Category: imidazoles-derivatives

In 2018,Barresi, Elisabetta; Giacomelli, Chiara; Daniele, Simona; Tonazzini, Ilaria; Robello, Marco; Salerno, Silvia; Piano, Ilaria; Cosimelli, Barbara; Greco, Giovanni; Da Settimo, Federico; Martini, Claudia; Trincavelli, Maria Letizia; Taliani, Sabrina published 《Novel fluorescent triazinobenzimidazole derivatives as probes for labeling human A1 and A2B adenosine receptor subtypes》.Bioorganic & Medicinal Chemistry published the findings.Quality Control of 2-Chloro-1H-benzo[d]imidazole The information in the text is summarized as follows:

The expression levels and the subcellular localization of adenosine receptors (ARs) are affected in several pathol. conditions as a consequence of changes in adenosine release and metabolism In this respect, labeled probes able to monitor the AR expression could be a useful tool to investigate different pathol. conditions. Herein, novel ligands for ARs, bearing the fluorescent 7-nitrobenzofurazan (NBD) group linked to the N1 (1,2) or N10 (3,4) nitrogen of a triazinobenzimidazole scaffold, were synthesized. The compounds were biol. evaluated as fluorescent probes for labeling A1 and A2B AR subtypes in bone marrow-derived mesenchymal stem cells (BM-MSCs) that express both receptor subtypes. The binding affinity of the synthesized compounds towards the different AR subtypes was determined The probe 3 revealed a higher affinity to A1 and A2B ARs, showing interesting spectroscopic properties, and it was selected as the most suitable candidate to label both AR subtypes in undifferentiated MSCs. Fluorescence confocal microscopy showed that compound 3 significantly labeled ARs on cell membranes and the fluorescence signal was decreased by the cell pre-incubation with the A1 AR and A2B AR selective agonists, R-PIA and BAY 60-6583, resp., thus confirming the specificity of the obtained signal. In conclusion, compound 3 could represent a useful tool to investigate the expression pattern of both A1 and A2B ARs in different pathol. and physiol. processes. Furthermore, these results provide an important basis for the design of new and more selective derivatives able to monitor the expression and localization of each different ARs in several tissues and living cells. In addition to this study using 2-Chloro-1H-benzo[d]imidazole, there are many other studies that have used 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Quality Control of 2-Chloro-1H-benzo[d]imidazole) was used in this study.

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.Quality Control of 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2015,Kancharla, Papireddy; Kelly, Jane Xu; Reynolds, Kevin A. published 《Synthesis and Structure-Activity Relationships of Tambjamines and B-Ring Functionalized Prodiginines as Potent Antimalarials》.Journal of Medicinal Chemistry published the findings.Quality Control of 2-Bromo-1H-imidazole The information in the text is summarized as follows:

Synthesis and antimalarial activity of 94 novel bipyrrole tambjamines (TAs) and a library of B-ring functionalized tripyrrole prodiginines (PGs) against a panel of Plasmodium falciparum strains are described. The activity and structure-activity relationships demonstrate that the ring-C of PGs can be replaced by an alkylamine, providing for TAs with retained/enhanced potency. Furthermore, ring-B of PGs/TAs can be substituted with short alkyl substitutions at either 4-position (replacement of OMe) or 3- and 4-positions without impacting potency. Eight representative TAs and two PGs have been evaluated for antimalarial activity against multidrug-resistant P. yoelii in mice in the dose range of 5-100 mg/kg × 4 days by oral administration. The KAR425 TA (I) offered greater efficacy than previously observed for any PG, providing 100% protection to malaria-infected mice until day 28 at doses of 25 and 50 mg/kg × 4 days, and was also curative in this model in a single oral dose (80 mg/kg). This study presents the first account of antimalarial activity in tambjamines. In the part of experimental materials, we found many familiar compounds, such as 2-Bromo-1H-imidazole(cas: 16681-56-4Quality Control of 2-Bromo-1H-imidazole)

2-Bromo-1H-imidazole(cas: 16681-56-4) is a member of imidazole. Its exclusive structural characteristics with enviable electron-rich features are favorable for imidazole-based fused heterocycles to bind efficiently with an array of enzymes and receptors in biological systems through various weak interactions like hydrogen bonds, ion-dipole, cation-π, π-π stacking, coordination, Van der Waals forces, hydrophobic effects, etc., and therefore they demonstrate widespread bioactivities. Quality Control of 2-Bromo-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Category: imidazoles-derivativesOn September 30, 1981 ,《The reaction of imidazolidine-2-thione with carbon disulfide》 was published in Journal of the Chemical Society. The article was written by Yokoyama, Masataka; Motozawa, Kosei; Kawamura, Eiichi; Imamoto, Tsuneo. The article contains the following contents:

The reaction of imidazolidine-2-thione (I) with CS2 in the presence of strong bases is reported. E. g., in the presence of NaH (THF/HMPA/DMSO) 64% bis(thioamide) II and 16% tetrahydrodiimidazothiadiazinethione III were formed, whereas reaction of I with CS2 using BuLi, followed by methylation gave 79% carbodithiolate IV. In the experiment, the researchers used many compounds, for example, Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2Category: imidazoles-derivatives)

Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. Category: imidazoles-derivatives In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Venable, Jennifer D.; Cai, Hui; Chai, Wenying; Dvorak, Curt A.; Grice, Cheryl A.; Jablonowski, Jill A.; Shah, Chandra R.; Kwok, Annette K.; Ly, Kiev S.; Pio, Barbara; Wei, Jianmei; Desai, Pragnya J.; Jiang, Wen; Nguyen, Steven; Ling, Ping; Wilson, Sandy J.; Dunford, Paul J.; Thurmond, Robin L.; Lovenberg, Timothy W.; Karlsson, Lars; Carruthers, Nicholas I.; Edwards, James P. published their research in Journal of Medicinal Chemistry on December 29 ,2005. The article was titled 《Preparation and Biological Evaluation of Indole, Benzimidazole, and Thienopyrrole Piperazine Carboxamides: Potent Human Histamine H4 Antagonists》.Product Details of 3584-66-5 The article contains the following contents:

Three series of H4 receptor ligands, derived from indoly-2-yl-(4-methyl-piperazin-1-yl)methanones, have been synthesized and their structure-activity relationships evaluated for activity at the H4 receptor in competitive binding and functional assays. In all cases, substitution of small lipophilic groups in the 4 and 5-positions led to increased activity in a [3H]histamine radiolabeled ligand competitive binding assay. In vitro metabolism and initial pharmacokinetic studies were performed on selected compounds leading to the identification of carboxamides I [X = CH, N] as potent H4 antagonists with the potential for further development. In addition, I demonstrated efficacy in in vitro mast cell and eosinophil chemotaxis assays. After reading the article, we found that the author used 5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole(cas: 3584-66-5Product Details of 3584-66-5)

5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole(cas: 3584-66-5) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
However, the application of imidazoles is not limited to the field of peptides and peptidomimetics. Product Details of 3584-66-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

COA of Formula: C10H16N2O3SIn 2019 ,《Artificial Metalloenzymes Based on the Biotin-Streptavidin Technology: Enzymatic Cascades and Directed Evolution》 appeared in Accounts of Chemical Research. The author of the article were Liang, Alexandria Deliz; Serrano-Plana, Joan; Peterson, Ryan L.; Ward, Thomas R.. The article conveys some information:

A review. Artificial metalloenzymes (ArMs) result from anchoring a metal-containing moiety within a macromol. scaffold (protein or oligonucleotide). The resulting hybrid catalyst combines attractive features of both homogeneous catalysts and enzymes. This strategy includes the possibility of optimizing the reaction by both chem. (catalyst design) and genetic means leading to achievement of a novel degree of (enantio)selectivity, broadening of the substrate scope, or increased activity, among others. In the past 20 years, the Ward group has exploited, among others, the biotin-(strept)avidin technol. to localize a catalytic moiety within a well-defined protein environment. Streptavidin has proven versatile for the implementation of ArMs as it offers the following features: (i) it is an extremely robust protein scaffold, amenable to extensive genetic manipulation and mishandling, (ii) it can be expressed in E. coli to very high titers (up to >8 g·L-1 in fed-batch cultures), and (iii) the cavity surrounding the biotinylated cofactor is commensurate with the size of a typical metal-catalyzed transition state. Relying on a chemogenetic optimization strategy, varying the orientation and the nature of the biotinylated cofactor within genetically engineered streptavidin, 12 reactions have been reported by the Ward group thus far. Recent efforts within our group have focused on extending the ArM technol. to create complex systems for integration into biol. cascade reactions and in vivo. With the long-term goal of complementing in vivo natural enzymes with ArMs, we summarize herein three complementary research lines: (i) With the aim of mimicking complex cross-regulation mechanisms prevalent in metabolism, we have engineered enzyme cascades, including cross-regulated reactions, that rely on ArMs. These efforts highlight the remarkable (bio)compatibility and complementarity of ArMs with natural enzymes. (ii) Addnl., multiple-turnover catalysis in the cytoplasm of aerobic organisms was achieved with ArMs that are compatible with a glutathione-rich environment. This feat is demonstrated in HEK-293T cells that are engineered with a gene switch that is upregulated by an ArM equipped with a cell-penetrating module. With this goal in mind, we have identified E. coli’s periplasmic space and surface display to compartmentalize an ArM, while maintaining the critical phenotype-genotype linkage. (iii) Finally, ArMs offer the fascinating prospect of “”endowing organometallic chem. with a genetic memory.””. This strategy offers a straightforward means to optimize by directed evolution the catalytic performance of ArMs. Five reactions have been optimized following these compartmentalization strategies: ruthenium-catalyzed olefin metathesis, ruthenium-catalyzed deallylation, iridium-catalyzed transfer hydrogenation, dirhodium-catalyzed cyclopropanation and carbene insertion in C-H bonds. Importantly, >100 turnovers were achieved with ArMs in E. coli whole cells, highlighting the multiple turnover catalytic nature of these systems. In the part of experimental materials, we found many familiar compounds, such as 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5COA of Formula: C10H16N2O3S)

5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5) may be used to elute proteins from avidin/streptavidin resins. It has been used for culturing of oligodendrocytes.COA of Formula: C10H16N2O3S And it has been used as a vitamin supplement for the growth of Bacillus species.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Product Details of 16681-56-4In 2006 ,《Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH》 appeared in Organic & Biomolecular Chemistry. The author of the article were Clyne, Mairead A.; Aldabbagh, Fawaz. The article conveys some information:

Six-membered photochem. cyclizations of 2-iodo-N-(2-arylethyl)imidazoles proceeded regioselectively in higher yields than the equivalent tin hydride-mediated reactions. E.g., photochem. cyclizations of 2-iodo-N-(2-arylethyl)imidazole I gave 70% 5,6-dihydroimidazo[2,1-a]isoquinoline II. The decrease in yield of cyclization products, 5,6-dihydroimidazo[2,1-a]isoquinolines containing strongly deactivating substituents on the aryl ring confirmed the electrophilic nature of the σ-imidazol-2-yl radicals. The seven-membered cyclization was only successful under photochem. conditions, as radical reduction occurred with tin hydride. Nitration of 5,6-dihydroimidazo[2,1-a]isoquinolines with nitric/sulfuric acid occurred at the 2- and 8-positions. In the experiment, the researchers used many compounds, for example, 2-Bromo-1H-imidazole(cas: 16681-56-4Product Details of 16681-56-4)

2-Bromo-1H-imidazole(cas: 16681-56-4) is a member of imidazole. Its exclusive structural characteristics with enviable electron-rich features are favorable for imidazole-based fused heterocycles to bind efficiently with an array of enzymes and receptors in biological systems through various weak interactions like hydrogen bonds, ion-dipole, cation-π, π-π stacking, coordination, Van der Waals forces, hydrophobic effects, etc., and therefore they demonstrate widespread bioactivities. Product Details of 16681-56-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Liu, Yaxu; Scattolin, Thomas; Gobbo, Alberto; Belis, Marek; Van Hecke, Kristof; Nolan, Steven P.; Cazin, Catherine S. J. published an article in European Journal of Inorganic Chemistry. The title of the article was 《A Simple Synthetic Route to Well-Defined [Pd(NHC)Cl(1-tBu-indenyl)] Pre-catalysts for Cross-Coupling Reactions》.Recommanded Product: 1,3-Dimesityl-1H-imidazol-3-ium chloride The author mentioned the following in the article:

A simple synthetic access to [Pd(NHC)Cl(1-tBu-indenyl)] complexes bearing different saturated and unsaturated NHC ligands was reported. All complexes were obtained in excellent yields under mild conditions (60°C, 1 h) in the presence of the weak base K2CO3 in green acetone as the solvent. We view synthetic access as vital in delineating the precatalyst choice and have demonstrated here the facile access to these complexes was reported. The catalytic activity of the synthesized derivatives were investigated on three different cross-coupling reactions such as Suzuki-Miyaura, unconventional Suzuki-Miyaura reaction and Buchwald-Hartwig amination to form Ar1Ar2 [Ar1 = Ph, 4-MeC6H4, 4-FC6H4, etc.; Ar2 = Ph, 4-MeOC6H4, 4-MeC6H4, etc.], and PhC(O)Ar [Ar = Ph, 3-MeOC6H4, 4-MeC6H4, etc.], R1NR2R3 [R1 = 4-OMe, 4-CF3; R2 = Ph, R3 = Me; R2R3 = CH2CH2OCH2CH2] resp.. Complex [Pd(IPr*)Cl(1-tBu-indenyl)], which borne the less electron-donating IPrCl ligand, showed the best performance on conventional Suzuki-Miyaura reaction of (aryl chlorides/arylboronic acids) and Buchwald-Hartwig amination using MeOH/THF and the green 2-MeTHF as solvents, resp. Moreover, for the challenging unconventional Suzuki-Miyaura reaction between esters and arylboronic acids, [Pd(IPr*)Cl(1-tBu-indenyl)] showed the highest activity among all catalysts tested. In the experiment, the researchers used 1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8Recommanded Product: 1,3-Dimesityl-1H-imidazol-3-ium chloride)

1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8) is a ligand for arylation of aldehydes and for carbene catalyzed intermolecular arylation of C-H bonds. It is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases.Recommanded Product: 1,3-Dimesityl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Dual-Mode Fluorescence and Magnetic Resonance Imaging by Perylene Diimide-Based Gd-Containing Magnetic Ionic Liquids》 was written by Yu, Xiaoliang; Yuan, Xiaoyan; Huang, Zitan; Zhang, Wenyu; Huang, Fan; Ren, Lixia. Application of 616-47-7 And the article was included in ACS Biomaterials Science & Engineering in 2020. The article conveys some information:

Bioimaging plays a key role in the diagnosis/treatment of diseases and in scientific research studies. Compared with single imaging techniques, dual-mode and multimode imaging techniques facilitate high accuracy. In this work, a perylene diimide (PDI)-based Gd-containing magnetic ionic liquid, Per-6-Diimi[Gd(NO3)4], is reported for dual-modal imaging, in which a Gd(III) complex was used for magnetic resonance imaging (MRI), while PDI was used for fluorescence imaging. Because of the difference in the biol. microenvironment, there is a switch between dispersed and aggregated states of Per-6-Diimi[Gd(NO3)4] mols. in hydrophobic and hydrophilic media. When it was in the aqueous solution, the intensive π-π interaction of PDI cores made Per-6-Diimi[Gd(NO3)4] aggregates to form particles. The paramagnetic nanoparticles ensure prolonging the rotational correlation time, which results in a strong enhancement of MRI with a longitude relaxation coefficient of 14.94 mM-1 s-1. In an in vivo MRI experiment, the tumor site is imaged by MRI through the enhanced permeability and retention effect. However, when the mol. is present on the hydrophobic membrane of the cells, the dispersed Per-6-Diimi[Gd(NO3)4] showed good fluorescence imaging capabilities due to the high fluorescence quantum yield of PDI. Thus, the fluorescence imaging of cells can be carried out. Moreover, ex vivo fluorescence imaging of organs is performed after MRI. Per-6-Diimi[Gd(NO3)4] is enriched in the liver, kidneys, and tumors. The results came from multiple reactions, including the reaction of 1-Methyl-1H-imidazole(cas: 616-47-7Application of 616-47-7)

