Category: imidazoles-derivatives

Radical Cascade Multicomponent Minisci Reactions with Diazo Compounds was written by Su, Yong-Liang;Liu, Geng-Xin;De Angelis, Luca;He, Ru;Al-Sayyed, Ammar;Schanze, Kirk S.;Hu, Wen-Hao;Qiu, Huang;Doyle, Michael P.. And the article was included in ACS Catalysis in 2022.Electric Literature of C8H8N2 This article mentions the following:

Based on the strategy of polarity reversal in the generation of free radicals derived from diazo compounds, R¹C(=N₂)R²[R¹ = ethoxycarbonyl, (benzyloxy)carbonyl, N,N-diethylcarbamoyl, etc.; R² = H, C(O)OMe] photocatalyzed multicomponent reactions (MCRs) of nitrogen aromatic heterocycles, e.g., 4-methylquinoline, alkenes R³CH=CH₂ [R³ = methoxymethyl, cyclohexyl, 4-[(furan-2-yl)carbonyloxy]butyl, etc.], and diazo compounds form functionalized derivatives e.g., Et 4-(4-methylquinolin-2-yl)-6-phenylhexanoate in good to high yields and exacting regioselectivities. The carbon radicals generated from the acceptor diazo compounds are electrophilic, and their selective additions with alkenes provide nucleophilic radicals, which enable the further rapid assembly with various heteroarenes. A delicate balance has been achieved between the activation of heteroarenes through protonation and the decomposition of diazo compounds by the same acid. This multicomponent Minisci reaction shows high functional group tolerance, especially in the incorporation of biol. active mols. Detailed mechanistic studies that include photophys. measurements elaborate this radical cascade reaction. Furthermore, this transformation provides new opportunities for versatile reactions of diazo compounds in radical cascade multicomponent coupling reactions. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Electric Literature of C8H8N2).

1-Methylbenzimidazole (cas: 1632-83-3) 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. 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 C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A Novel Systematic Approach for Selection of Prodrugs Designed to Improve Oral Absorption was written by Shimizu, Mai;Fukami, Tatsuki;Taniguchi, Toshio;Nomura, Yukihiro;Nakajima, Miki. And the article was included in Journal of Pharmaceutical Sciences (Philadelphia, PA, United States) in 2020.COA of Formula: C33H34N6O6 This article mentions the following:

To increase the success rate in development of prodrugs, we sought to establish a systematic in vitro method to appropriately select candidate prodrugs. Physicochem./biopharmaceutical properties of 21 com. available prodrugs (16 with improved membrane permeability of pharmacol. active metabolites and 5 with improved solubility) and their active metabolites were characterized in terms of solubility in artificial intestinal fluids and membrane permeability using Caco-2 cells. Their in vitro metabolic profiles were also evaluated, using human and animal enterocytes, hepatocytes, and sera. Log D values of prodrugs with improved membrane permeability were higher than those of their active metabolites, whereas those of prodrugs with improved aqueous solubility were lower than those of active metabolites. The prodrugs with improved aqueous solubility were highly soluble in artificial intestinal fluids. All prodrugs were efficiently converted to active metabolites with human matrixes, whereas some were not with dog or monkey matrixes. This study demonstrated that physicochem./biopharmaceutical properties could be useful information to facilitate design of prodrugs and for selection of candidate prodrugs. Moreover, the in vitro evaluation of conversion efficiency to active metabolites would be helpful for selecting ideal prodrugs as well as appropriate animals for in vivo PK studies. 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: 145040-37-5COA of Formula: C33H34N6O6).

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. 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 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.COA of Formula: C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

FTIR metabolomic fingerprint reveals different modes of action exerted by active pharmaceutical ingredient based ionic liquids (API-ILs) on Salmonella typhimurium was written by Mester, P.;Jehle, A. K.;Leeb, C.;Kalb, R.;Grunert, T.;Rossmanith, P.. And the article was included in RSC Advances in 2016.HPLC of Formula: 79917-89-8 This article mentions the following:

Since their incorporation into various chem. and biochem. processes, ionic liquids (ILs) have now been found useful for biomedical applications, including active pharmaceutical ingredients (APIs) such as antimicrobial agents or antibiotics. Recently, synergistic API-ILs with great potential have been reported, which show either increased antimicrobial activity or the ability to overcome bacterial resistance. In this study a total of 19 API-ILs, based on the antibiotic nalidixic acid, combined with different cation species, were investigated for synergistic effects against the important foodborne pathogen Salmonella. Furthermore, 19 resp. ILs with chloride as the anion were used to control the effects of the different cation species. The antimicrobial activities of all 38 ILs against six different Salmonella species, as well as two nalidixic acid-resistant S. typhimurium strains, were determined via the microbroth dilution assay. The response pattern of the main cellular constituents, namely proteins, carbohydrates, and lipids of the bacterial cells to the most promising API-ILs was further investigated by Fourier transform IR (FTIR) spectroscopy. While a number of active API-ILs based on nalidixic acid could be synthesized, no evidence for synergistic effects, such as increased antimicrobial activity or the ability to overcome resistance was found with either microbiol. or spectroscopic methods. However, it could be demonstrated for the first time that while the different IL species ([TC₈MA]⁺ and [TMC₁₆A]⁺) showed similar antimicrobial activity, the FTIR spectral patterns indicated changes in bacterial membrane fluidity suggesting different modes of action. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8HPLC of Formula: 79917-89-8).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) 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 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.HPLC of Formula: 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Pharmacophore optimization of imidazole chalcones to modulate microtubule dynamics was written by Karaj, Endri;Dlamini, Samkeliso;Koranne, Radhika;Sindi, Shaimaa H.;Perera, Lalith;Taylor, William R.;Viranga Tillekeratne, L. M.. And the article was included in Bioorganic Chemistry in 2022.Quality Control of 1-(1-Methyl-1H-imidazol-2-yl)ethanone This article mentions the following:

We recently reported a new class of imidazole-based chalcones as potential antimitotic agents. In view of their promising cytotoxic activity, a comprehensive structure-activity relationship (SAR) of these compounds was undertaken focusing on four major structural variations: the length of the mol., the Michael acceptor character, the nature and substitution pattern of ring B, and the nature of the amide functionality tethering ring B. These second-generation analogs (IBCs) demonstrated a superior bioactivity profile than the previously reported imidazole chalcones (referred to as IPEs). The analog IBC-2 with one less methylene group (nor series) and para-fluoro substituted ring B demonstrated the best cytotoxicity profile among the library of compounds A computational anal. of the NCI-60 data associated both IBCs and the previously reported IPEs with the privileged pharmacol. pharmacophore of chalcones. Interestingly, biol. studies suggest that the imidazole ring is essential for cytotoxic activity of the elongated chalcone analogs. Immunofluorescence studies revealed that IBC-2, unlike IPEs, has the ability to induce microtubule catastrophe independently of Aurora-B inhibition. The effects of IBC-2 on microtubule dynamics are similar to those of Nocodazole, but the cell cycle effects appear to be different. In-silico studies demonstrate that the members of the new series have the ability to bind to the colchicine binding site of β-tubulin with binding scores similar to those of IPEs, corresponding chalcones and Nocodazole. Although tubulin binding can partially explain the biol. effects of IBC-2, on-going target identification studies are aimed at further investigation of its biol. targets. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Quality Control of 1-(1-Methyl-1H-imidazol-2-yl)ethanone).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Quality Control of 1-(1-Methyl-1H-imidazol-2-yl)ethanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides was written by Duong, Hung A.;Wu, Wenqin;Teo, Yu-Yuan. And the article was included in Organometallics in 2017.Reference of 25676-75-9 This article mentions the following:

An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields. 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. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Reference of 25676-75-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis, characterization and crystal structure of 1-ferrocenesulfonyl-2-long carbon chain alkyl benzimidazole was written by Zhang, Jun-Zhen;Yang, Bin-Qin;Yang, Ya-Ting;Zhang, Bing-Lin. And the article was included in Yingyong Huaxue in 2007.Product Details of 13060-24-7 This article mentions the following:

Six new 1-ferrocenesulfonyl-2-benzimidazole derivatives were prepared from the reaction of ferrocenesulfonyl chloride with benzimidazole derivatives in the presence of dichloromethane and tetrabutylammonium chloride. The reactions of 2-alkylbenzimidazoles [alkyl = Me(CH₂)_n, n = 5, 6, 7, 8, 10, 14] with ferrocenesulfonyl chloride give 1-ferrocenesulfonyl-2-alkylbenzimidazoles in good yields. The yields of six new ferrocenesulfonyl benzimidazole derivatives were 78-87%. The structures were confirmed by IR, ¹H NMR, elemental anal. and MS. The crystal structure was determined via x-ray single crystal diffraction. The compound 1-ferrocenesulfonyl-2-hexylbenzimidazole is the monoclinic system with space group C2/c, and the unit cell parameters are a = 2.825 2(2) nm, b = 0.976 96(7) nm, c = 1.648 28(12) nm, α = 90°, P = 92.053(2)°, γ = 90°, V = 4.546 6(6) nm³, Z = 8, F(000) = 2 024, M_r = 481.40, D_c = 1.407 g/cm³, μ = 0.784 mm^-1, R₁ = 0.049 5, wR₂ = 0.151 7. In the experiment, the researchers used many compounds, for example, 2-Octylbenzimidazole (cas: 13060-24-7Product Details of 13060-24-7).

2-Octylbenzimidazole (cas: 13060-24-7) 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Product Details of 13060-24-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Free Volume as the Basis of Gas Solubility and Selectivity in Imidazolium-Based Ionic Liquids was written by Shannon, Matthew S.;Tedstone, Jason M.;Danielsen, Scott P. O.;Hindman, Michelle S.;Irvin, A. Christopher;Bara, Jason E.. And the article was included in Industrial & Engineering Chemistry Research in 2012.Product Details of 404001-48-5 This article mentions the following:

While molar volume-based models for gas solubility in ionic liquids (ILs) have been proposed, free volume within the IL can be shown to be the underlying property driving gas solubility and selectivity. Previously published observations as to the distinct differences in solubility trends for gases such as CH₄ and N₂ relative to CO₂ in systematically varied ILs can be attributed to pos. and neg. effects arising from increasing free volume with increasing alkyl chain length. Through the use of COSMOtherm as a powerful and rapid tool to calculate free volumes in 165 existing and theor. 1-n-alkyl-3-methylimidazolium ([C_nmim][X]) ILs, a previously unreported, yet speculated, critical underlying relationship between gas solubility in ILs is herein described. These results build upon previous assertions that Regular Solution Theory is applicable to imidazolium-based ILs, which appeared to indicate that a global maximum had already been observed for CO₂ solubility in imidazolium-based ILs. However, the findings of this computational study suggest that the perceived maximum in CO₂ solubility might be exceeded through rational design of ILs. We observe that although Henry’s constants in ILs are dependent on the inverse of molar volume and free volume, the volume-normalized solubility of CH₄ and N₂ are proportional to free volume, while CO₂ is inversely proportional to the square root of free volume Our free volume model is compared to exptl. data for CO₂/CH₄ and CO₂/N₂ selectivity, and a nearly identical plot of selectivity relative to IL molar volume can be generated from the computational method alone. The overall implication is that large, highly delocalized anions paired with imidazolium cations that have minimally sized alkyl chains may hold the key to achieving greater CO₂ solubility and selectivity in ILs. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Product Details of 404001-48-5).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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.Product Details of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Surface Modification of a Supported Pt Catalyst Using Ionic Liquids for Selective Hydrodeoxygenation of Phenols into Arenes under Mild Conditions was written by Ohta, Hidetoshi;Tobayashi, Kanako;Kuroo, Akihiro;Nakatsuka, Mao;Kobayashi, Hirokazu;Fukuoka, Atsushi;Hamasaka, Go;Uozumi, Yasuhiro;Murayama, Haruno;Tokunaga, Makoto;Hayashi, Minoru. And the article was included in Chemistry – A European Journal in 2019.Recommanded Product: 1-Octyl-1H-imidazole This article mentions the following:

The selective and efficient removal of oxygenated groups from lignin-derived phenols is a critical challenge to utilize lignin as a source for renewable aromatic chems. This report describes how surface modification of a zeolite-supported Pt catalyst using ionic liquids (ILs) remarkably increases selectivity for the hydrodeoxygenation (HDO) of phenols into arenes under mild reaction conditions using atm. pressure H₂. Unmodified Pt/H-ZSM-5 converts phenols into aliphatic species as the major products along with a slight amount of arenes (10 % selectivity). In contrast, the catalyst modified with an IL, 1-butyl-3-methylimidazolium triflate, keeps up to 76 % selectivity for arenes even at a nearly complete conversion of phenols. The IL on the surface of Pt catalyst may offer the adsorption of phenols in an edge-to-face manner onto the surface, thus accelerating the HDO without the ring hydrogenation. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Recommanded Product: 1-Octyl-1H-imidazole).

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. 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. Recommanded Product: 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of methylimidazolium amine ionic liquid for ATRP polymerization system was written by Xue, Teng;Zhou, Jian;Fu, Tantan;Tang, Erjun;Zhao, Dishun. And the article was included in Huagong Xuebao (Chinese Edition) in 2016.Recommanded Product: 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

1-(Pr amine)ethyl-3-Me chloride ionic liquid ([N₂C₃MIM]Cl) was prepared on the base of N-methylimidazole by 1,2-dichloroethane to obtain the intermediates 1-chloro-ethyl-3-Me chloride ionic liquid ([CeMIM]Cl) and then reacting with 1,3-propanediamine. The chem. structure of [N₂C₃MIM]Cl was confirmed by FT-IR and ¹H NMR. [N₂C₃MIM]Cl possessed a lower REDOX potential (-0.522 V) through cyclic voltammetry measurement, [N₂C₃MIM]Cl presented a perfect coordination property compared with organic ligands. The obtained ionic liquid [N₂C₃MIM]Cl coordinated with CuBr was used to catalyze atom transfer radical polymerization (ATRP) of Me methacrylate (MMA) and it indicated by gel permeation chromatog. (GPC) that the coordination ionic liquid [N₂C₃MIM]Cl presented the perfect controllability to the ATRP reactions. The residues of Cu²⁺ in polymerization product PMMA was only 270 mg·kg^-1 by at. absorption spectrometry determination It showed that [N₂C₃MIM]Cl was conducive to the separation of catalyst from the obtained product compared with the traditional organic ligands. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Recommanded Product: 1-Methyl-1H-imidazol-3-ium chloride).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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 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: 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi was written by Wang, Xing;Chen, Yong-Fei;Yan, Wei;Cao, Ling-Ling;Ye, Yong-Hao. And the article was included in Molecules in 2016.Formula: C9H8N2O This article mentions the following:

A series of benzimidazole phenylhydrazone derivatives I (R¹ = H, CH₃, Cl; R² = H, CH₃; R³ = 2,4-F₂, 3,5-Cl₂, 2,6-Cl₂, etc.) was synthesized. The structure of I (R¹ = H; R² = H; R² = 2-F) was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound I (R¹ = H; R² = H; R² = 2,4-F₂) exhibited significant inhibitory activity against R. solani and M. oryzae with the EC₅₀ values of 1.20 and 1.85 μg/mL, resp. In vivo testing demonstrated that I (R¹ = H; R² = H; R² = 2,4-F₂) could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound I (R¹ = H; R² = H; R² = 2,4-F₂) with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Formula: C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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. Formula: C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem