104-63-2Relevant academic research and scientific papers
A One-pot Synthesis of Nitrohydroxylated Pyrrolidine and Piperidine Ring Sytems by Tandem Michael-Henry Reaction
Barco, Achille,Benetti, Simonetta,Risi, Carmela De,Pollini, Gian P.,Romagnoli, Romeo,Zanirato, Vinicio
, p. 9293 - 9296 (1994)
Nitrohydroxylated pyrrolidine and piperidine ring systems are coveniently obtained through a one-pot procedure involving sequential Michael-Henry reaction between nitroethylene and a nitrogen nucleophile incorporating a suitably placed precursor for the generation either reductively or oxidatively of an aldehyde group which is directly trapped in the subsequent nitroaldolization step.
Discovery of benzimidazole analogs as a novel interleukin-5 inhibitors
Boggu, Pulla Reddy,Kim, Youngsoo,Jung, Sang-Hun
, (2019)
A series of novel hydroxyethylaminomethylbenzimidazole analogs 5a-y were synthesized and evaluated for their IL-5 inhibitory activity using pro-B Y16 cell line. Among them, 2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino)butan-1-ol (5e, 94.3% inhibition at 30 μM, IC50 = 3.5 μM, cLogP = 4.132) and 3-cyclohexyl-2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino) propan-1-ol (5k, 94.7% inhibition at 30 μM, IC50 = 5.0 μM, cLogP = 6.253) showed the most potent inhibitory activity. The essential feature of SAR (Fig. 5) indicated that the chromenone ring can be replaced by a benzimidazole ring to maintain the inhibitory activity. In addition, the hydroxyethylaminomethyl group was suitable for the IL-5 inhibitory activity. Moreover, the hydrophobic substituents on carbon play an important role in the IL-5 inhibitory activity of these analogs. However, N-substituted analogs did not improve inhibitory activity. In addition, MTT assay of 5e and 5k with normal B lymphoblasts revealed that they had no significant effects on cell viability.
Synthesis of β-amino alcohols from aromatic amines and alkylene carbonates using Na-Y zeolite catalyst
Shivarkar, Anandkumar B.,Gupte, Sunil P.,Chaudhari, Raghunath V.
, p. 1374 - 1378 (2006)
A simple, efficient, and environmentally benign methodology for the synthesis of β-amino alcohols from aromatic amines and alkylene carbonates in the presence of the highly active and reusable solid base catalyst Na-Y zeolite is demonstrated. Georg Thieme Verlag Stuttgart.
AgI/TMG-Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2-Aminoethanols to 2-Oxazolidinones
Li, Xue-Dong,Song, Qing-Wen,Lang, Xian-Dong,Chang, Yao,He, Liang-Nian
, p. 3182 - 3188 (2017)
Chemical valorization of CO2 to access various value-added compounds has been a long-term and challenging objective from the viewpoint of sustainable chemistry. Herein, a one-pot three-component reaction of terminal propargyl alcohols, CO2, and 2-aminoethanols was developed for the synthesis of 2-oxazolidinones and an equal amount of α-hydroxyl ketones promoted by Ag2O/TMG (1,1,3,3-tetramethylguanidine) with a TON (turnover number) of up to 1260. By addition of terminal propargyl alcohol, the thermodynamic disadvantage of the conventional 2-aminoethanol/CO2 coupling was ameliorated. Mechanistic investigations including control experiments, DFT calculation, kinetic and NMR studies suggest that the reaction proceeds through a cascade pathway and TMG could activate propargyl alcohol and 2-aminoethanol through the formation of hydrogen bonds and also activate CO2.
Charge neutral rhenium tricarbonyl complexes of tridentate N-heterocyclic carbene ligands that bind to amyloid plaques of Alzheimer's disease
Barnard, Peter J.,Donnelly, Paul S.,McLean, Catriona A.,Noor, Asif,Wiratpruk, Nuchareenat
, p. 4559 - 4569 (2020)
Two tridentate ligand systems bearing N-heterocyclic carbene (NHC), amine and carboxylate donor groups coupled to benzothiazole- or stilbene-based amyloid binding moieties were synthesised. Reaction of the imidazolium salt containing pro-ligands with Re(CO)5Cl yielded the corresponding rhenium metal complexes which were characterised by NMR, and X-ray crystallography. These ligands are of interest for the potential preparation of technetium-99m imaging agents for Alzheimer's disease and the capacity of these rhenium complexes bind to amyloid fibrils composed of amyloid-β peptide and amyloid plaques in human frontal cortex brain tissue was evaluated using fluorescence microscopy. These studies show that the complexes bound efficiently to amyloid-β fibrils and some evidence of binding to amyloid-β plaques.
Convenient methods for the hydrolysis of oxazolidinones to vicinal aminoalcohols
Katz, Steven J,Bergmeier, Stephen C
, p. 557 - 559 (2002)
We have developed two convenient methods for hydrolysis of 2-oxazolidinones to the corresponding vicinal aminoalcohols. N-Substituted oxazolidinones can be readily hydrolyzed using Dowex 1×8-100 resin. N-Unsubstituted oxazolidinones cannot be hydrolyzed using Dowex resins but are effectively hydrolyzed using polymer supported ethylenediamine.
Introduction of the 4,4,4-Trifluorobut-2-ene Chain Exploiting a Regioselective Tsuji-Trost Reaction Catalyzed by Palladium Nanoparticles
Hemelaere, Rémy,Desroches, Justine,Paquin, Jean-Fran?ois
, p. 1770 - 1773 (2015)
A palladium-nanoparticle-catalyzed Tsuji-Trost reaction of 4,4,4-trifluorobut-2-en-1-yl acetate and ethyl(4,4,4-trifluorobut-2-en-1-yl)carbonate was accomplished with various nucleophiles including phenols, amines, and malonates. In the case of the phenols, isomerization of the double bond in the product (up to 20%) was observed as a side reaction. Further synthetic transformations including hydrogenation, the Diels-Alder reaction, and asymmetric dihydroxylation of a product were also examined.
Ionic liquid-promoted three-component domino reaction of propargyl alcohols, carbon dioxide and 2-aminoethanols: A thermodynamically favorable synthesis of 2-oxazolidinones
Xia, Shumei,Song, Yu,Li, Xuedong,Li, Hongru,He, Liang-Nian
, (2018)
To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2 and realize incorporation CO2 under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of α-hydroxyl ketones. The ionic liquid structure, reaction temperature and reaction time were in detail investigated. And 15 mol% 1,5,7-triazabicylo[4.4.0]dec-5-ene ([TBDH][TFE]) trifluoroethanol was found to be able to synergistically activate the substrate and CO2, thus catalyzing this cascade reaction under atmospheric CO2 pressure. By employing this task-specific ionic liquid as sustainable catalyst, 2-aminoethanols with different substituents were successfully transformed to 2-oxazolidinones with moderate to excellent yield after 12 h at 80 °C.
Selective O-benzylation of aminoalkanols
Hu,Cassady
, p. 907 - 913 (1995)
A simple and one-step method has been developed for selective O-benzylation of aminoalkanols. Study of steric effects shows the best selectivity in adjacent 1°-OH vs 2°-CHNH2 and decreased selectivity in 2°-OH vs 1°-CH2NH2 and non adjacent aminoalkanol.
Optimization of gefitinib analogues with potent anticancer activity
Yin, Kai-Hao,Hsieh, Yi-Han,Sulake, Rohidas S.,Wang, Su-Pei,Chao, Jui-I.,Chen, Chinpiao
, p. 5247 - 5250 (2014)
The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant anti-cancer activities against human cancer cell lines. In particular, compounds 52-54 showed excellent potency against cancer cells. Convergent synthetic approach has been developed for the synthesis of gefitinib intermediate which can lead to gefitinib as well as numerous analogues.
