Category: imidazoles-derivatives

Song, Xiangbo published the artcileA highly effective approach to enhance the performance of biomass-derived acid for fructose conversion to 5-hydroxymethylfurfural, Product Details of C8H15ClN2, the publication is Fuel Processing Technology (2022), 107318, database is CAplus.

Synthesis of 5-hydroxymethylfurfural (HMF) from carbohydrate is one of vital step for bio-refinery development. In this work, a novel strategy was developed for catalytic conversion of fructose to HMF in 2-butanol. The inexpensive ionic liquids were used to adjust the acidity of biobased acid catalyst for enhancing the dehydration of fructose to HMF. The combination of 1-butyl-3-methylimidazolium chloride ([Bmim]Cl) with oxalic acid afforded an excellent HMF yield of 97.1% at 98.7% fructose conversion under mild conditions of 100°C and 60 min, owing to the enhanced dissociation ability of oxalic acid by [Bmim]Cl. A possible dissociation mechanism of oxalic acid induced by [Bmim]Cl was proposed based on control experiments and detailed analyses with NMR and FT-IR techniques. It involved that the [Bmim]Cl interacted with oxalic acid through hydrogen bond, which decreased the electron d. of oxygen atom on hydroxyl group and weakened the O-H bond, thus making the hydrogen in the O-H group to easily dissociate in the form of H⁺. Moreover, the reusability of oxalic acid and [Bmim]Cl was demonstrated, and both could be reused up to six times without significant loss in activity.

Fuel Processing Technology published new progress about 79917-90-1. 79917-90-1 belongs to imidazoles-derivatives, auxiliary class Ionic Liquid,Ionic Liquid, name is 3-Butyl-1-methyl-1H-imidazol-3-ium chloride, and the molecular formula is C12H10F2Si, Product Details of C8H15ClN2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Qian, He-Sheng published the artcileAnalysis of pyrolyzates for polysulphoneamide fiber by Py-GC/MS, Related Products of imidazoles-derivatives, the publication is Journal of Donghua University (2006), 23(2), 63-67, database is CAplus.

Pyrolysis of polysulfoneamide fiber has been investigated using pyrolysis gas chromatog.-mass spectroscopy at the different temperatures from 420°C to 750°C. Its compositions of pyrolyzates have been analyzed. At 420°C, pyrolysis of mol. chain could not completely take place, 12 compounds of pyrolysis have only been identified. When the temperature increases, the compositions of pyrolyzate increase sharply. Several compounds, especially sulfur dioxide, benzene, aniline, benzoic acid, 1,4-benzene dicaronitrile, N-phenyl-acetamide, diphenylamine, benzo[g]isoquinoline, N-phenyl-benzamide, N-(4-cyanophenyl)benzamide, could be formed. The degradation mechanisms which are determined by structure and amount of the thermal decomposition products are described. During pyrolysis, for polysulfoneamide, polymeric chain scissions take place as a successive removal of the monomer units from the polymeric chain. The chain scissions are followed by secondary reactions, which lead to a variety of compounds Addnl. reactions can also take place during pyrolysis.

Journal of Donghua University published new progress about 2622-67-5. 2622-67-5 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Benzene,Benzimidazole, name is 1,2-Diphenyl-1H-benzo[d]imidazole, and the molecular formula is C19H14N2, Related Products of imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Lee, Jyun-Ting published the artcileHigh-efficiency cycling piezo-degradation of organic pollutants over three liters using MoS₂ /carbon fiber piezocatalytic filter, Quality Control of 79917-90-1, the publication is Nano Energy (2022), 107280, database is CAplus.

Piezocatalysis has great potential com. application for the high-efficiency degradation of organic pollutants in a dark environment. However, the recycling of catalyst materials and the subsequent generation of secondary pollution remain challenging. In this study, MoS₂ nanoflowers (NFs)/carbon fiber was synthesized to develop a piezocatalytic filter that can recycle decomposed wastewater easily without generating secondary pollutants in treated water. The MoS₂/carbon fiber was constructed in pipelines to form the piezoelec. degradation system, which demonstrated a high efficiency in decomposing organic mols. in wastewater through natural water flow. The piezocatalytic filters in the circulatory system completely degraded a large amount of dye solution (1000 mL) in 40 min and can repeat three-times degradation with the total organic carbon value decreased by 90%. The theor. calculation indicated that MoS₂ grew on carbon fiber, which exhibited a bending moment effect under natural water-flow-induced pressure. This established considerable piezoelec. potential at MoS₂ NFs active edge sites and MoS₂-carbon fiber interfaces, triggering electron-hole pair separation under the internal elec. field. The MoS₂/carbon fiber piezoelec. catalyst is advantageous for its reusability and recyclability, thus preventing secondary pollution and adverse effects on water bodies during practical high-flux wastewater treatment.

Nano Energy published new progress about 79917-90-1. 79917-90-1 belongs to imidazoles-derivatives, auxiliary class Ionic Liquid,Ionic Liquid, name is 3-Butyl-1-methyl-1H-imidazol-3-ium chloride, and the molecular formula is C8H15ClN2, Quality Control of 79917-90-1.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Hughes, Gordon K. published the artcileThe synthesis of 2-aminomethylbenziminazole and related substances, Name: (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, the publication is Journal and Proceedings of the Royal Society of New South Wales (1938), 209-22, database is CAplus.

It appeared that 2-aminomethylbenziminazole (I) might prove worthy of investigation as a base for study of coordination problems, because the imino H of the benziminazole nucleus can be replaced by metals (cf. Bamberger and Lorenzen, Ann. 273, 271-9(1893)). Stable metallic complex compounds in which a central bivalent metallic element is bound to 2-aminomethylbenziminazole nucleii by 2 electrovalences and 2 coördination covalences should thus be obtainable. Synthesis of I was not easy; glycine could not be made to condense with o-(NH₂)₂C₆H₄ (II) according to the method of M. A. Phillips (cf. C. A. 23, 141). A method of preparation of I was therefore developed from 2-chloromethylbenziminazole (III), m. 160-1°, which was prepared in the following manner: 22 g. II and 20 g. ClCH₂CO₂H in 200 cc. 4 N HCl were refluxed for 40 min., and after filtering and cooling, the solution was neutralized with Na₂CO₃, giving a white solid which was recrystallized from EtOH and AcOEt. A better method for preparing III consisted in treating 2-hydroxymethylbenziminazole (IV) (Phillips, loc. cit.) with SOCl₂; yield, 71%. Various attempts to replace the Cl atom in III with an NH₂ group by means of NH₃ solutions were unsuccessful, the reaction being quite complex and yielding several substances. From III, the following benziminazole derivatives were prepd: from Me anthranilate, 2-o-carbomethoxyanilinomethyl, yellow, m. 216°; from PhNHMe, 2-methylanilinomethyl, yellow, m. 202°; from Ph₂NH, 2-diphenylaminomethyl, colorless, m. 215°; from (CH₂)₅NH, 2-piperidinomethyl, colorless, m. 193-4° (with previous softening at 180°); from morpholine, 2-morpholinomethyl, colorless, m. 211°; with C₅H₅N, III reacted violently giving a white solid which is probably a quaternary salt. IV and Me₂SO₄ gave 1-methyl-2-hydroxymethylbenziminazole, m. 105°, which with SOCl₂ yielded 1-methyl-2-chloromethylbenziminazole, m. 94°; the latter with PhNH₂ and PhNHMe gave 1-methyl-2-anilino-, m. 118°, and 1-methyl-2-methylanilinomethylbenziminazole, m. 145°, resp. Fusion of phenylglycine (3 g.) with II (2 g.) yielded 2-anilinomethylbenziminazole, m. 162°, which could not be prepared from III and PhNH₂. Fusion of phthalimidoacetic acid with II gave a white amorphous product containing no O and whose structure is not known. Fusion of equimol. quantities of hippuric acid and II gave 70% 2-benzoylaminomethylbenziminazole, m. 231°, which (33 g.) was hydrolyzed with concentrated HCl (75 cc.) for 5 h. to the di-HCl salt of I as a monohydrate which loses H₂O at 110°, giving an anhydrous salt, m. 263°. Attempts to isolate anhydrous I gave only brown gums; however, careful neutralization with Na₂CO₃ gave a hydrate, m. 53°; 2-acetylamino derivative, m. 200°. Condensation of HSCH₂CO₂H and II (50 g.) in 500 cc. 4 N HCl with heating for 60 min. gave 50 g. 2-sulfhydrylmethylbenziminazole (V), m. 158°; passage of air through an NH₃ solution of the latter is sufficient to oxidize it to a compound, C₁₆H₁₄O₂N₄S₂, m. 182°, which is probably the disulfoxide of V and which was also obtained by oxidation of V with dilute HNO₃. The following benziminazole derivatives were obtained from II, using Phillips’ method: from phenoxyacetic acid, 2-phenoxymethyl, white, m. 162°; from methoxyacetic acid, 2-methoxymethyl, yellow, m. 136°; from phenylacetic acid, 2-benzyl, colorless, m. 187°; from β-phenylpropionic acid, 2-β-phenylethyl, colorless, m. 186°; from p-nitrophenylacetic acid, 2-p-nitrobenzyl, yellow, m. 215°; from o-nitrophenylacetic acid, 2-o-nitrobenzyl, yellow, m. 217°; from p-aminophenylacetic acid, 2-p-aminobenzyl, yellow, m. 213°.

Journal and Proceedings of the Royal Society of New South Wales published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C9H10N2O, Name: (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Beraki, Simret published the artcileA pharmacological screening approach for discovery of neuroprotective compounds in ischemic stroke, Related Products of imidazoles-derivatives, the publication is PLoS One (2013), 8(7), e69233, database is CAplus and MEDLINE.

With the availability and ease of small mol. production and design continuing to improve, robust, high-throughput methods for screening are increasingly necessary to find pharmacol. relevant compounds amongst the masses of potential candidates. Here, we demonstrate that a primary oxygen glucose deprivation assay in primary cortical neurons followed by secondary assays (i.e. post-treatment protocol in organotypic hippocampal slice cultures and cortical neurons) can be used as a robust screen to identify neuroprotective compounds with potential therapeutic efficacy. In our screen about 50% of the compounds in a library of pharmacol. active compounds displayed some degree of neuroprotective activity if tested in a pre-treatment toxicity assay but just a few of these compounds, including Carbenoxolone, remained active when tested in a post-treatment protocol. When further examined, Carbenoxolone also led to a significant reduction in infarction size and neuronal damage in the ischemic penumbra when administered six hours post middle cerebral artery occlusion in rats. Pharmacol. testing of Carbenoxolone-related compounds, acting by inhibition of 11-β-hydroxysteroid dehydrogenase-1 (11β-HSD1), gave rise to similarly potent in vivo neuroprotection. This indicates that the increase of intracellular glucocorticoid levels mediated by 11β-HSD1 may be involved in the mechanism that exacerbates ischemic neuronal cell death and inhibiting this enzyme could have potential therapeutic value for neuroprotective therapies in ischemic stroke and other neurodegenerative disorders associated with neuronal injury.

PLoS One published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C17H20ClN3, Related Products of imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Tang, Sheng published the artcilePerformance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans, Related Products of imidazoles-derivatives, the publication is Journal of Chromatography A (2018), 112-123, database is CAplus and MEDLINE.

Chitosan bis(phenylcarbamate)-(N-cyclohexylformamide)s and chitosan bis(phenylcarbamate)-(N-hexanamide)s were synthesized as chiral selectors for enantiomeric separation Since two types of substituents with different structures were, resp., introduced onto the 2-position and the 3-/6-positions of the glucose skeleton in the chitosans through a heterogeneous modification pathway, the enantioseparation performances of the chiral selectors could be improved. Influence and position of the substituents on chiral recognition and enantioseparation abilities was studied in detail, and the structural dependence on enantioseparation performance was particularly demonstrated. Me- and chloro-substituted chitosan bis(phenylcarbamate)-(N-hexanamide)s possessed comparable enantioseparation performances, whereas chloro-substituted chitosan bis(phenylcarbamate)-(N-cyclohexylformamide)s exhibited much more powerful chiral recognition and enantioseparation abilities than the Me-substituted ones. Among all the prepared chiral selectors, those with the combination of the cyclohexyl group at the 2-position of the glucose skeleton in the chitosan derivatives and the chlorophenyl group at the 3-/6-positions seemed to be more preferable for enantiomeric separation As a result, the chitosan bis(3,4-dichlorophenylcarbamate)-(N-cyclohexylformamide) possessed the best enantioseparation performance. The solvent tolerability of the prepared chiral selectors was also studied. Compared with the classical coated-type chiral separation materials derived from cellulose/amylose derivatives, the N-cyclohexylcarbonyl and N-hexanoyl chitosans based chiral stationary phases possess more favorable solvent tolerability, thus possibly widening their applications for various practical enantioseparations

Journal of Chromatography A published new progress about 161796-78-7. 161796-78-7 belongs to imidazoles-derivatives, auxiliary class Membrane Transporter/Ion Channel,Proton Pump, name is Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide, and the molecular formula is C7H8BBrO3, Related Products of imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Wang, Zhao-Qun published the artcileEnantioseparation characteristics of biselector chiral stationary phases based on derivatives of cellulose and amylose, Related Products of imidazoles-derivatives, the publication is Journal of Chromatography A (2014), 57-68, database is CAplus and MEDLINE.

Cellulose tris(4-methylphenylcarbamate) (CMPC) and cellulose tris(4-chlorophenylcarbamate) (CCPC) are known for their powerful chiral recognition capability, and the chiral columns prepared from these two polymers were commercialized. However, the chiral stationary phases (CSPs) can be only used in the mobile phases containing �0% ethanol (referring to CMPC) or cannot be used in ethanol-containing mobile phases (referring to CCPC). To overcome the defect and to study the enantioseparation characteristics of biselector CSPs, CMPC, cellulose tris(phenylcarbamate) (CPC) and CCPC were, resp., mixed with amylose tris(3,5-dimethylphenylcarbamte) (ADMPC) at a ratio of 1:1 (mol/mol) of glucose unit, and three new CSPs were prepared by coating the resulting blends on 3-aminopropyl silica gel. For the purpose of enantioseparation comparison, the corresponding single selector CSPs were also prepared with the individual derivatives of cellulose and amylose. The enantioseparation evaluation indicated that the biselector CSPs still bear excellent enantioseparation capability. The interaction between two polymers in each blend was studied by using CD spectroscopy. Owing to the interaction, the durability of the biselector CSP derived from CMPC and ADMPC was significantly improved. The CSP could be analyzed with a mobile phase of 100% ethanol. And the biselector CSP derived from CCPC and ADMPC could safely work in a normal phase containing 30% ethanol. Therefore, the workable ranges of the mobile phases were broadened. The elution order on the biselector CSPs was generally dominated by the one on the corresponding single selector CSPs that provided a higher resolution The suprastructure variation caused by the interaction between the individual polymers might also affect the enantioseparation of the biselector CSPs. The trends of the retention factors and the resolutions of partially racemic mixtures are discussed.

Journal of Chromatography A published new progress about 161796-78-7. 161796-78-7 belongs to imidazoles-derivatives, auxiliary class Membrane Transporter/Ion Channel,Proton Pump, name is Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide, and the molecular formula is C6H3ClFNO2, Related Products of imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Ding, Yangyang published the artcileDesign, synthesis, and antitumor activity of novel benzoheterocycle derivatives as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is Journal of Chemical Research (2020), 44(5-6), 286-294, database is CAplus.

The vascular endothelial growth factor receptor-2 signaling pathway promotes the formation of new blood vessels, and vascular endothelial growth factor receptor-2 tyrosine kinase exists in both active and inactive conformations. Novel indole-benzimidazole and indole-benzothiazole derivatives joined by different linkers are designed and synthesized as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase. All the synthesized compounds were evaluated for their cytotoxicity against four human cancer cell lines (HeLa, HT29, A549, and MDA-MB-435) and human umbilical vein endothelial cell. Meanwhile, the inhibitory activities against vascular endothelial growth factor receptor-2 are estimated in vitro and the binding interactions with dual conformations of vascular endothelial growth factor receptor-2 tyrosine kinase are evaluated by mol. docking. Compounds 5a-c and 14 show inhibitory activity against vascular endothelial growth factor receptor-2 tyrosine kinase and promising cytotoxicity, specifically with IC₅₀ values ranging between 0.1 and 1μM, which imply broad-spectrum antitumor activity. These results provide a deep insight into potential structural modifications for developing potent vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors.

Journal of Chemical Research published new progress about 4760-35-4. 4760-35-4 belongs to imidazoles-derivatives, auxiliary class Chloride,Benzimidazole, name is 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, and the molecular formula is C9H9ClN2, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Ding, Yangyang published the artcileDesign, synthesis, and antitumor activity of novel benzoheterocycle derivatives as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase, HPLC of Formula: 7467-35-8, the publication is Journal of Chemical Research (2020), 44(5-6), 286-294, database is CAplus.

The vascular endothelial growth factor receptor-2 signaling pathway promotes the formation of new blood vessels, and vascular endothelial growth factor receptor-2 tyrosine kinase exists in both active and inactive conformations. Novel indole-benzimidazole and indole-benzothiazole derivatives joined by different linkers are designed and synthesized as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase. All the synthesized compounds were evaluated for their cytotoxicity against four human cancer cell lines (HeLa, HT29, A549, and MDA-MB-435) and human umbilical vein endothelial cell. Meanwhile, the inhibitory activities against vascular endothelial growth factor receptor-2 are estimated in vitro and the binding interactions with dual conformations of vascular endothelial growth factor receptor-2 tyrosine kinase are evaluated by mol. docking. Compounds 5a-c and 14 show inhibitory activity against vascular endothelial growth factor receptor-2 tyrosine kinase and promising cytotoxicity, specifically with IC₅₀ values ranging between 0.1 and 1μM, which imply broad-spectrum antitumor activity. These results provide a deep insight into potential structural modifications for developing potent vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors.

Journal of Chemical Research published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C9H10N2O, HPLC of Formula: 7467-35-8.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Yang, Peng-Yu published the artcileChemical Modification and Organelle-Specific Localization of Orlistat-Like Natural-Product-Based Probes, COA of Formula: C18H34N4O5S, the publication is Chemistry – An Asian Journal (2011), 6(10), 2762-2775, database is CAplus and MEDLINE.

Orlistat, also known as tetrahydrolipstatin (THL), is an FDA-approved anti-obesity drug with potential anti-cancer activity. Previously, we developed a chem. proteomic approach, based on the Orlistat-like probe (I) for large-scale identification of unknown cellular targets of Orlistat in human hepatocytes. In this article, we report the chem. synthesis and biol. evaluation of an expanded set of Orlistat-like compounds, with the intention to further dissect and manipulate potential cellular targets of Orlistat. In doing so, we carried out proteome-wide activity-based profiling and large-scale pull-down/LCMS anal. of these compounds in live HepG2 cells, and successfully identified many putative cellular targets for Orlistat and its structural analogs. By qual. assessing the spectra counts of potential protein hits against each of the seventeen Orlistat analogs, we obtained both common and unique targets of these probes. Our results revealed that subtle structural modifications of Orlistat led to noticeable changes in both the cellular potency and target profiles of the drug. In order to further improve the cellular activity of Orlistat, we successfully applied the well-established AGT/SNAP-tag technol. to our cell-permeable, benzylguanine (BG)-containing Orlistat variant (II). We showed that the drug could be delivered and effectively retained in different sub-cellular organelles of living cells. This strategy may provide a general and highly effective chem. tool for the potential sub-cellular targeting of small mol. drugs.

Chemistry – An Asian Journal published new progress about 359860-27-8. 359860-27-8 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Chiral,Amine,Amide,Ether,Inhibitor, name is N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C11H9NO3, COA of Formula: C18H34N4O5S.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem