Imidazoles-derivatives

A large-scale study of ionic liquids employed in chemistry and energy research to reveal cytotoxicity mechanisms and to develop a safe design guide was written by Dzhemileva, Lilya U.;D’yakonov, Vladimir A.;Seitkalieva, Marina M.;Kulikovskaya, Natalia S.;Egorova, Ksenia S.;Ananikov, Valentine P.. And the article was included in Green Chemistry in 2021.Category: imidazoles-derivatives This article mentions the following:

Device-level applications of organic electrolytes unavoidably imply extensive contact with the environment. Despite their excellent scientific potential, ionic liquids (ILs) cannot be approved for practical usage until their life cycle and impact on the environment are assessed. In this work, we carried out the first large-scale study on the mechanisms of the cytotoxic action of various classes of ionic liquids, including imidazolium, pyridinium, pyrrolidinium, ammonium, and cholinium ILs (25 in total). We determined the biol. effect of these ILs in seven cell lines of various origins (HEK293 (human embryonic kidney), U937 (human myeloid leukemia), Jurkat (human T-cell leukemia), HL60 (human acute promyelocytic leukemia), K562 (human chronic myelogenous leukemia), A549 (human alveolar adenocarcinoma), and A2780 (human ovarian carcinoma)). The induction of apoptosis in cells upon treatment with the majority of the ILs tested was subsequently demonstrated. The new data suggest that ILs trigger the mitochondrial pathway of apoptosis due to the dissipation of the mitochondrial membrane potential and release of cytochrome c from mitochondria into the cytoplasm. The obtained results corroborate the earlier reported data on the cytotoxic effects of ILs, providing new insight into the detailed mechanisms of IL cytotoxicity. In addition, the first illustrative guide to be employed for designing ILs with targeted biol. activity is compiled. As a possible link between the electrochem. behavior of ILs and their biol. activity, the relationship between IL cytotoxicity and the electrophoretic mobility of IL cations is assessed. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Category: imidazoles-derivatives).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Feasibility and physiological relevance of designing highly potent aminopeptidase-sparing leukotriene A4 hydrolase inhibitors was written by Numao, Shin;Hasler, Franziska;Laguerre, Claire;Srinivas, Honnappa;Wack, Nathalie;Jager, Petra;Schmid, Andres;Osmont, Arnaud;Rothlisberger, Patrik;Houguenade, Jeremy;Bergsdorf, Christian;Dawson, Janet;Carte, Nathalie;Hofmann, Andreas;Markert, Christian;Hardaker, Liz;Billich, Andreas;Wolf, Romain M.;Penno, Carlos A.;Bollbuck, Birgit;Miltz, Wolfgang;Rohn, Till A.. And the article was included in Scientific Reports in 2017.SDS of cas: 25676-75-9 This article mentions the following:

Leukotriene A4 Hydrolase (LTA4H) is a bifunctional zinc metalloenzyme that comprises both epoxide hydrolase and aminopeptidase activity, exerted by two overlapping catalytic sites. The epoxide hydrolase function of the enzyme catalyzes the biosynthesis of the pro-inflammatory lipid mediator leukotriene (LT) B4. Recent literature suggests that the aminopeptidase function of LTA4H is responsible for degradation of the tripeptide Pro-Gly-Pro (PGP) for which neutrophil chemotactic activity has been postulated. It has been speculated that the design of epoxide hydrolase selective LTA4H inhibitors that spare the aminopeptidase pocket may therefore lead to more efficacious anti-inflammatory drugs. In this study, we conducted a high throughput screen (HTS) for LTA4H inhibitors and attempted to rationally design compounds that would spare the PGP degrading function. While we were able to identify compounds with preference for the epoxide hydrolase function, absolute selectivity was not achievable for highly potent compounds In order to assess the relevance of designing such aminopeptidase-sparing LTA4H inhibitors, we studied the role of PGP in inducing inflammation in different settings in wild type and LTA4H deficient (LTA4H KO) animals but could not confirm its chemotactic potential. Attempting to design highly potent epoxide hydrolase selective LTA4H inhibitors, therefore seems to be neither feasible nor relevant. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9SDS of cas: 25676-75-9).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.SDS of cas: 25676-75-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electron transfer induced decomposition in potassium-nitroimidazoles collisions: an experimental and theoretical work was written by Mendes, Monica;Garcia, Gustavo;Bacchus-Montabonel, Marie-Christine;Limao-Vieira, Paulo. And the article was included in International Journal of Molecular Sciences in 2019.Synthetic Route of C4H5N3O2 This article mentions the following:

Electron transfer induced decomposition mechanism of nitroimidazole and a selection of analog mols. in collisions with neutral potassium (K) atoms from 10 to 1000 eV have been thoroughly investigated. In this laboratory collision regime, the formation of neg. ions was time-of-flight mass analyzed and the fragmentation patterns and branching ratios have been obtained. The most abundant anions have been assigned to the parent mol. and the nitrogen oxide anion (NO₂^–) and the electron transfer mechanisms are comprehensively discussed. This work focuses on the anal. of all fragment anions produced and it is complementary of our recent work on selective hydrogen loss from the transient neg. ions produced in these collisions. Ab initio theor. calculations were performed for 4-nitroimidazole (4NI), 2-nitroimidazole (2NI), 1-methyl-4- (Me4NI) and 1-methyl-5-nitroimidazole (Me5NI), and imidazole (IMI) in the presence of a potassium atom and provided a strong basis for the assignment of the lowest unoccupied MOs accessed in the collision process. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Synthetic Route of C4H5N3O2).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Synthetic Route of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of imidazo[1,2-a]benzimidazole and imidazolino-[1,2-a]benzimidazole derivatives was written by Simonov, A. M.;Kochergin, P. M.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1965.Application In Synthesis of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole This article mentions the following:

Reaction of 1-alkyl-2-aminobenzimidazoles with α-halo ketones and α-halo alcs. gave the corresponding 1,3-disubstituted 2-iminobenzimidazolines, which under the action of dehydrating agents or by heating with mineral or organic acids lost H₂O and gave derivatives of [1,2-a]benzimidazole (I) or the corresponding 2,3-dihydro compounds Thus were obtained: 1-ethyl-3-phenacyl-2-iminobenzimidazoline, m. 120.5° (aqueous MeOH) [hydrobromide m. 2222.5° (decomposition, MeOH)]; 2-phenyl-9-ethylimidazo[1,2-a]benzimidazole, m. 93-3.5° (aqueous EtOH) [picrate m. 238-40° (decomposition, EtOH)]; 1-ethyl-3-(β-hydroxyethyl)-2-iminobenzimidazoline, m. 122.5-23° (C₂H₄Cl₂) [hydrobromide m. 226.5-27° (decomposition, EtOH); picrate m. 182-3° (H₂O)]; and 9-ethylimidazolino[1,2-a]benzimidazole [picrate m. 267-8° (decomposition, AcOH)]. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Application In Synthesis of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole).

2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Application In Synthesis of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Asymmetric synthesis of cyclic β-amino carbonyl derivatives by a formal [3+2] photocycloaddition was written by Mollari, Leonardo;Valle-Amores, Miguel A.;Martinez-Gualda, Ana M.;Marzo, Leyre;Fraile, Alberto;Aleman, Jose. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Formula: C6H8N2O This article mentions the following:

A visible-light mediated strategy unlocking a family of cyclic β-amino carbonyl derivatives I (R = Me, cyclohexyl, 4-bromophenyl, etc.; R¹ = Ph, naphthalen-2-yl, 4-chlorophenyl, etc.; R² = H, Ts) bearing three contiguous stereogenic centers was introduced. The overall reactivity relies on the performance of the substrate-catalyst complex to assist both the enantiocontrol and the photoredox tasks. This transformation led to an enantioselective [3+2] photocycloaddition between coordinated α,β-unsaturated acyl imidazoles II and cyclopropylamine derivatives III. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Formula: C6H8N2O).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Formula: C6H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Evaluation of gender difference in pharmacokinetics of Candesartan cilexetil in the fasted state by RP-HPLC: A single dose comparative study was written by Nawaz, Hafiz Awais;Masood, Muhammad Irfan;Abbas, Matecn;Usman, Muhammad;Abdul, Muqeet Khan;Rasheed, Huma;Riffat, Sualeha. And the article was included in Pakistan Journal of Pharmaceutical Sciences in 2019.Application In Synthesis of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate This article mentions the following:

To compare the pharmacokinetics of candesartan cilexetil in healthy male and female volunteers in order to identify possible influence of gender and to improve therapeutic outcomes, an HPLC method for the quantification of candesartan cilexetil was developed and validated. Total of 16 volunteers (8 male and 8 female) were registered. Candesartan cilexetil 16 mg was administered orally to all the volunteers and blood samples were collected at different time intervals between 0-72 h. Plasma was separated and analyzed by HPLC method. Pharmacokinetic parameters were calculated by using APO software MW/PHARM version 3.02 and compared in male and female volunteers. The developed HPLC method fulfils the criteria for linearity, accuracy and precision described in EMA guideline. The values for absorption rate constant (Ka), maximum plasma concentration (Cmax), volume of distribution (Vd) and Clearance (CL) were similar in male and female volunteers. No influence of gender was observed on overall pharmaco kinetics of candesartan cilexetil. Therefore, no need for dose optimization while administering candesartan cilexetil in male and female patients was found based on the results of this study. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Application In Synthesis of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Application In Synthesis of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Iron-catalysed alkene and heteroarene H/D exchange by reversible protonation of iron-hydride intermediates was written by Britton, Luke;Docherty, Jamie H.;Sklyaruk, Jan;Cooney, Jessica;Nichol, Gary S.;Dominey, Andrew P.;Thomas, Stephen P.. And the article was included in Chemical Science in 2022.Quality Control of 1-Methylbenzimidazole This article mentions the following:

The iron-catalyzed C(sp²)-H bond hydrogen/deuterium exchange reaction using CD₃OD is reported for both heterocycles (furan, Imidazole, Benzofuran, etc.) and, for the first time, alkenes (4-tert-Butylstyrene, Undecene, Sclareol, etc.). Isolation and characterization, including by single-crystal X-ray diffraction, of the key iron-aryl and iron-alkenyl C-H metalation intermediates provided evidence for a reversible protonation of the active iron hydride catalyst. Good chemoselectivity was observed for both substrate classes. The developed procedure is orthogonal to previous iron-catalyzed H/D exchange methods which used C₆D₆, D₂, or D₂O as the deuterium source, and uses only bench-stable reagents, including the iron(II) pre-catalyst. Further, a new mechanism of iron-hydride formation is reported in which β-hydride elimination from an alc. generates the iron hydride. The ability to produce, isolate and characterize the organometallic products arising from C-H activation presents a basis for future discovery and development. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Quality Control of 1-Methylbenzimidazole).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Quality Control of 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Binary mixtures of homologous room-temperature ionic liquids: Temperature and composition evolution of the nanoscale structure was written by Pontoni, Diego;DiMichiel, Marco;Deutsch, Moshe. And the article was included in Journal of Molecular Liquids in 2021.Safety of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

Using X-ray scattering from binary mixtures of [C_nmim][NTf₂] room temperature ionic liquids (RTILs) with n = 8,12 we study their nanoscale layering and its evolution with temperature T and mole fraction x of [C₈mim][NTf₂]. The layers’ lateral structure, dominated by the common headgroups’ Coulomb interaction in the layer’s polar slab, and by the chain-chain van der Waals interaction in the apolar slab, hardly changes. However, the longitudinal layer spacing, dI, decreases with x, exhibiting domination by [C₁₂mim][NTf₂] at least up to x â‰?0.5. The layering order’s range decreases uniformly with x. dI is found to deviate pos. from an ideal mixture spacing by up to â‰?%. The lateral spacings’ deviations are 10-fold smaller, implying the nanoscale excess volume to be also â‰?%, 100-fold larger than those obtained from macroscopic molar d. measurements. This gap is probably bridged at the larger length scales of these RTILs’ hierarchical order. Increasing T decreases the d_I deviations, but only marginally. The pos., and T-decreasing, d_I deviations from ideality contrast strongly with the neg., 100-fold smaller, and T-increasing, deviations found for liquid normal-alkane mixtures of the same lengths, but fully agree with the pos. similar-percent deviations obtained from the modified Vegard’s law for soft-solid rotator phases of binary mixtures of alkanes and of alcs. These results attest against a liquid-like chain packing in the apolar slab of the RTILs, but strongly support an interdigitated, roughly layer normal, chain packing. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Safety of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Safety of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Automatic data analysis workflow for ultra-high performance liquid chromatography-high resolution mass spectrometry-based metabolomics was written by Yu, Yong-Jie;Zheng, Qing-Xia;Zhang, Yue-Ming;Zhang, Qian;Zhang, Yu-Ying;Liu, Ping-Ping;Lu, Peng;Fan, Mei-Juan;Chen, Qian-Si;Bai, Chang-Cai;Fu, Hai-Yan;She, Yuanbin. And the article was included in Journal of Chromatography A in 2019.Application of 145040-37-5 This article mentions the following:

Data anal. for ultra-performance liquid chromatog. high-resolution mass spectrometry-based metabolomics is a challenging task. The present work provides an automatic data anal. workflow (AntDAS2) by developing three novel algorithms, as follows: (i) a d.-based ion clustering algorithm is designed for extracted-ion chromatogram extraction from high-resolution mass spectrometry; (ii) a new maximal value-based peak detection method is proposed with the aid of automatic baseline correction and instrumental noise estimation; and (iii) the strategy that clusters high-resolution m/z peaks to simultaneously align multiple components by a modified dynamic programing is designed to efficiently correct time-shift problem across samples. Standard compounds and complex datasets are used to study the performance of AntDAS2. AntDAS2 is better than several state-of-the-art methods, namely, XCMS Online, Mzmine2, and MS-DIAL, to identify underlying components and improve pattern recognition capability. Meanwhile, AntDAS2 is more efficient than XCMS Online and Mzmine2. A MATLAB GUI of AntDAS2 is designed for convenient anal. and is available at the following webpage: http://software.tobaccodb.org/software/antdas2. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Application of 145040-37-5).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Application of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Photoredox-Catalyzed Decarboxylative C-H Acylation of Heteroarenes was written by Jia, Wei;Jian, Yong;Huang, Binbin;Yang, Chao;Xia, Wujiong. And the article was included in Synlett in 2018.Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly realize the acylation of various heterocyclic compounds In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem