14548-39-1Relevant articles and documents
Light-Modulated Self-Blockage of a Urea Binding Site in a Stiff-Stilbene Based Anion Receptor
de Jong, Jorn,Feringa, Ben L.,Wezenberg, Sander J.
, p. 3306 - 3310 (2019)
Anion binding to a receptor based on stiff-stilbene, which is equipped with a urea hydrogen bond donating group and a phosphate or phosphinate hydrogen bond accepting group, can be controlled by light. In one photoaddressable state (E isomer) the urea binding site is available for binding, while in the other (Z isomer) it is blocked because of an intramolecular interaction with its hydrogen bond accepting motif. This intramolecular interaction is supported by DFT calculations and 1H NMR titrations reveal a significantly lower anion binding strength for the state in which anion binding is blocked. Furthermore, the molecular switching process has been studied in detail by UV/Vis and NMR spectroscopy. The presented approach opens up new opportunities toward the development of photoresponsive anion receptors.
Synthesis and antitumor activity of aza-brazilan derivatives containing imidazolium salt pharmacophores
Huang, Mingqin,Duan, Shengzu,Ma, Xueqiong,Cai, Bicheng,Wu, Dongmei,Li, Yan,Li, Liang,Zhang, Hongbin,Yang, Xiaodong
supporting information, p. 1027 - 1036 (2019/06/27)
The synthesis of a series of novel aza-brazilan derivatives containing imidazolium salt pharmacophores is presented. The biological activity of such imidazolium salts was further evaluated in vitro against a panel of human tumor cell lines. The results suggest that the electron-withdrawing group on the aza-brazilan moiety, substituted 5,6-dimethyl-benzimidazole ring and substitution of the imidazolyl-3-position with a 4-methylbenzyl group were essential for modulating the cytotoxic activity. Compounds 55 and 39, bearing a 4-methylbenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, were found to be the most potent compounds with IC50 values of 0.52-1.30 μM and 0.56-1.51 μM against four human tumor cell lines investigated. Particularly, compound 57 exhibited inhibitory activity against the MCF-7 cell line with an IC50 value of 0.35 μM and was 56-fold more sensitive than DDP. Moreover, compound 55 inhibited cell proliferation through inducing G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.
LIQUID CRYSTAL COMPOUND, LIQUID CRYSTAL COMPOSITION, AND LIQUID CRYSTAL DISPLAY DEVICE
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Paragraph 0057, (2016/10/07)
PROBLEM TO BE SOLVED: To provide a liquid crystal compound, a liquid crystal composition, and a liquid crystal device using the compound or the composition. SOLUTION: The liquid crystal compound is represented by formula (I). In formula (I), R1 represents H, an alkyl having 1 to 10 carbon atoms, or the like; R2 represents an alkenyl having 2 to 10 carbon atoms or a fluoroalkenyl having 2 to 10 carbon atoms and one or two non-adjacent -CH2- in R2 is replaced by -O- or an ether having 2 to 10 carbon atoms; A1 to A4 each independently represent a formula below, where R3 independently represents H or a halogen; Z1 to Z3 each independently represents a sing bond, -CH2-, -CH2O-, -OCH2-, -CF=CF-, -COO-, -OCO-, -CF2O-, -OCF2-, -C≡C-, -CH=CH-, or the like; and n and m each independently represent 0 or 1. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
Recyclable Hypervalent-Iodine-Mediated Dehydrogenative α,β′-Bifunctionalization of β-Keto Esters under Metal-Free Conditions
Duan, Ya-Nan,Cui, Li-Qian,Zuo, Lin-Hong,Zhang, Chi
supporting information, p. 13052 - 13057 (2015/09/07)
We have developed a method for recyclable hypervalent-iodine-mediated direct dehydrogenative α,β′- bifunctionalization of β-ketoesters and β-diketones under metal-free conditions, which affords a straightforward way to synthesize benzo-fused 2,3-dihydrofurans. This efficient, mild method, which has a wide substrate scope and good functional-group tolerance, was used for the multistep synthesis of the protected aglycone of a naturally occurring phenolic glycoside. A mechanism involving Michael addition to an enone intermediate and subsequent oxidative cyclization is proposed.
Non-conventional methodologies in the synthesis of 1-indanones
Oliverio, Manuela,Nardi, Monica,Costanzo, Paola,Cariati, Luca,Cravotto, Giancarlo,Giofre, Salvatore Vincenzo,Procopio, Antonio
, p. 5599 - 5610 (2014/06/10)
1-Indanones have been successfully prepared by means of three different non-conventional techniques, namely microwaves, high-intensity ultrasound and a Q-tube reactor. A library of differently substituted 1-indanones has been prepared via one-pot intramolecular Friedel-Crafts acylation and their efficiency and "greenness" have been compared.
Synthesis of 1,3-diketones from 3-(4-R-phenyl)propionic acids
Kim,Shokova,Tafeenko,Kovalev
, p. 464 - 468 (2014/06/10)
Self-acylation of 3-(4-R-phenyl)propionic acids (R = H, Br, 1-adamantyl) in trifluoroacetic anhydride catalyzed by trifluoromethanesulfonic acid provides a simple and efficient synthesis of 1,3-diketones. Indan-1-ones formed in the first step undergo acylation to give the corresponding 2-(3-phenyl-1-oxopropyl) indan-1-ones as the major products. One-pot synthesis of polysubstituted pyrazoles directly from 3-(4-R-phenyl)propionic acids is described.
(CF3CO)2O/CF3so3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
Kim, JungKeun,Shokova, Elvira,Tafeenko, Victor,Kovalev, Vladimir
, p. 2270 - 2278 (2014/12/11)
A very simple and convenient reaction for 1,3-diketone preparation from carboxylic acids and aromatic ketones in TFAA/TfOH system is described. When the β-phenylpropionic acids were used as starting materials, they initially gave 1-indanones and then underwent further acylation with the formation of 2-(β-phenylpropionyl)-1-indanones as the main reaction products. In addition, the application of the proposed protocol allowed for the synthesis of selected polysubstituted pyrazoles in a one-pot procedure directly from acids and ketones.
Catalytic asymmetric cross-dehydrogenative coupling: Activation of C-H bonds by a cooperative bimetallic catalyst system
Cao, Weidi,Liu, Xiaohua,Peng, Ruixue,He, Peng,Lin, Lili,Feng, Xiaoming
supporting information, p. 3470 - 3472 (2013/05/23)
A cooperative bimetallic catalyst system was applied in the catalytic asymmetric cross-dehydrogenative coupling of β-ketoesters and xanthene. Various optically active xanthene derivatives bearing a quaternary stereogenic carbon center were obtained in moderate to good yields (up to 90%) with excellent enantioselectivities (up to 99% ee). Meanwhile, a transition-state model was proposed to explain the origin of the asymmetric induction.
AROMATIC KETONE SYNTHESIS WITH AMIDE REAGENTS AND RELATED REACTIONS
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Paragraph 0038-0039, (2013/10/22)
A method of preparing an aryl carbonyl or aryl thiocarbonyl compound, comprises reacting an N-(nitroaryl)-amide or N-(nitroaryl)-thioamide with an aromatic ring, with a superacid catalyst, to produce the aryl carbonyl or aryl thiocarbonyl compound. The superacid is present in an amount of at most 8 equivalents in proportion to the N-(nitroaryl)-amide or N-(nitroaryl)-thioamide. A method of preparing aryl amide or aryl thioamide, comprises reacting an N-(nitroaryl)-carbamide or N-(nitroaryl)-thiocarbamide with an aromatic ring, with a superacid catalyst, to produce the aryl amide or aryl thioamide.
Friedel-crafts acylation with amides
Raja, Erum K.,Deschepper, Daniel J.,Nilsson Lill, Sten O.,Klumpp, Douglas A.
experimental part, p. 5788 - 5793 (2012/07/30)
Friedel-Crafts acylation has been known since the 1870s, and it is an important organic synthetic reaction leading to aromatic ketone products. Friedel-Crafts acylation is usually performed with carboxylic acid chlorides or anhydrides, while amides are generally not useful substrates in these reactions. Despite being the least reactive carboxylic acid derivative, we have found a series of amides capable of providing aromatic ketones in good yields (55-96%, 17 examples). We propose a mechanism involving diminished C-N resonance through superelectrophilic activation and subsequent cleavage to acyl cations.
