10269-01-9Relevant articles and documents
Discovery of dually acting small-molecule inhibitors of cancer-resistance relevant receptor tyrosine kinases EGFR and IGF-1R
Hempel, Cornelius,Najjar, Abdulkarim,Totzke, Frank,Sch?chtele, Christoph,Sippl, Wolfgang,Ritter, Christoph,Hilgeroth, Andreas
, p. 2159 - 2166 (2016)
Novel benzo-anellated furo- and pyrrolo[2,3-b]pyridines with a 4-benzylamine substitution have been evaluated as inhibitors of the epidermal growth factor receptor (EGFR). Substituent effects on the determined protein kinase affinity have been discussed based on varied benzylamine residues at the differently substituted molecular scaffolds. Docking studies were carried out in order to explore the potential binding modes of the novel inhibitors. The observed activity data encouraged the measurement of the inhibition of the insulin-like growth factor receptor (IGF-1R), which is known to play an important role in the cancer-resistance development against EGFR inhibitors via receptor heterodimerizations with IGF-1R. We identified novel dual inhibitors of both kinases and report their first cancer cell growth inhibition data.
Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups
Amberchan, Gabriella,Snelling, Rachel A.,Moya, Enrique,Landi, Madison,Lutz, Kyle,Gatihi, Roxanne,Singaram, Bakthan
supporting information, p. 6207 - 6227 (2021/05/06)
The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.
Comparative account of catalytic activity of Ru- and Ni-based nanocomposites towards reductive amination of biomass derived molecules
Bhanage, Bhalchandra M.,Gokhale, Tejas A.,Raut, Amol B.
, (2021/06/18)
This work includes an effective comparison of metallic ruthenium and nickel nanoparticles loaded on montmorillonite clay (MMT) for reductive amination reaction of biomass-derived molecules. It comprises an eco-friendly reaction using water as a solvent, utilizing molecular hydrogen and liquor ammonia (25% aq. solution) for the synthesis of primary amines from bio-derived aldehydes within 3–10 h of reaction time. Various parameters such as temperature, hydrogen pressure, substrate/ammonia concentration ratio, and reaction time were optimized while comparing the selectivity of primary amines for both catalysts. The applicability scope of these catalysts was explored with a library of aryl and heterocyclic aldehydes. The reductive amination of crude furfural extracted from biomass feedstock (rice husk) and pure xylose sugar was tested, showing yields in the range of 11–36%, to show the wider industrial scope of both nanocomposites. Gram scale conversion was also carried out to showcase the bulk scalability of the Ru/MMT catalyst.
Preparation method of (1R)-5-bromo-2,3-dihydro-1-methyl-1H-isoindole
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Paragraph 0044; 0050-0051; 0054-0055; 0058-0059; 0062-0063, (2020/04/17)
The invention discloses a preparation method of (1R)-5-bromo-2,3-dihydro-1-methyl-1H-isoindole. The preparation method comprises the following steps: dissolving 3-bromobenzaldehyde in a first solvent,adding ammonia water and a catalyst, carrying out a reaction in a hydrogen atmosphere, and then performing filtering and concentrating to obtain a first reaction product; dissolving the first reaction product in a second solvent, carrying out cooling to -20 to 20 DEG C, dropwise adding an inorganic acid, adding an aqueous acetaldehyde solution, carrying out heating to a reflux temperature, carrying out a reaction for 5 to 15 h, carrying out reduced-pressure concentration until a volume is 1/3 of an original volume, adjusting a pH value to 9 to 10, conducting stirring overnight, and carrying out suction filtration and recrystallization to obtain a second reaction product; dissolving the second reaction product in a third solvent, dropwise adding a resolving agent, keeping the formed solution at a temperature at 40-80 DEG C for 1-7 hours, performing reduced-pressure concentration until the volume of the solution is reduced by 1/2, conducting stirring overnight at room temperature, and performing suction filtration and washing; and adding the obtained solid into water, slightly heating the solid to dissolve the solid, adjusting a pH value to 9-10, cooling the formed solution to 10 DEG C, carrying out stirring overnight, and performing suction filtration to obtain a target product. The preparation method has the advantages of simple operation, usage of easily available raw materials, reduced cost and applicability to industrial production.
