Category: imidazoles-derivatives

《Update on Biotin Therapy in Dermatology: Time for a Change.》 was published in Journal of drugs in dermatology : JDD in 2020. These research results belong to Lipner, Shari R. Synthetic Route of C10H16N2O3S The article mentions the following:

Biotin (vitamin B7 or H) is found in milk, nuts, egg yolks, cereals, supplements, synthesized by intestinal bacteria, and is required for gluconeogenesis, fatty acid synthesis and amino acid catabolism. The results came from multiple reactions, including the reaction of 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5Synthetic Route of 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.Synthetic Route of C10H16N2O3S The biotin/avidin or biotin/streptavidin interaction is utilized in many labeling and purification schemes.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 1973,Journal of General Microbiology included an article by Stutzenberger, F. J.; Parle, J. N.. Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol. The article was titled 《Effect of 2-substituted benzimidazoles on the fungus Pithomyces chartarum》. The information in the text is summarized as follows:

The inhibition of germ-tube elongation in P. chartarum conidia by 2-substituted benzimidazoles varied markedly with the substituted group, 2-(4-thiazolyl)benzimidazole (I) [148-79-8] being the most active. I inhibition of germ-tube elongation was partially eliminated by high concentrations of vitamin B12 [68-19-9], suggesting that I may act as a precursor in the formation of an inactive vitamin B12 coenzyme analog. The inhibition of respiration in germinating spores exposed to I for 3-4 hr appeared to be an indirect effect of I, since I did not affect O uptake or respiratory control of isolated mitochondria. In the experiment, the researchers used 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol)

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Application In Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol 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.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Zeolitic Imidazolate Frameworks for Kinetic Separation of Propane and Propene》 was written by Li, Kunhao; Olson, David H.; Seidel, Jonathan; Emge, Thomas J.; Gong, Hongwei; Zeng, Heping; Li, Jing. Reference of 2-Bromo-1H-imidazoleThis research focused onzinc imidazolate zeolitic framework propane propene separation. The article conveys some information:

Propane/propene separation by cryogenic distillation is one of the most energy and cost intensive industrial processes. Adsorptive separation is a more energy-efficient alternative. Three isostructural zinc imidazolate zeolitic framework materials are found, for the first time, to be promising in the separation of propene and propane based on their different diffusion rates. Fine-tuning of the pore opening size is critical for this type of separation The results came from multiple reactions, including the reaction of 2-Bromo-1H-imidazole(cas: 16681-56-4Reference 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. Reference of 2-Bromo-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Translational Diffusion in a Set of Imidazolium-Based Ionic Liquids [bmim]+A- and Their Mixtures with Water》 was written by Bystrov, Sergei S.; Matveev, Vladimir V.; Egorov, Andrei V.; Chernyshev, Yurii S.; Konovalov, Vladislav A.; Balevicius, Vytautas; Chizhik, Vladimir I.. Safety of 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborateThis research focused ontranslational diffusion imidazolium based ionic liquid water mixture. The article conveys some information:

As the development of the work (J. Phys. Chem. B 2019, 123 (10), 2362-2372) we have investigated the translational mobility in the same set of dried imidazolium-based ionic liquids [bmim]A (A = BF4-, NO3-, TfO-, I-, Br-, and Cl-) in a wide temperature range using NMR technique. It is shown that for the [bmim]+ cation the temperature dependencies of the product Dη do not follow the Stokes-Einstein relation for most systems studied, i.e. there realized so-called “”diffusion-viscosity decoupling””. The correlation between local and translational mobility in pure ionic liquids (IL) of the [bmim][A] type was investigated using the data on NMR relaxation rates and diffusion coefficients The most recent hypothesis of “”water pockets”” in mixtures of IL with water is critically discussed. Considering the totality of data in literature and obtained here, we propose a specific model of the microstructure which may be applied up to water concentrations of 80-90 mol % (the structure of water-rich solutions is out of our current consideration). To confirm the model mol. dynamics simulations of “”IL-water”” mixtures were also carried out. In the experiment, the researchers used many compounds, for example, 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6Safety of 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. Actually, lonic liquids as innovative fluids have received wide attention only during the past two decades. The number of SCI papers published on lonic liquids has exponentially increased from a few in 1996 to >5000 in 2016, exceeding the annual growth rates of other popular scientific areas. Safety of 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Synthesis of bridgehead nitrogen compounds which contain the benzimidazole moiety. 2,3-Dihydro-1H-pyrrolo[1,2-a]benzimidazoles》 was published in Journal of Heterocyclic Chemistry in 1966. These research results belong to Freedman, Allan R.; Payne, Delbert S.; Day, Allan R.. Recommanded Product: 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol The article mentions the following:

An improved synthetic procedure has been developed for the preparation of the title compounds (I). Of the monosubstituted derivatives, only chloro-2,8-dihydro-1H-pyrrolo[1,2-a]benzimidazole was shown to be a mixture of the 6- and 7-isomers. In the part of experimental materials, we found many familiar compounds, such as 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Recommanded Product: 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol)

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) 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. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Recommanded Product: 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Structure-based Design of Pyridone-Aminal eFT508 Targeting Dysregulated Translation by Selective Mitogen-activated Protein Kinase Interacting Kinases 1 and 2 (MNK1/2) Inhibition》 was written by Reich, Siegfried H.; Sprengeler, Paul A.; Chiang, Gary G.; Appleman, James R.; Chen, Joan; Clarine, Jeff; Eam, Boreth; Ernst, Justin T.; Han, Qing; Goel, Vikas K.; Han, Edward Z. R.; Huang, Vera; Hung, Ivy N. J.; Jemison, Adrianna; Jessen, Katti A.; Molter, Jolene; Murphy, Douglas; Neal, Melissa; Parker, Gregory S.; Shaghafi, Michael; Sperry, Samuel; Staunton, Jocelyn; Stumpf, Craig R.; Thompson, Peggy A.; Tran, Chinh; Webber, Stephen E.; Wegerski, Christopher J.; Zheng, Hong; Webster, Kevin R.. Quality Control of Imidazo[1,2-a]pyridine-8-carbonitrile And the article was included in Journal of Medicinal Chemistry on April 26 ,2018. The article conveys some information:

Dysregulated translation of mRNA plays a major role in tumorigenesis. Mitogen-activated protein kinase interacting kinases (MNK)1/2 are key regulators of mRNA translation integrating signals from oncogenic and immune signaling pathways through phosphorylation of eIF4E and other mRNA binding proteins. Modulation of these key effector proteins regulates mRNA, which controls tumor/stromal cell signaling. Compound 23 (eFT508, 6′-((6-aminopyrimidin-4-yl)amino)-8′-methyl-2’H-spiro-[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione hydrochloride), an exquisitely selective, potent dual MNK1/2 inhibitor, was designed to assess the potential for control of oncogene signaling at the level of mRNA translation. The crystal structure-guided design leverages stereoelectronic interactions unique to MNK culminating in a novel pyridone-aminal structure described for the first time in the kinase literature. Compound 23 has potent in vivo antitumor activity in models of diffuse large cell B-cell lymphoma and solid tumors, suggesting that controlling dysregulated translation has real therapeutic potential. Compound 23 is currently being evaluated in Phase 2 clin. trials in solid tumors and lymphoma. Compound 23 is the first highly selective dual MNK inhibitor targeting dysregulated translation being assessed clin. In the experiment, the researchers used many compounds, for example, Imidazo[1,2-a]pyridine-8-carbonitrile(cas: 136117-70-9Quality Control of Imidazo[1,2-a]pyridine-8-carbonitrile)

Imidazo[1,2-a]pyridine-8-carbonitrile(cas: 136117-70-9) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Quality Control of Imidazo[1,2-a]pyridine-8-carbonitrile 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.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《NHC-Catalyzed Oxidative Annulation of α,β-unsaturated Aldehydes with Benzyl Ketones: Direct Access to 4,5,6-Trisubstituted Dihydropyranones》 was written by Wang, Zhan-Yong; Liu, Qingling; Wang, Kai-Kai; Liu, Menghan; Han, Yafei; Sun, Aili; Ma, Xueji. Application of 141556-45-8This research focused ontrisubstituted dihydropyranone preparation green chem; unsaturated aldehyde benzyl ketone oxidative cyclization NHC catalyst. The article conveys some information:

A novel and efficient access to polysubstituted dihydropyranones I (R = Ph, 4-MeOC6H4, 2-furyl, n-Pr, etc.; Ar = Ph, 4-MeC6H4, 4-ClC6H4; Ar1 = Ph, 2-naphthyl, 4-NCC6H4, etc.) was developed by N-heterocyclic carbene catalyzed annulation reaction of α,β-unsaturated aldehydes and benzyl ketones under oxidative conditions. Various α,β-unsaturated aldehydes with long-chain aliphatic and aromatic substitution groups were compatible in this transformation, giving the corresponding products in good to excellent yields under mild conditions. This strategy features simple and readily available materials and mild reaction conditions and provides a green and practical method for the rapid synthesis of functionalized dihydropyranones. In the experiment, the researchers used 1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8Application of 141556-45-8)

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.Application of 141556-45-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 141556-45-8In 2022 ,《Antileishmanial activity and insights into the mechanisms of action of symmetric Au(I) benzyl and aryl-N-heterocyclic carbenes》 was published in Journal of Inorganic Biochemistry. The article was written by Rosa, Leticia B.; Galuppo, Carolina; Lima, Rochanna L. A.; Fontes, Josielle V.; Siqueira, Fabio S.; Judice, Wagner A. S.; Abbehausen, Camilla; Miguel, Danilo C.. The article contains the following contents:

Leishmania amazonensis and L. braziliensis are the main etiol. agents of the American Tegumentary Leishmaniasis (ATL). Taking into account the limited effectiveness and high toxicity of the current drug arsenal to treat ATL, novel options are urgently needed. Inspired by the fact that gold-based compounds are promising candidates for antileishmanial drugs, we studied the biol. action of a systematic series of six (1)-(6) sym. Au(I) benzyl and aryl-N-heterocyclic carbenes. All compounds were active at low micromolar concentrations with 50% effective concentrations ranging from 1.57 to 8.30 μM against Leishmania promastigotes. The mesityl derivative (3) proved to be the best candidate from this series, with a selectivity index ∼13 against both species. The results suggest an effect of the steric and electronic parameters of the N-substituent in the activity. Intracellular infections were drastically reduced after 24h of (2)-(5) incubation in terms of infection rate and amastigote burden. Further investigations showed that our compounds induced significant parasites′ morphol. alterations and membrane permeability. Also, (3) and (6) were able to reduce the residual activity of three Leishmania recombinant cysteine proteases, known as possible targets for Au(I) complexes. Our promising results open the possibility of exploring gold complexes as leishmanicidal mols. to be further screened in in vivo models of infection.1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8Related Products of 141556-45-8) was used in this study.

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.Related Products of 141556-45-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 530-62-1In 2019 ,《Harnessing Secondary Coordination Sphere Interactions That Enable the Selective Amidation of Benzylic C-H Bonds》 was published in Journal of the American Chemical Society. The article was written by Jung, Hoimin; Schrader, Malte; Kim, Dongwook; Baik, Mu-Hyun; Park, Yoonsu; Chang, Sukbok. The article contains the following contents:

Engineering site-selectivity is highly desirable especially in C-H functionalization reactions. We report a new catalyst platform that is highly selective for the amidation of benzylic C-H bonds controlled by π-π interactions in the secondary coordination sphere. Mechanistic understanding of the previously developed iridium catalysts that showed poor regioselectivity gave rise to the recognition that the π-cloud of an aromatic fragment on the substrate can act as a formal directing group through an attractive noncovalent interaction with the bidentate ligand of the catalyst. On the basis of this mechanism-driven strategy, we developed a cationic (η5-C5H5)Ru(II) catalyst with a neutral polypyridyl ligand to obtain record-setting benzylic selectivity in an intramol. C-H lactamization in the presence of tertiary C-H bonds at the same distance. Exptl. and computational techniques were integrated to identify the origin of this unprecedented benzylic selectivity, and robust linear free energy relationship between solvent polarity index and the measured site-selectivity was found to clearly corroborate that the solvophobic effect drives the selectivity. Generality of the reaction scope and applicability toward versatile γ-lactam synthesis were demonstrated.Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Related Products of 530-62-1) was used in this study.

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a coupling agent in the synthesis of dipolar polyamides for nonlinear optical applications and polypeptides. It also used to make β-keto sulfones and sulfoxides, lead sequestering agents, and β-enamino acid derivatives.Related Products of 530-62-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Recommanded Product: 1,3-Dimesityl-1H-imidazol-3-ium chlorideIn 2022 ,《Ruthenium complexes with chelating carboxylate-NHC ligands as efficient catalysts for C-H arylation in water》 was published in Mendeleev Communications. The article was written by Shepelenko, Konstantin E.; Nikolaeva, Ksenia A.; Shevchenko, Maxim A.; Tkachenko, Yurii N.; Minyaev, Mikhail E.; Chernyshev, Victor M.. The article contains the following contents:

Ruthenium(II) complexes [(p-cymene)RuCl(3-R-Im-1-CH2CO2)] (1a-c, H2Im = 2-imidazolylidene; R = Me, Mes, Dipp), [(p-cymene)RuCl(3-R1-Im-1-CH2CONR2)] (2a-d; R1 = Me, Mes, Dipp; R2 = Dipp, tBu, Mes) with chelating N-heterocyclic carbene (NHC) ligands functionalized with carboxy and carboxamidato pendant groups, were prepared and examined as catalysts for ortho-C-H arylation of Ph groups in 2-phenylpyridine and 1-phenylpyrazole with aryl chlorides in water affording substituted 2-(m-terphenylyl)pyridines and 1-(m-terphenylyl)pyrazoles. Complexes with NHC-ligands containing a hemilabile coordinating N-carboxylatomethyl group enable fast and selective ortho-CH-diarylation in the absence of carboxylate-assisting additives. In the experimental materials used by the author, we found 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