1-Methyl-1H-imidazole(cas: 616-47-7) is actively involved in removing acid during the production of diethoxyphenylphosphine. It is used as an intermediate in organic synthesis.Application of 616-47-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《The effect of nanoscale friction of mesoporous carbon supported ionic liquids on the mass transfer of CO2 adsorption》 was published in Physical Chemistry Chemical Physics in 2020. These research results belong to Fan, Pengpeng; Qiu, Xiuhua; Shah, Faiz Ullah; Ji, Qingmin; An, Rong. SDS of cas: 174501-65-6 The article mentions the following:

Supported ionic liquids (ILs) are attractive alternatives for CO2 capture and the thickness of supported IL films plays a critical role in the CO2 mass transfer rate. However, the dependence of CO2 uptake on the IL film thickness differs as the system varies. In this work, at. force microscopy (AFM) is employed to probe the ‘nanofriction coefficient’ to characterize the mobility of ILs at the solid interface, in which, the smaller the nanofriction coefficient, the faster are the ionic mobility and CO2 mass transfer. A monotonic and almost linear relationship for supported IL films is obtained between the resistance of CO2 mass transfer (1/k) and the nanofriction coefficient (μ), avoiding the controversy over the effect of supported IL film thickness on CO2 adsorption. The enhanced mass transfer of CO2 adsorption at IL-solid interfaces is observed at smaller resistance 1/k and friction coefficient μ. The low-friction driven local mobility (diffusion) of ILs at solid interfaces is enhanced, promoting the exchange mixing of the ILs adsorbing CO2 with the ‘blank-clean’ ions of the ILs, and thus accelerating the CO2 mass transfer. The proposed correlation links the nanoscale friction with the mass transfer of CO2 adsorption, providing a fresh view on the design of ultra-low frictional supported ILs for enhanced CO2 capture and separation processes. In the experimental materials used by the author, we found 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6SDS of cas: 174501-65-6)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. A multidisciplinary study on lonic liquids is emerging, including chemistry, materials science, chemical engineering, and environmental science. More specifically, some important fundamental viewpoints are now different from the original concepts, as insights into the nature of lonic liquids become deeper. For example, the physicochemical properties of lonic liquids are now recognized as ranging broadly from the oft quoted “nonvolatile, non-flammable, and air and water stable” to those that are distinctly volatile, flammable, and unstable. SDS of cas: 174501-65-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Pharmacophore modelling of 2-chlorobenzimidazole and its specific docking to the active site c-Met Kinase: A search for potent c-Met Kinase inhibitor》 was published in Pharmaceutical and Chemical Journal in 2020. These research results belong to Otuokere, I. E.; Igwe, K. K.; Amaku, J. F.; Ikpeazu, O. V.. SDS of cas: 4857-06-1 The article mentions the following:

In this paper, we demonstrate how pharmacophore modeling was used to design the analogs of 2-chlorobenzimidazole and the application of mol. docking studies in the evaluation of the ligand affinity for the target. The lead mol. (1-benzyl-2-chloro-1H-benzimidazole) had the highest docking score of -8.0 kcal/mol and was observed to interact with 17 amino acids within the pocket of c-Met Kinase (ALA159, VAL39, TYR32, MET144, ASN142, ARG141, ALA154, ASP155, ALA49, LYS51, LEU90, TYR92, MET93, GLY32, ILE, ASP97 and GLY96). Meanwhile, the ADME characteristics of 1-benzyl-2-chloro-1H-benzimidazole showed approving properties of the lead mol. Hence, we recommend 1-benzyl-2-chloro-1H-benzimidazoleas promising candidates with high potential to inhibit c-Met Kinase.2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1SDS of cas: 4857-06-1) was used in this study.

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.SDS of cas: 4857-06-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem