17450-34-9Relevant academic research and scientific papers
Cell Permeable Imidazole-Desferrioxamine Conjugates: Synthesis and in Vitro Evaluation
Pramanik, Shreya,Chakraborty, Saikat,Sivan, Malavika,Patro, Birija S.,Chatterjee, Sucheta,Goswami, Dibakar
, p. 841 - 852 (2019)
Desferrioxamine (DFO), a clinically approved iron chelator used for iron overload, is unable to chelate labile plasma iron (LPI) because of its limited cell permeability. Herein, alkyl chain modified imidazolium cations with varied hydrophobicities have been conjugated with DFO. The iron binding abilities and the antioxidant properties of the conjugates were found to be similar to DFO. The degree of cellular internalization was much higher in the octyl-imidazolium-DFO conjugate (IV) compared with DFO, and IV was able to chelate LPI in vitro. This opens up a new avenue in using N-alkyl imidazolium salts as a delivery vector for hydrophilic cell-impermeable drugs.
Synergistic cooperation of bi-active hydrogen atoms in protic carboxyl imidazolium ionic liquids to push cycloaddition of CO2 under benign conditions
Wang, Tengfei,Zhu, Xinrui,Mao, Lemin,Liu, Yi,Ren, Tiegang,Wang, Li,Zhang, Jinglai
, (2019)
Nine protic carboxyl imidazolium ionic liquids are synthesized. Then, they are employed to catalyze the chemical fixation of carbon dioxide (CO2) and propylene oxide leading to propylene carbonate in the absence of co-catalyst and organic solvent. HCPImBr presents the best catalytic activity with the product yield of 92% under reaction temperature 120 °C, CO2 initial pressure 1.5 MPa, catalyst amount 0.5 mol%, and reaction time 2.0 h. Even if the reaction temperature and CO2 initial pressure are decreased to 80 °C and 1.0 MPa, respectively, the 85% of product yield would be kept with the 1.0% catalyst dosage along with 12.0 h. With the exception of the most optimal reaction conditions, generality, and recyclability of HCPImBr are also investigated. More importantly, the reaction mechanism is investigated by the density functional theory, which is the first time to report the mechanism for protic carboxyl imidazolium ionic liquids. The catalytic activity of ionic liquids would be further improved with the reasonable combination of cation and anion.
1,3-Bis(2′-hydroxyethyl)imidazolium ionic liquids: Correlating structure and properties with anion hydrogen bonding ability
Deng, Feng,Reeder, Zachary K.,Miller, Kevin M.
, p. 2 - 9 (2014)
A series of 1,3-bis(2′-hydroxyethyl)imidazolium ionic liquids is reported where 1H NMR chemical shift values and thermal stabilities (Td), as determined by thermogravimetric analysis, are correlated with the hydrogen bonding capability of various anions ([Cl-], [Br-], [CF3CO2-], [NO 2-], [MsO-], [NO3-], [TfO-], [BF4-], [NTf2-], and [PF6-]). Use of anions with the strongest hydrogen bonding capability, such as chloride [Cl-], bromide [Br-], and trifluoroacetate [CF3CO2-], led to the furthest observed downfield chemical shift values in DMSO-d6 and the poorest thermal stabilities ([CF3CO2-] -], tetrafluoroborate [BF4-], or bis(trifluoromethylsulfonyl)imide [NTf2-] anion. Optimized structures of selected ionic liquids, as determined by density functional theory calculations at the B3LYP/6-31G + (d,p) level, indicated that the anion preferred to be located above the imidazolium ring and in close proximity to the hydroxyl groups. Calculated dissociation energies (ΔE) and a comparison of key bonding distances (C2 - H, (C2)H···X, O - H, and (O)H···X) also confirmed this structural preference. Copyright
Copper carbenoid mediated N-alkylation of imidazoles and its use in a novel synthesis of bifonazole
Cuevas-Ya?ez, Erick,Serrano, Juan Manuel,Huerta, Gloria,Muchowski, Joseph M.,Cruz-Almanza, Raymundo
, p. 9391 - 9396 (2004)
1H-Imidazoles are readily N-alkylated by a Cu(acac)2 mediated reaction with α-diazocarbonyl compounds or with diazoalkanes generated in situ from the corresponding p-toluensulfonyl hydrazones. The antifungal agent bifonazole was prepared by the latter method. Graphical Abstract.
One-pot preparation method for imidazol-1-yl-acetic acid
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Paragraph 0030-0038, (2020/07/15)
The invention discloses a one-pot preparation method for imidazol-1-yl-acetic acid. The preparation method comprises the following specific steps: 1) dissolving imidazole in a solvent, and then carrying out an N-alkylation reaction on the formed solution and an N-alkylation reagent to obtain methyl imidazol-1-yl-acetate or ethyl imidazol-1-yl-acetate in a reaction intermediate state; and 2) addinghydrous ethanol into a reaction solution obtained in the step 1), continuing heating for a hydrolysis reaction, carrying out cooling for crystallization after the reaction is finished, and carrying out filtering and drying to obtain imidazol-1-yl-acetic acid. According to the method, the starting raw material imidazole is used as an alkali, so the use of a phase transfer catalyst is avoided; theimidazol-1-yl-acetic acid is prepared by the one-pot method, so steps are few, operation is simple, raw material variety is few, post-treatment is simple, reaction yield is high, product purity is high, reaction conditions are mild, cost is low, and safety is good; and the method accords with the trend of green chemical industry and is suitable for industrial production.
Multi-active-center ionic liquid, preparation method and method for catalytically synthesizing cyclic carbonate by using multi-active-center ionic liquid
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Paragraph 0030-0033, (2020/11/23)
The invention relates to a novel multi-active-center ionic liquid, the structural formula of which is shown in the specification, in the formula, n is equal to 1, 2 or 3. The invention also provides amethod for catalytically synthesizing cyclic carbonate by using the ionic liquid. The invention solves the problems of low catalyst performance, harsh reaction conditions and use of an organic solvent or a cocatalyst in the existing method for synthesizing cyclic carbonate by using CO2 and an epoxy compound, and uses a novel multi-active center ionic liquid as a catalyst to catalyze the epoxy compound and CO2 to carry out cycloaddition reaction at the pressure of 0.1-0.5 MPa and the temperature of 30-80 DEG C so as to generate cyclic carbonate. The highest yield can reach 98.5%.
Dihydro quinazolinone derivative, as well as preparation method and application thereof
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Paragraph 0117; 0124; 0125, (2018/07/30)
The invention relates to the technical field of medicines, in particular to a new dihydro quinazolinone derivative with the following chemical structure general formula and pharmaceutically acceptablesalts thereof, (the formula is shown in the description.), A pharmacological experiment shows that the derivative or the salt provided by the invention has higher inhibitory activity on KRAS-PDE delta protein interaction, and has higher anti-tumor activity in vitro. The invention also provides a preparation method of the derivative and the pharmaceutically acceptable salts thereof, and application to preparatioin of a KRAS-PDE delta inhibitor and an anti-tumor drug.
Discovery of Molidustat (BAY 85-3934): A Small-Molecule Oral HIF-Prolyl Hydroxylase (HIF-PH) Inhibitor for the Treatment of Renal Anemia
Beck, Hartmut,Jeske, Mario,Thede, Kai,Stoll, Friederike,Flamme, Ingo,Akbaba, Metin,Ergüden, Jens-Kerim,Karig, Gunter,Keldenich, J?rg,Oehme, Felix,Militzer, Hans-Christian,Hartung, Ingo V.,Thuss, Uwe
, p. 988 - 1003 (2018/04/19)
Small-molecule inhibitors of hypoxia-inducible factor prolyl hydroxylases (HIF-PHs) are currently under clinical development as novel treatment options for chronic kidney disease (CKD) associated anemia. Inhibition of HIF-PH mimics hypoxia and leads to increased erythropoietin (EPO) expression and subsequently increased erythropoiesis. Herein we describe the discovery, synthesis, structure–activity relationship (SAR), and proposed binding mode of novel 2,4-diheteroaryl-1,2-dihydro-3H-pyrazol-3-ones as orally bioavailable HIF-PH inhibitors for the treatment of anemia. High-throughput screening of our corporate compound library identified BAY-908 as a promising hit. The lead optimization program then resulted in the identification of molidustat (BAY 85-3934), a novel small-molecule oral HIF-PH inhibitor. Molidustat is currently being investigated in clinical phase III trials as molidustat sodium for the treatment of anemia in patients with CKD.
Discovery of Novel KRAS-PDEδ Inhibitors by Fragment-Based Drug Design
Chen, Long,Zhuang, Chunlin,Lu, Junjie,Jiang, Yan,Sheng, Chunquan
supporting information, p. 2604 - 2610 (2018/03/26)
Targeting KRAS-PDEδ protein-protein interactions with small molecules represents a promising opportunity for developing novel antitumor agents. However, current KRAS-PDEδ inhibitors are limited by poor cellular antitumor potency and the druggability of the target remains to be validated by new inhibitors. To tackle these challenges, herein, novel, highly potent KRAS-PDEδ inhibitors were identified by fragment-based drug design, providing promising lead compounds or chemical probes for investigating the biological functions and druggability of KRAS-PDEδ interaction.
7-OXO -6-(SULFOOXY)- 1,6-DIAZABICYCLO [3.2.1] OCTANE CONTAINING COMPOUNDS AND THEIR USE IN TREATMENT OF BACTERIAL INFECTIONS
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Page/Page column 51, (2017/06/19)
Compounds of Formula (I) or a stereoisomer or a pharmaceutically acceptable salt thereof, their preparation, and use in treating a bacterial infection are disclosed.
