6470-87-7Relevant articles and documents
Novel Family of Gelators of Organic Fluids and the Structure of Their Gels
Lin, Yih-chyuan,Kachar, Bechara,Weiss, Richard G.
, p. 5542 - 5551 (1989)
The macroscopic and microscopic properties of a new family of thermally reversible gelators (ALS) of organic fluids and their gels have been investigated by a variety of techniques.Each ALS contains a 2-substituted anthracenyl-type group coupled directly or indirectly to C3 of a steroidal group.Only weak intermolecular interactions (dipolar and van der Waals forces) need hold the gelator networks in place.In spite of this, a gel of 2percent cholesteryl 4-(2-anthryloxy)butanoate (CAB) in 4-heptanol can be retained in a sealed vessel at room temperature for several months.Experiments with a variety of organic fluids demonstrate that specific gelator-solvent interactions are not necessary for the gels to form.Thus, n-alkanes from heptane to hexadecane afford the same gelation temperature (Tg) with CAB.Molecular shape of fluid is an important factor in Tg since methylcyclohexane is gelled by CAB at a lower temperature than are the n-alkanes, and 4-heptanol is gelled at a higher temperature.The kinetics of gel formation and the Tg have been followed by changes in intensities of absorption, fluorescence, and circular dichroism spectra.The intermolecular packing arrangement among neighboring CAB gelator molecules has been probed by using the above spectral techniques in addition to X-ray diffraction and (1)H NMR studies.They indicate a stacked, helical arrangement for CAB molecules with the anthracenyl groups overlapping partially.Optical and electron microscopies have allowed the gelator structure in CAB/1-octanol and CAB/dodecane gels to be elucidated: they consist of molecular domains (several micrometers in diameter) of fibrous bundles; the fibers have rectangular cross sections of 20.9 nm X 10.4 nm (dodecane gel) and 25.3 nm X 8.2 nm (1-octanol gel).Additionally, the fibers of the CAB/1-octanol gel are helically twisted.These results are compared with information from other gel systems in which the gelator forms intertwined fibers.
Electrochemically driven host-guest interactions on patterned donor/acceptor self-assembled monolayers
Maglione, Maria Serena,Casado-Montenegro, Javier,Fritz, Eva-Corinna,Crivillers, Núria,Ravoo, Bart Jan,Rovira, Concepció,Mas-Torrent, Marta
, p. 3038 - 3041 (2018)
Here, on ITO//Au patterned substrates SAMs of ferrocene (Fc) on the Au regions and of anthraquinone (AQ) on the ITO areas are prepared, exhibiting three stable redox states. Furthermore, by selectively oxidizing or reducing the Fc or AQ units, respectively, the surface properties are locally modified. As a proof-of-concept, such a confinement of the properties is exploited to locally form host-guest complexes with β-cyclodextrin on specific surface regions depending on the applied voltage.
Design, synthesis, and molecular docking studies of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives as xanthine oxidase inhibitors
Zhang, Ting-Jian,Li, Song-Ye,Yuan, Wei-Yan,Zhang, Yi,Meng, Fan-Hao
, p. 893 - 901 (2018/03/21)
A series of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives (1a–j) was designed and synthesized as novel xanthine oxidase inhibitors. Among them, the L/D-phenylalanine derivatives (1d and 1i) and the L/D-tryptophan derivatives (1e and 1j) were effective with micromolar level potency. In particular, the L-phenylalanine derivative 1d (IC50?=?3.0?μm) and the D-phenylalanine derivative 1i (IC50?=?2.9?μm) presented the highest potency and were both more potent than the positive control allopurinol (IC50?=?8.1?μm). Preliminary SAR analysis pointed that an aromatic amino acid fragment, for example, phenylalanine or tryptophan, was essential for the inhibition; the D-amino acid derivative presented equal or greater potency compared to its L-enantiomer; and the 9,10-anthraquinone moiety was welcome for the inhibition. Molecular simulations provided rational binding models for compounds 1d and 1i in the xanthine oxidase active pocket. As a result, compounds 1d and 1i could be promising lead compounds for further investigation.
2 - substituted - 9, 10 - anthraquinone compound, preparation method and use thereof
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Paragraph 0189-0191, (2017/08/15)
The invention belongs to the technical field of medicine, and particularly relates to 2-substituted-9,10-anthraquinone compounds represented by the general formula I, the general formula II, the general formula III and the general formula IV, and pharmaceutically acceptable salts, hydrates or solvates and pharmaceutically acceptable carriers thereof. A preparation method comprises the steps: with phthalic anhydride as a starting material, carrying out a Friedel-Crafts reaction, concentrated sulfuric acid dehydration, NBS bromization and sodium azide substitution, generating a key intermediate 2-azide methyl-9,10-anthraquinone, and finally in the presence of copper sulfate pentahydrate and vitamin C, carrying out a Husigen cycloaddition reaction with substituted alkyne; or carrying out concentrated sulfuric acid dehydration, cyclization, chromium trioxide oxidation and thionyl chloride chlorination, to obtain anthraquinone-2-formyl chloride, then carrying out an acylation reaction with various L-amino acid methyl esters, further hydrolyzing, and thus obtaining the target compounds. The prepared compounds show good results in in-vitro antitumor activity tests.
