Imidazoles-derivatives

Reactions of 2-dichloromethylbenzimidazole with certain primary amines was written by Pascal, Robert A. Jr.;Jungk, Steven;Risinger, G. E.. And the article was included in Journal of Heterocyclic Chemistry in 1978.Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

An investigation of the reactions of 2-(2,2-dichloromethyl)benzimidazole (I) with primary amines gave 2-(N–tert-butylformimidoyl)benzimidazole, 2-N-(2-phenylethyl)formimdoylbenzimidazole, and 1-(ethoxycarbonylmethyl)-2-(N–tert-butylformimidoyl)benzimidazole. Under mild alkali conditions, I was rapidly converted into a dimer, 6H,13H-pyrazino[1,2-a:4,5-a‘]bisbenzimidazole-6,13-diol. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and Antimicrobial Activity of Nitroalkenyl Arenes was written by Nicoletti, Gina;Cornell, Hugh James;Hugel, Helmut Martin;White, Kylie S.;Nguyen, Thu;Zalizniak, Liliana;Nugegoda, Dayanthi. And the article was included in Anti-Infective Agents in 2013.Reference of 58442-17-4 This article mentions the following:

We report here on the synthesis of substituted nitroalkenyl arenes and their evaluation for microbiol. activity and for development as anti-infective drugs. Twenty compounds, based on the nitropropenyl benzene structure (1), were synthesized, chem. characterized and investigated for their min. inhibitory concentration (MIC) to bacteria and fungi and for toxicity to zebrafish eggs and embryos for comparative evaluation of potential mammalian toxicity. The compounds were broadly antimicrobial, with greater activity overall against Gram-pos. bacteria and fungi and less against enteric Gram-neg. rods. The antimicrobial activity spectrum of the compounds varied greatly. Two compounds, 14 (5-[(E)-2-nitroprop-1-enyl]-1,3-benzodioxole) and 9 (4-[(E)-2-nitroprop-1-enyl]-1-fluorobenzene), were the most broadly antimicrobial. The chem. groups most closely associated with microbial toxicity were the β-nitropropenyl side chain, fluoro, methylenedioxy and thiazole substitutions on the benzene ring. Thirteen compounds inhibited hatching of zebrafish eggs at concentrations ≤6 μg/mL. Egg toxicity did not correlate with inhibition of microbial growth or with rodent toxicity where data were available. Four compounds were investigated for effect on zebrafish embryonic development. The major effect observed was reduction of heart rate at 24 h with minimal or no morphol. abnormalities at the highest doses. It is hypothesised that this series of compounds act as tyrosine mimetics, inhibiting protein tyrosine phosphatases (PTP) and interfering with cell signaling in microorganisms. The data confirms the diversity in function and distribution of bacterial PTPs and the potential for the design of further nitroalkenyl arenes active against specific pathogens. In the experiment, the researchers used many compounds, for example, 1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4Reference of 58442-17-4).

1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4) 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.Reference of 58442-17-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Antiviral activity of the FDA-approved drug candesartan cilexetil against Zika virus infection was written by Loe, Marcus Wing Choy;Lee, Regina Ching Hua;Chu, Justin Jang Hann. And the article was included in Antiviral Research in 2019.Name: 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 This article mentions the following:

Zika virus (ZIKV) is a mosquito-borne virus that has risen to prominence as a significant threat to public health in the recent decade. Since its re-emergence in 2007, ZIKV has spread at an alarming rate and has since become endemic to multiple regions around the world. Infections are primarily asymptomatic, however the virus has become associated with the development of severe neurol. complications such as Guillain-Barre syndrome (GBS) and congenital microcephaly. At present, there are currently no approved antivirals for ZIKV infections. In this study, we utilized a phenotype-based screening platform to perform a high-throughput screen on a 1172-compound US FDA-approved drug library to identify potential novel inhibitors against ZIKV. Candesartan cilexetil, an angiotensin II receptor inhibitor, displayed potent inhibition effects against ZIKV and subsequent downstream time-course studies revealed that it targets a post-entry stage(s) of the ZIKV replication cycle. Moreover, candesartan cilexetil also inhibited viral RNA production and viral protein synthesis. Candesartan cilexetil also exhibited antiviral effects against Dengue virus serotype-2 (DENV2), Kunjin virus (KUNV) and Chikungunya virus (CHIKV), indicating that its antiviral properties may not be restricted to ZIKV. Our study has demonstrated for the first time the potential application of candesartan cilexetil as an antiviral. 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: 145040-37-5Name: 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).

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. 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. Name: 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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Energetic Contributions from the Cation and Anion to the Stability of Carbon Dioxide Dissolved in Imidazolium-Based Ionic Liquids was written by Ishizuka, Ryosuke;Matubayasi, Nobuyuki;Tu, Kai-Min;Umebayashi, Yasuhiro. And the article was included in Journal of Physical Chemistry B in 2015.Application of 404001-48-5 This article mentions the following:

Cation and anion effects were investigated in the energetics of CO₂ solvation in room-temperature ionic liquids The solvation free energy in 1-n-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([C₄mim][NTf₂]) was calculated with three types of force fields by mol. dynamics simulations combined with the energy-representation (ER) method, and the interaction responsible for the CO₂ stability was examined in terms of the average sum of the solute-solvent interaction energy and its electrostatic and van der Waals components. A key role of the van der Waals component was found for the cation contribution, and the electrostatic component was seen to be minor in the anion contribution. The solvation free energy of CO₂ was also investigated in 1-n-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([C_nmim][NTf₂]) ionic liquids with n = 4, 6, 8, and 12 by the ER method. The free energy was found to depend weakly on n, in agreement with experiments, and the cation and anion contributions and the electrostatic and van der Waals interaction components acted similarly at all values of n examined The alkyl-chain length was found not to affect the local structure around CO₂ strongly, and its effect on the interaction energy with CO₂ appeared mainly through the bulk d. 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. 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.Application of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ethyl 3-methyl-5-nitro-1H-imidazole-2-carboxylate was written by Wu, Hai Qiang;An, Lin Kun;Huang, Zhi Shu;Gu, Lian Quan;Zain, Sharifuddin M.;Ng, Seik Weng. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2004.Application In Synthesis of Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate This article mentions the following:

The title compound, C₇H₉N₃O₄, exists as a planar mol. whose carboxyethyl fragment is disordered across a crystallog. mirror plane. The fragment is twisted by 15.1(1)° with respect to the plane. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 109012-23-9Application In Synthesis of Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate).

Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 109012-23-9) 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Application In Synthesis of Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Design and synthesis of pinanamine derivatives as anti-influenza A M2 ion channel inhibitors was written by Zhao, Xin;Jie, Yanling;Rosenberg, Matthew R.;Wan, Junting;Zeng, Shaogao;Cui, Wei;Xiao, Yiping;Li, Zhiyuan;Tu, Zhengchao;Casarotto, Marco G.;Hu, Wenhui. And the article was included in Antiviral Research in 2012.Related Products of 3012-80-4 This article mentions the following:

The adamantanes are a class of anti-influenza drugs that inhibit the M2 ion channel of the influenza A virus. However recently, the clin. effectiveness of these drugs has been called into question due to the emergence of adamantane-insensitive A/M2 mutants. Although we previously reported (1R,2R,3R,5S)-3-pinanamine 3 as a novel inhibitor of the wild type influenza A virus M2 protein (WT A/M2), limited inhibition was found for adamantane-resistant M2 mutants. In this study, we explored whether newly synthesized pinanamine derivatives were capable of inhibiting WT A/M2 and selected adamantane-resistant M2 mutants. Several imidazole and guanazole derivatives of pinanamine were found to inhibit WT A/M2 to a comparable degree as amantadine and one of these compounds 12 exhibits weak inhibition of A/M2-S31N mutant and it is marginally more effective in inhibiting S31N M2 than amantadine. This study provides a new insight into the structural nature of drugs required to inhibit WT A/M2 and its mutants. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Related Products of 3012-80-4).

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

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Structure of protic (HC_nImNTf₂, n = 0-12) and aprotic (C₁C_nImNTf₂, n = 1-12) imidazolium ionic liquids: A vibrational spectroscopic study was written by Moschovi, Anastasia Maria;Dracopoulos, Vassileios. And the article was included in Journal of Molecular Liquids in 2015.Recommanded Product: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

The interactions of alkyl substituted imidazolium bis(trifluoromethanesulfonyl)imide protic (PILs) HC_nImNTf₂ (n = 0-12) and aprotic ionic liquids (APILs) C₁C_nNTf₂ (n = 1-12) were studied using vibrational spectroscopy (FT-IR/ATR and FT-Raman). The effect of alkyl substituent length (n = 0-12) on both polar and non-polar regions is elucidated. A sponge like structure is proposed for both systems. The spectral characteristics show that there are certain structural differences between PILs and APILs. The well defined hydrogen bonding in PILs strongly affects the local structure of both the polar head (i.e., induction effect) and the side alkyl chain. The spectral findings tentatively suggest that nanosegregation occurs at shorter alkyl chains. In APILs the data correlated with the polar and non-polar regions are discussed on the basis of the proposed sponge like structure. The trans/cis ratio of the anion conformers is related to the dispersion of the average position of the anion over the cation. Also in the oily phase the local structure of the side chain shows certain differences compared to PIL systems. A tail coupling occurred (up to eight carbon atom alkyls) followed by decoupling in higher length tails in APILs indicating an increase of van der Waals forces between the chains. Moreover, we show that the enthalpy of conformational isomerism of the anion is also a good indicator in the case of APILs, regarding the relative magnitude of these interactions. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Recommanded Product: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide).

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 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: 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and Surface Properties of Novel Gemini Imidazolium Surfactants was written by Wang, Liyan;Liu, Jia;Huo, Shichao;Deng, Qigang;Yan, Tie;Ding, Limin;Zhang, Chao;Meng, Lingwei;Lu, Qiangna. And the article was included in Journal of Surfactants and Detergents in 2014.Electric Literature of C11H20N2 This article mentions the following:

Five new Gemini imidazolium surfactants were synthesized from imidazole and 1-bromoalkane (C₈, C₁₀, C₁₂, C₁₄, C₁₆) to get 1-alkylimidazole, which was further reacted with 1,3-dichloropropan-2-ol to form the surfactant mol., 1,1′-(propane-1,3-diyl-2-ol) bis(3-alkyl-1H-imidazol-3-ium) chloride. The structures of the five new surfactants and intermediates were characterized by ¹H-NMR, ¹³C-NMR and IR spectra. Thermal properties of the five new surfactants were studied with thermogravimetric anal. and differential scanning calorimetry, the five new surfactants showed a transition from a crystalline phase to a thermotropic liquid-crystalline phase at around ca. 100 °C, which transformed to an isotropic liquid phase at around ca. 165 °C. The five new surfactants critical micelle concentrations (CMC) in the aqueous solutions were determined by surface tension and elec. conductivity methods. The surface tension measurements provided a series of parameters, including critical micelle concentration (CMC), surface tension at the CMC (γ_CMC), adsorption efficiency (pC₂₀), and effectiveness of surface tension reduction (π_CMC). In addition, with application of the Gibbs adsorption isotherm, maximum surface excess concentration (Γ_max) and min. surface area/mol. (A_min) at the air-water interface were obtained. The parameters β (degree of counterion binding to micelles), ΔG^θ_ads (Gibbs free energy of adsorption), and ΔG^θ_mic (Gibbs free energy change of micellization) were also derived. The results indicated that the five new Gemini surfactants exhibited very low CMC and a good efficiency in lowering the surface tension of water. The foamability and foam stability of the five new surfactants were also examined at different CMC. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Electric Literature of C11H20N2).

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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Electric Literature of C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Interactions in aqueous solutions of imidazolium chloride ionic liquids [C_nmim][Cl] (n=0, 1, 2, 4, 6, 8) from volumetric properties, viscosity B-coefficients and molecular dynamics simulations was written by Tomas, Renato;Tot, Aleksandar;Kuhar, Jure;Bester-Rogac, Marija. And the article was included in Journal of Molecular Liquids in 2018.Product Details of 35487-17-3 This article mentions the following:

In this work a systematic study of aqueous diluted solutions (~0.005 < m/mol/kg < ~0.1) of six imidazolium based ionic liquids (IL) [C_nmim][Cl] with different alkyl chain lengths (n=0, 1, 2, 4, 6, 8) was carried out. Densities and viscosities were measured as a function of IL concentration in the temperature range between 278.15K and 313.15K in steps of 5K. From exptl. data, apparent molar volumes, standard partial molar volumes, and viscosity B-coefficients of ILs were derived. The effect of the alkyl chain length on the estimated properties was discussed in terms of ion-ion and ion-solvent interactions. It turned out that the studied cations with longer alkyl side chain (n=4, 6, 8) can be regarded as structure makers; cations with shortest side chain (n=0, 1) as structure breakers, whereas [C₂mim]⁺ can be considered as a border line ion. In order to obtain more information about interactions and influence of studied ILs on water structure, computational simulations were performed. For this purpose, DFT calculations using B3LYP-D3 functional and mol. dynamic simulations with OPLS 2005 force field, were applied. Obtained results show that the increase in length of alkyl substituent in imidazolium ring leads to weakening of interactions with water mols. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Product Details of 35487-17-3).

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 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).Product Details of 35487-17-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Study on the synthesis and structure-effect relationship of multi-aryl imidazoles with their fluorescence properties was written by Tian, Mi;Wang, Chao;Wang, Li Gong;Luo, Kai;Zhao, An;Guo, Can Cheng. And the article was included in Luminescence in 2014.Recommanded Product: 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid This article mentions the following:

The 23 multi-aryl imidazole derivatives I and II (R = Me, MeO, O₂N, etc.) were synthesized and identified by NMR, UV-visible and elemental anal. At the same time, their UV-visible maximum absorption (λ_ab^max), fluorescence emission maximum (λ_em^max) and quantum yields (Φ_f) were measured. The relationships between the optical behaviors and structures for these compounds were assessed. The results show that the λ_ab^max and λ^maxem are red-shifted and the fluorescence Φ_f are increased by the introduction of electron-withdrawing substituents and the increase in the planarity of multi-aryl imidazole mols. The results also showed that the fluorescence quantum yields of the compounds containing two imidazole nuclei are double the corresponding mono-imidazole nucleus compounds In the experiment, the researchers used many compounds, for example, 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid (cas: 5496-35-5Recommanded Product: 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid).

4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid (cas: 5496-35-5) 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.Recommanded Product: 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem