150809-54-4Relevant academic research and scientific papers
Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation
Ma, Xiantao,Xu, Qing,Li, Huan,Su, Chenliang,Yu, Lei,Zhang, Xu,Cao, Hongen,Han, Li-Biao
supporting information, p. 3408 - 3413 (2018/08/06)
The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.
Synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds
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Paragraph 0050; 0051; 0052; 0053, (2017/04/26)
The invention discloses a synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds. According to the synthetic method, alcohols which are cheap, easy to get, wide in source, stable and low in toxicity serve as alkylating reagents, iodine salt which is cheap and easy to get serves as catalysts, no solvent is needed, and the alkyl group phosphorous acid diester compounds can be selectively directly obtained after a reaction. The reaction method is simple, the condition is mild, no organic solvent is needed and operation is simple. According to the method, the requirements for reaction conditions are low, various types of alcohols such as a benzyl group type, an allyl type and a fat type can be utilized as the alkylate reagents to implement the synthesis of different types of substituted alkyl group phosphorous acid diester, and the method can be further expanded to the synthesis of the alkyl group phosphinic acid ester compounds through the reaction between the substituted phosphonous acid diester and the alcohols.
Synthesis and evaluation of stilbene derivatives as a potential imaging agent of amyloid plaques
Hong, Myeng Chan,Kim, Yun Kyung,Choi, Jae Yong,Yang, Si Qiang,Rhee, Hakjune,Ryu, Young Hoon,Choi, Tae Hyun,Cheon, Gi Jeong,An, Gwang Il,Kim, Hye Yun,Kim, Youngsoo,Kim, Dong Jin,Lee, Jun-Seok,Chang, Young-Tae,Lee, Kyo Chul
experimental part, p. 7724 - 7730 (2011/01/13)
Fluorescence probes that can detect Aβ (β-amyloid peptide) plaque are important tools for diagnosis of Alzheimer's disease (AD), and 4-N-methylamino-4′-hydroxystilbene (SB-13) is one of the promising candidate molecules. We report here the synthesis of SB-13 derivatives that consist of various electron donating/withdrawing moieties and distinct size of N-substituents. The synthesized compounds were screened for detection of Aβ40 fibrils in vitro. Four compounds exhibited more than sixfold intensity increase, and they were further analyzed for detail bindings and Aβ plaque imaging. Among these molecules, compound 42 meets two critical requirements for imaging agent; high fluorescence responsiveness and strong binding affinity. This compound showed more than 25-fold increase with the dissociation constant of 1.13 ± 0.37 μM. In AD mouse brain tissue, 42 selectively stained Aβ plaque, more specifically peripheral regions of Aβ plaque. This finding demonstrated its potential use as brain-imaging agents for AD studies.
On the functionalization of [2.2](1,4)phenanthrenoparacyclophane
Hopf, Henning,Hucker, Joachim,Ernst, Ludger
, p. 1891 - 1904 (2008/02/06)
Two routes for preparing functionalized [2.2](1,4) phenanthrenoparacyclophanes are described: either the parent system 2 is subjected to electrophilic substitution (bromination, Friedel-Crafts acylation, Rieche formylation: preparation of 5, 6, 7, 11 and 12) or the desired substituents are incorporated in the early stages of the synthesis by the preparation of the corresponding functionalized styryl paracyclophanes and their photocyclization to the respective phenanthrenocyclophanes. By these specific routes various bronudes (22a,b), ethers (28a-c) and phenols (29a,b) were synthesized. The latter derivatives, on oxidation, furnish para-(31) and ortho-quinonophanes (30, 32, 33), useful substrates for the preparation of cyclophanes containing phenazine subunits (36). The stilbene → phenanthrene photocyclization can also be employed for the preparation of benzothiophenophanes, e.g. 43 and 44, from the respective precursors. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis, antitumor evaluation, and apoptosis-inducing activity of hydroxylated (E)-stilbenes
Lion, Cedric J.,Matthews, Charles S.,Stevens, Malcolm F. G.,Westwell, Andrew D.
, p. 1292 - 1295 (2007/10/03)
The parallel solution-phase synthesis of a series of 30 monohydroxylated (E)-stilbene analogues is described. In vitro screening revealed low micromolar activity (GI50) against the MDA MB 468 breast cancer cell line. Activity in MDA MB 468 cells correlated with the ability to induce apoptosis following drug treatment by the most potent agents in the series, e.g., 5dy and 5jy, an observation further reinforced by Annexin V-FITC analysis and fluorescence microscopy.
Structural effects influencing cis-trans isomerisation in methoxy and cyano substituted stilbene derivatives
Vande Velde, Christophe M. L.,Blockhuys, Frank,Van Alsenoy, Christian,Lenstra, Albert T. H.,Geise, Herman J.
, p. 1345 - 1351 (2007/10/03)
Three substituted stilbenes were synthesised, and their photochemical E-Z isomerisation behaviour in solution studied. A rationalisation of the composition of the equilibrium mixture through the ab initio calculated energy difference between the electroni
