16357-40-7Relevant articles and documents
Titanium mediated reductive amination on solid support: Extending the utility of the 4-hydroxy-thiophenol linker
Breitenbucher, J. Guy,Hui, Hon C.
, p. 8207 - 8210 (1998)
The solid supported synthesis of a library of 8,448 benzopyrans was accomplished using the 4-hydroxythiophenol react and release linker. Reductive aminations were performed in parallel using a Ti(OiPr)4/Na(OAc)3BH reducing system. This reduction was performed without cleavage of resin bound substrates from the nucleophile sensitive linker.
Synergic "click" Boronate/Thiosemicarbazone System for Fast and Irreversible Bioorthogonal Conjugation in Live Cells
Akgun, Burcin,Li, Caishun,Hao, Yubin,Lambkin, Gareth,Derda, Ratmir,Hall, Dennis G.
, p. 14285 - 14291 (2017)
Fast, high-yielding, and selective bioorthogonal "click" reactions employing nontoxic reagents are in high demand for their great utility in the conjugation of biomolecules in live cells. Although a number of click reactions were developed for this purpose, many are associated with drawbacks and limitations that justify the development of alternative systems for both single- or dual-labeling applications. Recent reports have highlighted the potential of boronic ester formation as a bioorthogonal click reaction between abiotic boronic acids and diols. Boronic ester formation is a fast dehydrative process; however it is intrinsically reversible in aqueous medium. We designed and optimized a synergic system based on two bifunctional reagents, a thiosemicarbazide-functionalized nopoldiol and an ortho-acetyl arylboronic acid. Both reagents were shown to be chemically stable and nontoxic to HEK293T cells at concentrations as high as 50 μM. The resulting boronate/thiosemicarbazone adduct is a medium-sized ring that forms rapidly and irreversibly without any catalyst at low μM concentrations, in neutral buffer, with a rate constant of 9 M-1 s-1 as measured by NMR spectroscopy. Control experiments in the presence of competing boronic acids showed no crossover side-products and confirmed the stability and lack of reversibility of the boronate/thiosemicarbazone conjugates. Formation of the conjugates is not affected by the presence of biological diols such as fructose, glucose, and catechol, and the thiosemicarbazide-functionalized nopoldiol is inert to aldehyde electrophiles of the sort found on protein-bound glyoxylyl units. The suitability of this system in the cell-surface labeling of live cells was demonstrated using a SNAP-tag approach to install the boronic acid reagent onto the extracellular domain of the Beta-2 adrenergic receptor in HEK293T cells, followed by incubation with the optimal thiosemicarbazide-functionalized nopoldiol reagent labeled with fluorescein dye. Successful visualization by fluorescence microscopy was possible with a reagent concentration as low as 10 μM, thus confirming the potential of this system in biological applications.
Benzo[d]Isoxazole compound, preparation method and applications thereof
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Paragraph 0161-0163, (2019/01/10)
The invention provides a benzo[d]isoxazole compound, a preparation method and applications thereof, wherein the benzo[d]isoxazole compound has novel structure, can be used as a BET bromodomain receptor inhibitor, and can effectively inhibit the bromodomai
Synthesis of (3-(2-aminopyrimidin-4-yl)-4-hydroxyphenyl)phenyl methanone analogues as inhibitors of vascular endothelial growth factor receptor-2 kinase
More, Kunal N.,Lee, Jinho
, p. 70 - 77 (2017/01/16)
Angiogenesis is critical for tumor growth and mediated mainly by vascular endothelial growth factor (VEGF) signaling. Inhibition of the VEGF signaling pathway has emerged as one of the promising approaches for cancer therapy. VEGF receptor 2 (VEGFR-2) is
