formation of a third contiguous stereocenter making use of a diastereoselective nitronate protonation employing α,β-disubstituted nitroolefin substrates. Asymmetric 1,4-additions of β-ketoesters to α,β-disubstituted nitroolefins have never been reported before in literature. Combined mechanistic investigations including detailed spectroscopic and density functional theory (DFT) studies suggest that the aryloxide acts as a base to form a Cu(II)-bound enolate, whereas the nitroolefin is activated by H-bonds to the imidazolium unit and the phenolic OH generated during the proton transfer. Detailed kinetic analyses (RPKA, VTNA) suggest that (a) the catalyst is stable during the catalytic reaction, (b) not inhibited by product and (c) the rate-limiting step is most likely the C-C bond formation in agreement with the DFT calculations of the catalytic cycle. The robust catalyst is readily synthesized and recyclable and could also be applied to a cascade cyclization.
Willig, Felix,Lang, Johannes,Hans, Andreas C.,Ringenberg, Mark R.,Pfeffer, Daniel,Frey, Wolfgang,Peters, René
supporting information
p. 12029 - 12043
(2019/08/16)

Correction to: Polyfunctional Imidazolium Aryloxide Betaine/Lewis Acid Catalysts as Tools for the Asymmetric Synthesis of Disfavored Diastereomers (Journal of the American Chemical Society (2019) 141 (12029-12043) DOI: 10.1021/jacs.9b04902)
Page 12035 and Supporting Information pp S91-S94. It has come to our attention that the wrong initial concentration of 1a was erroneously used in two experiments of the "same excess" protocol.1 The experiments were thus repeated (0.055 rather than 0.06 mol/L of 1a was erroneously used before), and an excellent overlay of the "time-adjusted same excess" reaction profiles and the standard reaction profile, as previously presented, was found. This indicates that no significant catalyst deactivation takes place and that the active catalyst concentration remains constant during the catalytic reaction. The conclusions are thus not affected by the unintentional error. The corrected Figure 1 is shown below, and a corrected including Figures S1-S28 and Tables S1-S8 (corrected).(Figure Persented).Supporting Information file is available, in which pp S91?S94 have been replaced, in which the correct kinetic experiments are described, including raw data. We apologize for any inconvenience.
Willig, Felix,Lang, Johannes,Hans, Andreas C.,Ringenberg, Mark R.,Pfeffer, Daniel,Frey, Wolfgang,Peters, René
supporting information
p. 17022 - 17022
(2019/11/14)

Dihydro quinazolinone derivative, as well as preparation method and application thereof
The invention relates to the technical field of medicines, in particular to a new dihydro quinazolinone derivative with the following chemical structure general formula and pharmaceutically acceptablesalts thereof, (the formula is shown in the description.), A pharmacological experiment shows that the derivative or the salt provided by the invention has higher inhibitory activity on KRAS-PDE delta protein interaction, and has higher anti-tumor activity in vitro. The invention also provides a preparation method of the derivative and the pharmaceutically acceptable salts thereof, and application to preparatioin of a KRAS-PDE delta inhibitor and an anti-tumor drug.
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Paragraph 0126; 0134; 0135

(2018/07/30)

Discovery of Novel KRAS-PDEδ Inhibitors by Fragment-Based Drug Design
Targeting KRAS-PDEδ protein-protein interactions with small molecules represents a promising opportunity for developing novel antitumor agents. However, current KRAS-PDEδ inhibitors are limited by poor cellular antitumor potency and the druggability of the target remains to be validated by new inhibitors. To tackle these challenges, herein, novel, highly potent KRAS-PDEδ inhibitors were identified by fragment-based drug design, providing promising lead compounds or chemical probes for investigating the biological functions and druggability of KRAS-PDEδ interaction.
Chen, Long,Zhuang, Chunlin,Lu, Junjie,Jiang, Yan,Sheng, Chunquan
supporting information
p. 2604 - 2610
(2018/03/26)

Synthesis of polysiloxane-based quaternized imidazolium salts with a hydroxy group at the end of alkyl groups
A series of polysiloxane derivatives having quaternized imidazolium moieties with hydroxyalkyl groups ([HPImnOH]Xs) (where n is the number of methylene group and X is counter anion) were prepared by quaternization of poly(3-chloropropylmethylsiloxane) (P1) using 1-(ω-hydroxyalkyl)imidazole derivatives (ImnOHs) and anion-exchange reaction using lithium bis(trifluoromethanesulfonyl)imide. Polysiloxane-based quaternized imidazolium salts having hydroxyalkyl groups with chloride anion ([HPImnOH]Cls) were obtained with high quaternization ratio of approximately 100 mol%. The glass transition temperatures (Tgs) of [HPImnOH]Xs were reduced by introducing a hydroxy group at the end of alkyl groups; however, no significant reduction in Tgs was observed by anion exchange from chloride anion to bis(trifluoromethanesulfonyl)imide one (Tf2N-).
Ichikawa, Tsukasa,Wako, Tsuyoshi,Nemoto, Nobukatsu
p. 1 - 8
(2015/12/18)

N-terminal strategy (N1-N4) toward high performance liquid crystal materials
Liquid crystal materials have a variety of applications in many fields such as display techniques as well as photonics and optics. However, only few design principles have been disclosed on liquid crystal materials with different N-heterocycles as the terminal groups, which hinder the development of the heterocyclic liquid crystals. Here, a strategy of molecular design for N-heterocyclic liquid crystal materials is reported. On the basis of this strategy, a series of convenient N-heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,3,4-tetrazole were applied to synthesize the novel liquid crystals. Most of them have proved to exhibit good mesomorphic behaviors which make them excellent components in the mixture of the LCDs materials. The simple attachment of N-heterocyclic units to the liquid crystal molecules through a mild reaction condition will provide a good prospect for the design of N-heterocyclic liquid crystals.
Hong, Fengying,Xia, Zhengce,Zhu, Dezhao,Wu, Hongxiang,Liu, Jianhui,Zeng, Zhuo
supporting information
p. 1285 - 1292
(2017/02/15)

Inhibition of lactoperoxidase-catalyzed oxidation by imidazole-based thiones and selones: A mechanistic study
Herein, we describe the synthesis and biomimetic activity of a series of N,N-disubstituted thiones and selones that contain an imidazole pharmacophore. The N,N-disubstituted thiones do not show any inhibitory activity towards LPO-catalyzed oxidation reactions, but their corresponding N,N-disubstituted selones exhibit inhibitory activity towards LPO-catalyzed oxidation reactions. Substituents on the N atom of the imidazole ring appear to have a significant effect on the inhibition of LPO-catalyzed oxidation and iodination reactions. Selones 16, 17, and 19, which contain methyl, ethyl, and benzyl substituents, exhibit similar inhibition activities towards LPO-catalyzed oxidation reactions with IC50 values of 24.4, 22.5, and 22.5 μM, respectively. However, their activities are almost three-fold lower than that of the commonly used anti-thyroid drug methimazole (MMI). In contrast, selone 21, which contains a N-CH2CH2OH substituent, exhibits high inhibitory activity, with an IC50 value of 7.2 μM, which is similar to that of MMI. The inhibitory activity of these selones towards LPO-catalyzed oxidation/iodination reactions is due to their ability to decrease the concentrations of the co-substrates (H2O2 and I 2), either by catalytically reducing H2O2 (anti-oxidant activity) or by forming stable charge-transfer complexes with oxidized iodide species. The inhibition of LPO-catalyzed oxidation/iodination reactions by N,N-disubstituted selones can be reversed by increasing the concentration of H2O2. Interestingly, all of the N,N-disubstituted selones exhibit high anti-oxidant activities and their glutathione peroxidase (GPx)-like activity is 4-12-fold higher than that of the well-known GPx-mimic ebselen. These experimental and theoretical studies suggest that the selones exist as zwitterions, in which the imidazole ring contains a positive charge and the selenium atom carries a large negative charge. Therefore, the selenium moieties of these selones possess highly nucleophilic character. The 77Se NMR chemical shifts for the selones show large upfield shift, thus confirming the zwitterionic structure in solution. Stop, in the name of love: The inhibition of lactoperoxidase (LPO)-catalyzed reactions by a series of N,N-disubstituted thiones and selones that contain an imidazole pharmacophore is described. The inhibitory activity not only depends on the substituent that is attached to the nitrogen atom, but also on the nature of the chalcogen atom. The inhibition of LPO activity by selones is due to their ability to scavenge the substrate, hydrogen peroxide. Copyright
Roy, Gouriprasanna,Jayaram,Mugesh, Govindasamy
p. 1910 - 1921
(2013/09/02)

Design, synthesis and anti-itch activity evaluation of aromatic amino acid derivatives as gastrin-releasing peptide receptor antagonists
Eight aromatic amino acid derivatives (9a-9h) as gastrin-releasing peptide receptor (GRPR) antagonists were designed and synthesized. For the design, the tertiary structure of GRPR was predicted by blast searching in the premise of 1u19 protein as the template. Eight target compounds were docked into the binding pocket to investigate their possible binding interactions. Their anti-itch activities were tested by intrathecal injection using Kunming mice as experimental animals and chloroquine phosphate as a modeling medium. Compounds 9e and 9f significantly inhibited scratching behaviors. The anti-itch activities of these compounds decreased with the following sequence: 9e > 9f = 9d > 9b > 9g > 9a > 9h > 9c predicted by computer-aided drug design (CADD) and 9e > 9f > 9b > 9h > 9g > 9d > 9a > 9c evaluated by preliminary test. They were broadly in line with activity order pretested by CADD. It showed that the predicted tertiary structure of GRPR could be used for antipruritic drug design.
Yao, Ri-Sheng,Li, Ting-Ting,Xu, Jun,Jiang, Lai-En,Ruan, Ban-Feng
p. 865 - 873
(2012/10/29)

Efficient and selective hydrosilylation of carbonyl compounds catalyzed by iron acetate and N-hydroxyethylimidazolium salts
Aromatic aldehydes, along with aryl alkyl, heteroaryl alkyl, and dialkyl ketones were efficiently reduced to their corresponding primary and secondary alcohols, respectively, in high yields, using the commercially available and inexpensive polymeric silane, polymethylhydrosiloxane (PMHS), as reducing agent. The reaction is catalyzed by in situ generated iron complexes containing hydroxyethyl-functionalized NHC ligands. Turnover frequencies up to 600 h-1 were obtained.
Buitrago, Elina,Tinnis, Fredrik,Adolfsson, Hans
supporting information; experimental part
p. 217 - 222
(2012/03/27)

Group 4 complexes bearing alkoxide functionalized N-heterocyclic carbene ligands as catalysts in the polymerization of olefins
Novel octahedral zirconium complexes bearing alkoxide functionalized N-heterocyclic carbene ligands have been synthesized and characterized. NMR analysis showed that more than one species was obtained during synthesis. The synthesized complexes were able to polymerize ethylene and propylene giving rise to a linear polyethylene with high Mw and polydispersity index often bimodal with molecular weight distribution (MDI) > 2, and highly isotactic polypropylene together with an atactic fraction. Density functional theory (DFT) studies on the complex stability indicate the possible species active during the polymerization reaction.
Costabile, Chiara,Bocchino, Carmen,Napoli, Mariagrazia,Longo, Pasquale
experimental part
p. 3728 - 3735
(2012/10/18)

MUSCARINIC RECEPTOR ANTAGONISTS
The present invention generally relates to muscarinic receptor antagonists of formula I, which are useful, among other uses, for the treatment of various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to the process for the preparation of disclosed compounds, pharmaceutical compositions containing the disclosed compounds, and the methods for treating diseases mediated through muscarinic receptors. Formula (I) wherein Het: is heterocyclyl or heteroaryl X: O, S or NR1 and the other substituents are defined as in the claims.
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Page/Page column 8

(2010/06/19)

METHOD FOR PREPARATION OF REGENERATIVE IMIDAZOLIUM REAGENTS
The present invention relates to novel imidazolium compounds and improved method for the preparation of imidazolium salts. More specifically the invention describes preparation of 1,3-substituted imidazolium reagents whereby the reactive species can be regenerated upon consumption and readily re-usable for versatile chemical transformations. The syntheses of novel imidazolium salts are for applications as oxidizing agent in environmentally electrochemical reactions, internal electrolyte for durable reference electrode and lipophilic salts for anion chemical sensors.
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Page/Page column 6-7

(2010/04/25)

Synthesis and antitubercular screening of imidazole derivatives
A series of imidazole based compounds were synthesized by reacting simple imidazoles with alkyl halides or alkyl halocarboxylate in presence of tetrabutylammonium bromide (TBAB). The compounds bearing carbethoxy group undergo amidation with different amines in the presence of DBU to give respective carboxamides. The synthesized compounds were screened against Mycobacterium tuberculosis where compound 17 exhibited very good in vitro antitubercular activity and may serve as a lead for further optimization.
Pandey, Jyoti,Tiwari, Vinod K.,Verma, Shyam S.,Chaturvedi, Vinita,Bhatnagar,Sinha,Gaikwad,Tripathi, Rama P.
experimental part
p. 3350 - 3355
(2009/12/01)

Synthesis of azolylethyl benzhydryl ethers, analogs of diphenhydramine
Alternative approaches to the preparation of azolylethyl benzhydryl ethers have been studied. It was shown that the reaction of diphenylmethyl halide with 2-(azol-1-yl)ethanol in the presence of triethylamine is the optimum way. An efficient method for the synthesis of 2-(imidazol-1-yl)ethanol using phase-transfer catalysis has been developed.
Burdeinyi,Popkov,Kharchevnikova
experimental part
p. 936 - 939
(2010/10/03)

QUINAZOLINE DERIVATIVES
The invention relates to the use of compounds of the formula I: wherein: ring C is a 5-6 membered heterocyclic moiety; Z is -O-, -S-, or -CH2-; R1 is hydrogen, C1-4alkyl, C1-4alkoxymethyl, di(C1-4)alkoxy)methyl, C1-4alkanoyl, trifluoromethyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, carboxy, C3-7cycloalkyl, C3-7-cycloalkylC1-3alkyl, or an optionally substituted group selected from phenyl, benzyl, phenylC2-4alkyl and a 5-6 membered heterocyclic group; n is an integer from 0 to 5; m is an integer from 0 to 3; R2 represents hydrogen, hydroxy, halgeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NR3R4 (wherein R3 and R4, which may be the same or different, each represents hydrogen or C1-3alkyl), or R5X1- (wherein X1 represents a direct bond, -CH2-, or a heteroatom linker group and R5 is an alkyl, alkenyl or alkynyl chain optionally substituted by for example hydroxy, amino, nitro, alkyl, cycloalkyl, alkoxyalkyl, or an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, which alkyl, alkenyl or alkynyl chain may have a heteroatom linker group, or R5 is an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.
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(2010/02/11)

MANUFACTURING METHOD OF 1-SUBSTITUTED IMIDAZOLE COMPOUND
PROBLEM TO BE SOLVED: To provide a high-yield manufacturing method of a 1-substituted imidazole compound which is expected to be useful as a curing agent for epoxy resins, polyurethane resins or the like, as an intermediate of various agrochemicals, antibiotics or pharmaceuticals such as anti-AIDS agents or the like, or as dye intermediates. SOLUTION: An aldehyde compound is reacted with a primary amine to give an imine compound, and subsequently an α,β-dicarbonyl compound and ammonia are added and allowed to react with the imine compound. Preferably, the α,β-dicarbonyl compound and ammonia are simultaneously added.
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Page 4

(2010/02/11)

Process for manufacture of imidazoles
Imidazoles may be manufactured by reacting a glyoxal, ammonia, an aldehyde, and optionally a primary amine, in the presence of a Bronsted acid whose pKa is approximately equal to the pKa of the ammonium cation of the primary amine, or if the primary amine is not present, to the pKa of the ammonium (NH4+) cation. The reaction may be used to make in relatively high yields a wide variety of imidazoles using relatively inexpensive starting materials. The imidazoles are useful as chemical intermediates.
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(2008/06/13)

Oxindolylquinazoline derivatives as angiogenesis inhibitors
The invention relates to compounds of formula (I) and salts thereof as further defined herein, wherein ring Z is a 6-membered heterocyclic ring containing 1 to 3 nitrogen atoms, and the use of such compounds and salts to inhibit the effects of VEGF and FGF, and in the treatment of a number of disease states including cancer and rheumatoid arthritis.
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(2008/06/13)

Grafted ionic liquid-phase-supported synthesis of small organic molecules
The preparation and applications in the Knoevenagel and 1,3-dipolar cycloaddition reactions of new grafted soluble liquid phases derived from imidazolium ionic liquids are described. Good yields and high regioselectivity are the features observed with these unconventional liquid phases.
Fraga-Dubreuil, Joan,Bazureau, Jean Pierre
p. 6097 - 6100
(2007/10/03)

Cyclosporin compounds, their preparation and the pharmaceutical compositions which contain them
A cyclosporin compound of the formula (I): STR1 wherein Alk and R are as defined herein, or a pharmaceutically acceptable salt thereof, which derivatives are is useful in the treatment and/or prophylaxis of retrovirus infections.
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(2008/06/13)

Synthesis of ω-carbamoyloxyalkylimidazolium salts for evaluation as protective agents against acetylcholinesterase intoxication by soman
A series of N-methyl and N,N-dimethylcarbamoyloxyalkylimidazolium salts has been prepared. The carbamoyloxyalkyl groups are varied from methyl through propyl at the 1,2 or 4 positions of the imidazolium ring. The 2- and 4-substituted series show modest activity as inhibitors of acetylcholinesterase. Several of the compounds show prophylactic activity against soman toxicity but there is no correlation between AChE inhibitory activity and the prophylatic effect, suggesting that reversible carbamoylation is not the basis for the prophylactic effect.
Sundberg, Richard J.,Van Nguyen, Phuoc
p. 123 - 136
(2007/10/03)

Aminodiol HIV protease inhibitors. Synthesis and structure - Activity relationships of P1/P1′ compounds: Correlation between lipophilicity and cytotoxicity
A series of novel aminodiol inhibitors of HIV protease based on the lead compound 1 with structural modifications at P1′ were synthesized in order to reduce the cytotoxicity of 1. We have observed a high degree of correlation between the lipophilicity and the cytotoxicity of this series of inhibitors. It was found that appropriate substitution at the para position of the P1′ phenyl group of 1 resulted in the identification of equipotent (both against the enzyme and in cell culture) compounds (101, 10m, 10n, and 15c) which possess significantly decreased cytotoxicity.
Chen, Ping,Cheng, Peter T. W.,Alam, Masud,Beyer, Barbara D.,Bisacchi, Gregory S.,Dejneka, Tamara,Evans, Adelaide J.,Greytok, Jill A.,Hermsmeier, Mark A.,Humphreys, W. Griffith,Jacobs, Glenn A.,Kocy, Octavian,Lin, Pin-Fang,Lis, Karen A.,Marella, Michael A.,Ryono, Denis E.,Sheaffer, Amy K.,Spergel, Steven H.,Sun, Chong-Qing,Tino, Joseph A.,Vite, Gregory,Colonno, Richard J.,Zahler, Robert,Barrish, Joel C.
p. 1991 - 2007
(2007/10/03)

Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-imidazolyl)alkyl]- 1(2H)-phthalazinones
A number of 4-substituted 2-[ω-(1-imidazolyl)alkyl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane A2 synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.
Yamaguchi,Kamei,Koga,Akima,Kuroki,Ohi
p. 4052 - 4060
(2007/10/02)

TRIAZOLO-1,4-DIAZEPINE DERIVATIVES AND THEIR USE IN PHARMACEUTICALS
A triazolo-1,4-di-azepine compound of the below given formulas and a pharmacologically acceptable salt thereof are disclosed and useful in the pharmaceutical field, especially to allergic diseases. STR1 in which R1 and R2 are hydrogen or an alkyl, R3 is hydrogen or a halogen, R4 is hydrogen or an alkyl, X is--OCO--,--NHCO--,--CO--or others and Y is a cycloalkyl, a cycloalkylalkyl, an alkynyl or others.
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(2008/06/13)