Category: imidazoles-derivatives

Photoredox Catalysis for Silyl-Mediated C-H Alkylation of Heterocycles with Non-Activated Alkyl Bromides was written by Perkins, James J.;Schubert, Jeffrey W.;Streckfuss, Eric C.;Balsells, Jaume;ElMarrouni, Abdellatif. And the article was included in European Journal of Organic Chemistry in 2020.Name: 1-Methylbenzimidazole This article mentions the following:

The development of a Minisci reaction of electron-deficient heteroarenes with non-activated alkyl bromides under visible-light photoredox catalysis is disclosed. Optimization of the reaction led to identification of mild, general, and practical reaction conditions compatible with sensitive functional groups. The scope of this transformation allowed late-stage functionalization of pharmaceutical products containing electron-deficient heteroarenes in a parallel fashion. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Name: 1-Methylbenzimidazole).

1-Methylbenzimidazole (cas: 1632-83-3) 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 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.Name: 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Identification of RP-6685, an Orally Bioavailable Compound that Inhibits the DNA Polymerase Activity of Polθ was written by Bubenik, Monica;Mader, Pavel;Mochirian, Philippe;Vallee, Frederic;Clark, Jillian;Truchon, Jean-Francois;Perryman, Alexander L.;Pau, Victor;Kurinov, Igor;Zahn, Karl E.;Leclaire, Marie-Eve;Papp, Robert;Mathieu, Marie-Claude;Hamel, Martine;Duffy, Nicole M.;Godbout, Claude;Casas-Selves, Matias;Falgueyret, Jean-Pierre;Baruah, Prasamit S.;Nicolas, Olivier;Stocco, Rino;Poirier, Hugo;Martino, Giovanni;Fortin, Alexanne Bonneau;Roulston, Anne;Chefson, Amandine;Dorich, Stephane;St-Onge, Miguel;Patel, Purvish;Pellerin, Charles;Ciblat, Stephane;Pinter, Thomas;Barabe, Francis;El Bakkouri, Majida;Parikh, Paranjay;Gervais, Christian;Sfeir, Agnel;Mamane, Yael;Morris, Stephen J.;Black, W. Cameron;Sicheri, Frank;Gallant, Michel. And the article was included in Journal of Medicinal Chemistry in 2022.Reference of 25676-75-9 This article mentions the following:

DNA polymerase theta (Polθ) is an attractive synthetic lethal target for drug discovery, predicted to be efficacious against breast and ovarian cancers harboring BRCA-mutant alleles. Here, we describe our hit-to-lead efforts in search of a selective inhibitor of human Polθ (encoded by POLQ). A high-throughput screening campaign of 350,000 compounds identified an 11 micromolar hit, giving rise to the N2-substituted fused pyrazolo series, which was validated by biophys. methods. Structure-based drug design efforts along with optimization of cellular potency and ADME ultimately led to the identification of RP-6685 (I): a potent, selective, and orally bioavailable Polθ inhibitor that showed in vivo efficacy in an HCT116 BRCA2^-/- mouse tumor xenograft model. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Reference of 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 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.Reference of 25676-75-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Manganese-Catalyzed Asymmetric Hydrogenation of Quinolines Enabled by π-π Interaction** was written by Liu, Chenguang;Wang, Mingyang;Liu, Shihan;Wang, Yujie;Peng, Yong;Lan, Yu;Liu, Qiang. And the article was included in Angewandte Chemie, International Edition in 2021.Reference of 3012-80-4 This article mentions the following:

The non-noble metal-catalyzed asym. hydrogenation of N-heteroaromatics, quinolines, is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the asym. hydrogenation of quinolines, affording high yields and enantioselectivities (up to 97% ee). A turnover number of 3840 was reached at a low catalyst loading (S/C=4000), which is competitive with the activity of most effective noble metal catalysts for this reaction. The precise regulation of the enantioselectivity were ensured by a π-π interaction. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Reference of 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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 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).Reference of 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Oxidative alkylation of azoles: V. Synthesis of 1-chloro-4-nitroimidazole and its reaction with methyl iodide was written by Veretennikov, E. A.;Pevzner, M. S.. And the article was included in Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) in 1997.Recommanded Product: 3034-41-1 This article mentions the following:

Chlorination of 4-nitroimidazole in alk. medium gave 1-chloro-4-nitroimidazole. The reaction of the latter with Me iodide results in liberation of iodine and formation of 4-nitroimidazole, isomeric 1-methyl-4-nitro- and 1-methyl-5-nitroimidazoles, and 1,3-dimethyl-4-nitroimidazolium triiodide. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 3034-41-1).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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.Recommanded Product: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Inhibition of bacterial growth and galactosyltransferase activity of WbwC by α, ω-bis(3-alkyl-1H-imidazolium)alkane salts: Effect of varying carbon content was written by Kocev, Alexander;Melamed, Jacob;Wang, Shuo;Kong, Xianqi;Vlahakis, Jason Z.;Xu, Yaozu;Szarek, Walter A.;Brockhausen, Inka. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Related Products of 21252-69-7 This article mentions the following:

A series of compounds was designed and synthesized having two imidazolium rings separated by a polymethylene spacer and having alkyl substituents on each of the imidazolium rings. The compounds were assayed for their effects on the activity of galactosyltransferase WbwC, and also on the growth of Gram-neg. and Gram-pos. bacteria, as well as human cells. The inhibition observed on enzyme activities and cell growth was dependent on the total number of carbons in the spacer and the alkyl substituents on the imidazolium rings. These readily synthesized, achiral compounds have potential as antimicrobial and antiseptic agents. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Related Products of 21252-69-7).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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. 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).Related Products of 21252-69-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ionization constants, and ultraviolet and infrared spectra of 4(7)- and 5(6)-halogenated benzimidazoles was written by Rabiger, D. J.;Joullie, M. M.. And the article was included in Journal of the Chemical Society in 1964.Reference of 83741-35-9 This article mentions the following:

For a series of 4(7)- and 5(6)-halogenated benzimidazoles, the ionization constants show that for compounds with a halogen atom in either the 4(7)- or the 5(6)-position the basicity decreases in the order F > I > Cl > Br. Attempts were made to correlate the effect of substituents on the pK_a values of benzimidazoles by means of the Hammett equation; no relation could be established for 5(6)-substituted compounds, presumably because of the tautomeric nature of the ring, but a satisfactory correlation was obtained for the 4(7)- halogenated benzimidazoles. The ultraviolet data indicate that the implied order of overall electron release for halogen atoms in both the 4(7)- and the 5(6)-position is I > Br > Cl > F. The infrared spectra of these halogenated benzimidazoles are discussed. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-benzoimidazole (cas: 83741-35-9Reference of 83741-35-9).

4-Bromo-1H-benzoimidazole (cas: 83741-35-9) 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 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).Reference of 83741-35-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Characterization of the ionic liquid obtained by chlorosulfonation of 1-methylimidazole: 1-methyl-3-sulfonic acid imidazolium chloride, 1-methylimidazolium chlorosulfate or a zwitterionic salt? was written by Urban, Bela;Szalontai, Gabor;Papp, Mate;Feher, Csaba;Benyei, Attila C.;Skoda-Foldes, Rita. And the article was included in Journal of Molecular Liquids in 2021.Safety of 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

A great number of organic reactions catalyzed by the ionic liquid product of chlorosulfonation of 1-methylimidazole have been reported recently. At the same time controversial assumptions have appeared on the real structure of the catalyst. In the present report the primarily formed chlorosulfonation product is proved to be 1-methylimidazolium chlorosulfate ([HMim]⁺[SO₃Cl]^–) instead of 1-methyl-3-sulfonic acid imidazolium chloride, reported previously. The former structure is confirmed by X-ray crystallog. and NMR spectroscopy, including ¹H-, ¹³C-, ¹⁷O- and ¹⁵N-¹H HSQC measurements. ¹H and ¹⁷O NMR experiments support fast hydrolysis of [HMim] [SO₃Cl] resulting in the formation of [HMim][HSO₄] in the presence of traces of water. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Safety of 1-Methyl-1H-imidazol-3-ium chloride).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Safety of 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Exploitation of localized surface plasmon resonance of silver/gold nanoparticles for the fluorescence quantification of angiotensin II receptor antagonists in their tablets and bio-samples was written by Alarfaj, N. A.;Altamimi, S. A.;El-Tohamy, M. F.;Almahri, A. M.. And the article was included in New Journal of Chemistry in 2019.Product Details of 145040-37-5 This article mentions the following:

The present study suggested six different fluorometric systems for the determination of three angiotensin II receptor antagonists, candesartan cilexetil (CDC), valsartan (VAL) and telmisartan (TEL) in their bulk and pharmaceutical dosage forms. The fluorescence intensities (FIs) were recorded by measuring the high catalytic potential activity of silver or gold nanoparticles (AgNPs or AuNPs) at λ_ex 525, 420 and 330 nm and λ_em 555, 490 and 400 nm for CDC, VAL and TEL, resp. All exptl. measurements were carried out under optimum conditions using the CDC-Tb(III)-AgNPs, CDC-Tb(III)-AuNPs, VAL-Eu(III)-AgNPs, VAL-Eu(III)-AuNPs, TEL-SDS-AgNPs and TEL-SDS-AuNPs systems. The fluorescence (FL) signals displayed linear concentration ranges of 0.01-300, 0.02-120 and 2.0-30 ng mL^-1 for CDC, VAL and TEL in the presence of AgNPs, resp., and 0.05-60, 0.1-80 and 0.1-250 ng mL^-1 for the same drugs in the presence of AuNPs, resp. The influence of possible coexisting species and additives was tested. ICH guidelines were followed to validate the developed methods. All suggested FL systems were successfully used to monitor the studied drugs in bulk, tablets and bio-samples. The obtained data were compared with those of other reported methods revealing high agreement. 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: 145040-37-5Product Details 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. 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.Product Details of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Spherical activated carbon modified by polymerized ionic liquid for the removal of ibuprofen from water was written by Xu, Xiao;An, Xiaoning. And the article was included in Journal of Chemical Technology and Biotechnology in 2016.Electric Literature of C9H15F6N2P This article mentions the following:

BACKGROUND: The adsorption capacity of activated carbon has been found to improve through modification with ionic liquids However, ionic liquids tend to sep. from the activated carbon when exposed to water even for a relatively short period. RESULTS: Characterization of spherical activated carbon (SAC) modified with poly(1-vinyl-3-butylimidazolium hexafluorophosphate) (PIL) showed that 1-vinyl-3-butylimidazolium hexafluorophosphate (IL) was adsorbed and polymerized on SAC. Stability studies of PIL-SAC in water demonstrated that it was more stable against IL desorption in water than the non-polymerized IL-SAC. The adsorption data showed that the modification improved the adsorption capacity of SAC at least 2-fold. The results also indicated that although the pH and ionic strength of the solution played a significant role in the adsorption process, there was no significant influence on the adsorption capacity. Moreover, PIL-SAC could be reused at least five times with only minor losses in its adsorption capacity. CONCLUSION : The activated carbon modified with PIL produces a remarkable increase in the ibuprofen adsorption capacity and strongly decreases undesirable desorption of ionic liquids In the experiment, the researchers used many compounds, for example, 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9Electric Literature of C9H15F6N2P).

1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9) 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. 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. Electric Literature of C9H15F6N2P

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Optimised chemical synthesis of 5-substituted UDP-sugars and their evaluation as glycosyltransferase inhibitors was written by Tedaldi, Lauren M.;Pierce, Michael;Wagner, Gerd K.. And the article was included in Carbohydrate Research in 2012.Computed Properties of C4H7ClN2 This article mentions the following:

We have investigated the applicability of different chem. methods for pyrophosphate bond formation to the synthesis of 5-substituted UDP-galactose and UDP-N-acetylglucosamine derivatives The use of phosphoromorpholidate chem., in conjunction with N-methylimidazolium chloride as the promoter, was identified as the most reliable synthetic protocol for the preparation of these non-natural sugar-nucleotides. Under these conditions, the primary synthetic targets 5-iodo UDP-galactose and 5-iodo UDP-N-acetylglucosamine were consistently obtained in isolated yields of 40-43%. Both 5-iodo UDP-sugars were used successfully as substrates in the Suzuki-Miyaura cross-coupling with 5-formylthien-2-ylboronic acid under aqueous conditions. Importantly, 5-iodo UDP-GlcNAc and 5-(5-formylthien-2-yl) UDP-GlcNAc showed moderate inhibitory activity against the GlcNAc transferase GnT-V, providing the first examples for the inhibition of a GlcNAc transferase by a base-modified donor analog. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Computed Properties of C4H7ClN2).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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.Computed Properties of C4H7ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem