Category: imidazoles-derivatives

In vitro evidence of potential interactions between CYP2C8 and candesartan acyl-β-D-glucuronide in the liver was written by Katsube, Yurie;Tsujimoto, Masayuki;Koide, Hiroyoshi;Hira, Daiki;Ikeda, Yoshito;Minegaki, Tetsuya;Morita, Shin-ya;Terada, Tomohiro;Nishiguchi, Kohshi. And the article was included in Drug Metabolism & Disposition in 2021.Related Products of 145040-37-5 This article mentions the following:

Growing evidence suggests that certain glucuronides function as potent inhibitors of CYP2C8. We previously reported the possibility of drug-drug interactions between candesartan cilexetil and paclitaxel. In this study, we evaluated the effects of candesartan N2-glucuronide and candesartan acyl-β-D-glucuronide on pathways associated with the elimination of paclitaxel, including those involving organic anion-transporting polypeptide (OATP) 1B1, OATP1B3, CYP2C8, and CYP3A4. UDP-glucuronosyltransferase (UGT) 1A10 and UGT2B7 were found to increase candesartan N2-glucuronide and candesartan acyl-β-D-glucuronide formation in a candesartan concentration-dependent manner. Addnl., the uptake of candesartan N2-glucuronide and candesartan acyl-β-D-glucuronide by cells stably expressing OATPs is a saturable process with K_m of 5.11 and 12.1μM for OATP1B1 and 28.8 and 15.7μM for OATP1B3, resp.; both glucuronides exhibit moderate inhibition of OATP1B1/1B3. Moreover, the hydroxylation of paclitaxel was evaluated using recombinant CYP3A4 and CYP3A5. Results show that candesartan, candesartan N2-glucuronide, and candesartan acyl-β-D-glucuronide inhibit the CYP2C8-mediated metabolism of paclitaxel, with candesartan acyl-β-D-glucuronide exhibiting the strongest inhibition (IC₅₀ is 18.9μM for candesartan acyl-β-D-glucuronide, 150μM for candesartan, and 166μM for candesartan N2-glucuronide). However, time-dependent inhibition of CYP2C8 by candesartan acyl-β-D-glucuronide was not observed Conversely, the IC₅₀ values of all the compounds are comparable for CYP3A4. Taken together, these data suggest that candesartan acyl β-D-glucuronide is actively transported by OATPs into hepatocytes, and drug-drug interactions may occur with coadministration of candesartan and CYP2C8 substrates, including paclitaxel, as a result of the inhibition of CYP2C8 function. 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: 145040-37-5Related Products 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. 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.Related Products of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

B-ring modified aurones as promising allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase was written by Meguellati, Amel;Ahmed-Belkacem, Abdelhakim;Yi, Wei;Haudecoeur, Romain;Crouillere, Marie;Brillet, Rozenn;Pawlotsky, Jean-Michel;Boumendjel, Ahcene;Peuchmaur, Marine. And the article was included in European Journal of Medicinal Chemistry in 2014.Related Products of 58442-17-4 This article mentions the following:

Following our recent report showing the potential of naturally occurring aurones (2-benzylidenebenzofuran-3(2H)-ones) as anti-hepatitis C virus (HCV) agents, efforts were continued in order to refine the structural requirements for the inhibitory effect on HCV RNA-dependent RNA polymerase (RdRp). In this study, we targeted the B-ring moiety of aurones with the aim to improve structural features associated with higher inhibition of the targeted polymerase. In vitro evaluation of the RdRp inhibitory activity of the 37 newly synthesized compounds pointed out that the replacement of the B-ring with an N-substituted indole moiety induced the highest inhibitory effect. Of these, compounds 31, 40 and 41 were found to be the most active (IC₅₀ = 2.3-2.4 μM). Docking experiments performed with the most active compounds revealed that the allosteric thumb pocket I of RdRp is the binding pocket for aurone analogs. In the experiment, the researchers used many compounds, for example, 1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4Related Products of 58442-17-4).

1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4) 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Related Products of 58442-17-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Influence of the alkyl side chain length on the thermophysical properties of chiral ionic liquids with a (1R,2S,5R)-(-)-menthol substituent and data analysis by means of mathematical gnostics was written by Andresova, Adela;Bendova, Magdalena;Schwarz, Jaroslav;Wagner, Zdenek;Feder-Kubis, Joanna. And the article was included in Journal of Molecular Liquids in 2017.Quality Control of 1-Octyl-1H-imidazole This article mentions the following:

A comprehensive physico-chem. characterization of the chiral ionic liquids of a 3-alkyl-1-[(1R,2S,5R)-(-)-menthoxymethyl]imidazolium bis(trifluoromethylsulfonyl)imides homologous series with a linear alkyl substituent ranging from the Me up to the dodecyl group was carried out exptl. to investigate the way in which the measured thermophys. properties were influenced by the alkyl chain length on the cation. Refractive index, d., speed of sound, and isobaric heat capacity were measured as a function of temperature at atm. pressure and analyzed by methods based on math. gnostics. A robust linear regression along a gnostic influence function was used to optimize parameters of the relationships used in this work and to estimate the changing nanosegregation in the studied ionic liquid series by finding the Critical Alkyl Length Size (CALS) from heat capacity data. In addition, we propose the use of the marginal anal. to assess the quality of the measured data as an alternative to the estimate of the measurement uncertainty. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Quality Control of 1-Octyl-1H-imidazole).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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.Quality Control of 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Syntheses of formamidines and benzimidazoles was written by Mathias, L. J.;Overberger, C. G.. And the article was included in Synthetic Communications in 1975.Category: imidazoles-derivatives This article mentions the following:

The benzimidazoles I (R = 5(6)-Cl, 5(6)-Me, 5(6)-CO2H, 5(6)-benzimidazol-5(6)-yl) were prepared by cyclization of 4-RC6H3(NH2)2-1,2 with HCO2H in the presence of HCl and a strong acid resin. RNHCH:NR (R = p-O2NC6H4, p-H2NC6H4, 2-thiazolyl, 2-pyridyl) and I (R = 5(6)-Me, 4(7)-Me, 5(6)-NO2, 5(6)-COMe, 5(6)-CHO, 5(6)-Cl) were prepared by treating RNH2 or RC6H4(NH2)2-1,2 with Cl2CHOMe containing (Me3C)3N. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Category: imidazoles-derivatives).

7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Effect of the alkyl chain length in 1-alkyl-3-methylimidazolium ionic liquids on inter-molecular interactions and rotational dynamics was written by Garaga, Mounesha N.;Nayeri, Moheb;Martinelli, Anna. And the article was included in Journal of Molecular Liquids in 2015.Application of 404001-48-5 This article mentions the following:

We have investigated the effect of increasing the alkyl chain length, n, in 1-alkyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide (C_nC₁ImTFSI) ionic liquids on both inter-mol. interactions and rotational dynamics. This has been addressed by combining 1D ¹H and T₁ relaxation NMR spectroscopy with vibrational spectroscopy, including both Raman and IR. We find that the vibrational modes sensitive to inter-mol. interactions change only slightly with an increased alkyl chain length, with negligible changes for chains longer than the hexyl (n > 6). This is nicely corroborated by ¹H chem. shift changes, in particular of the aromatic protons. The ¹³C correlation times, τ_c, of the individual carbon atoms reveal that while the overall rotational mobility decreases with n, different dynamical properties are observed with the polar domains becoming the most dynamic and the imidazolium ring and its closest chain segment the most rigid. We conclude that the formation of segregated nano-domains in C_nC₁ImTFSI is accompanied by the formation of nano-dynamical heterogeneities, which can explain why classical theories fail to describe the dependence on n of macroscopically observed properties. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Application of 404001-48-5).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Application of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Isonucleosides incorporating universal bases was written by Nair, Vasu;Sosnouski, David S.;Zhu, Qingming. And the article was included in Nucleosides, Nucleotides & Nucleic Acids in 2001.Related Products of 26832-08-6 This article mentions the following:

Enantiomeric isodideoxynucleosides of the (S,S) and (R,R) families with the universal base, imidazole-4-carboxamide as the nucleobase, were synthesized as biol. mimics of anti-HIV active D– and L-related isodideoxyadenosines. In vitro anti-HIV evaluation in CEM cells of these target compounds showed that they were inactive. Further antiviral studies are in progress. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Related Products of 26832-08-6).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Related Products of 26832-08-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Small nickel nanoparticle arrays from long chain imidazolium ionic liquids was written by Yang, Mei;Campbell, Paul S.;Santini, Catherine C.;Mudring, Anja-Verena. And the article was included in Nanoscale in 2014.SDS of cas: 404001-48-5 This article mentions the following:

Six long chain alkyl mono- and bi-cationic imidazolium based salts with bis(trifluoromethylsulfonyl)imide (NTf₂^–) as the anion were synthesized and characterized. The single crystal structure of 1-methyl-3-octadecylimidazolium bis(trifluoromethylsulfonyl)imide could be obtained by x-ray anal. All these long chain alkyl imidazolium based ILs were applied in the synthesis of Ni nanoparticles via chem. decomposition of an organometallic precursor of Ni. In these media, spontaneous decomposition of Ni(COD)₂ (COD = 1,5-cyclooctadiene) in the absence of H₂ occurred giving small NPs (â‰? nm) with narrow size distributions. Formation of regularly interspaced NP arrays was also observed in long chain ILs. Such array formation could be interesting for potential applications such as C nanotube growth. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5SDS of cas: 404001-48-5).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Protic Ionic-Liquid-Supported Activated Carbon with Hierarchical Pores for Efficient NH₃ Adsorption was written by Yu, Min;Zeng, Shaojuan;Wang, Zongxu;Hu, Zongyuan;Dong, Haifeng;Nie, Yi;Ren, Baozeng;Zhang, Xiangping. And the article was included in ACS Sustainable Chemistry & Engineering in 2019.Quality Control of 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

Ionic liquids (ILs) provide a new way for efficient separation and recovery of NH₃ because of low vapor pressure and adjustable properties. However, high viscosity or solid state of functionalized ILs at ambient temperature makes them impossible to use in traditional scrubbing processes. Therefore, combining ILs with porous solid materials to form novel IL-supported materials for NH₃ adsorption is an effective method to solve the above problem. In this work, three protic ILs (PILs) including imidazolium bis(trifluoromethylsulfonyl)imide ([Im][NTf₂]), 1-methylimidazolium bis(trifluoromethylsulfonyl)imide ([1-Mim][NTf₂]), and 2-methylimidazolium bis(trifluoromethylsulfonyl)imide ([2-Mim][NTf₂]) were supported onto activated carbon (AC) to prepare PIL-supported materials. The effects of PILs and AC types, PIL loadings, temperatures, and partial pressures on NH₃ adsorption, as well as the recyclability of the PIL-supported materials, were investigated in detail. Among the investigated PIL-supported materials, 20 weight % [2-Mim][NTf₂]-supported AC-980 exhibits the higher capacity of 68.61 mg of NH₃/g of adsorbent at 303.15 K and 0.10 MPa with good NH₃ selectivity and fast adsorption rate because of the synergistic interaction of hydrogen bonding between the PIL and NH₃ and hierarchical pores, which is 30% higher than that of pure AC. Meanwhile, the PIL-supported material shows good recyclability after five cycles, implying great potentials for NH₃ separation industrial processes. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Quality Control of 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Quality Control of 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Developing the {M(CO)₃}⁺ Core for Fluorescence Applications: Rhenium Tricarbonyl Core Complexes with Benzimidazole, Quinoline, and Tryptophan Derivatives was written by Wei, Lihui;Babich, John W.;Ouellette, Wayne;Zubieta, Jon. And the article was included in Inorganic Chemistry in 2006.Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

Tridentate ligands derived from benzimidazole, quinoline, and tryptophan were synthesized, and their reactions with [NEt₄]₂[Re(CO)₃Br₃] were studied. [Re(CO)₃L]Br (L = L1, L2, L3, L4, L6, L7) (1–4, 6 and 7) exhibit fac-{Re(CO)₃N₃} coordination geometry in the cationic mol. units, while [Re(CO)₃L]Br (L = L5) (5) exhibits fac-{Re(CO)₃N₂O} coordination for the neutral mol. unit, where N₃ and N₂O refer to the ligand donor groups. The ligands bis(1-methyl-1H-benzoimidazol-2-ylmethyl)amine (L1), [bis(1-methyl-1H-benzoimidazol-2-ylmethyl)amino]acetic acid Et ester (L2), [bis(1-methyl-1H-benzoimidazol-2-ylmethyl)amino]acetic acid Me ester (L3), [bis(quinolin-2-ylmethyl)amino]acetic acid Me ester (L4), 3-(1-methyl-1H-indol-3-yl)-2-[(pyridin-2-ylmethyl)amino]propionic acid (L5), 2-[bis(pyridin-2-ylmethyl)amino]-3-(1-methyl-1H-indol-3-yl)propionic acid (L6), and 2-[bis(quinolin-2-ylmethyl)amino]-3-(1-methyl-1H-indol-3-yl)propionic acid (L7) were obtained in good yields and characterized by elemental anal., 1-dimensional and 2-dimensional NMR, and high-resolution mass spectrometry (HRMS). The Re complexes were obtained in 70-85% yields and characterized by elemental anal., 1-dimensional and 2-dimensional NMR, HRMS, IR, UV, and luminescence spectroscopy, as well as x-ray crystallog. for [Re(CO)₃(L1)]Br (1), {[Re(CO)₃(L2)]Br}₂·NEt₄Br·8.5H₂O (3₂·NEt₄Br·8.5H₂O), [Re(CO)₃(L4)]Br (4), and [Re(CO)₃(L6)]Br (6). Crystal data for C₂₁H₁₉BrN₅O₃Re (1): monoclinic, space group P2₁/c, a 13.1851(5), b 16.1292(7), c 10.2689(4) Å, β 99.353(1)°, Z = 4. Crystal data for C₅₆H₇₃Br₃N₁₁O_18.50Re₂ (3₂·NEt₄Br·8.5H₂O): monoclinic, space group C2/c, a 34.7760(19), b 21.1711(12), c 20.3376(11) Å, β 115.944(1)°, Z = 8. Crystal data for C₂₆H₂₁BrN₃O₅Re (4): monoclinic, space group P2₁/c, a 16.6504(6), b 10.1564(4), c 14.6954(5) Å, β 96.739(1)°, Z = 4. Crystal data for C₂₇H₂₄BrN₄O₅Re (6): monoclinic, space group P2₁, a 8.7791(9), b 16.312(2), c 8.9231(9) Å, β 90.030(1)°, Z = 2. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Name: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

NMR Quantification of Hydrogen-Bond-Accepting Ability for Organic Molecules was written by Milic, Mira;Targos, Karina;Tellez Chavez, Magda;Thompson, Madison A. M.;Jennings, Julia J.;Franz, Annaliese K.. And the article was included in Journal of Organic Chemistry in 2021.SDS of cas: 1632-83-3 This article mentions the following:

The hydrogen-bond-accepting abilities for more than 100 organic mols. are quantified using ¹⁹F and ³¹P NMR spectroscopy with pentafluorobenzoic acid (PFBA) and phenylphosphinic acid (PPA) as com. available, inexpensive probes. Anal. of pyridines and anilines with a variety of electronic modifications demonstrates that changes in NMR shifts can predict the secondary effects that contribute to H-bond-accepting ability, establishing the ability of PFBA and PPA binding to predict electronic trends. The H-bond-accepting abilities of various metal-chelating ligands and organocatalysts are also quantified. The measured Δδ(³¹P) and Δδ_p(¹⁹F) values correlate strongly with Hammett parameters, pK_a of the protonated HBA, and proton-transfer basicity (pK_BH+). In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3SDS of cas: 1632-83-3).

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. 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.SDS of cas: 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem