5348-07-2Relevant articles and documents
Subsupercritical Water Generated by Inductive Heating Inside Flow Reactors Facilitates the Claisen Rearrangement
Oltmanns, Mona,Kirschning, Andreas
supporting information, p. 1942 - 1946 (2020/11/13)
Claisen rearrangement of electron-deficient O-allylated phenols, including fluorine-modified phenols, is facilitated in aqueous media at high temperatures and pressures under flow conditions, as opposed to organic solvents. The O-allylation of phenols can be coupled with the Claisen rearrangement in an integrated flow system.
Near-Infrared Light-Triggered Chlorine Radical (.Cl) Stress for Cancer Therapy
Bu, Wenbo,Gong, Teng,Jiang, Xingwu,Liu, Yanyan,Meng, Xianfu,Song, Ruixue,Wang, Chao-chao,Wang, Han,Wu, Yelin,Zhai, Shaojie,Zhang, Meng
, p. 21032 - 21040 (2020/09/09)
Free radicals with reactive chemical properties can fight tumors without causing drug resistance. Reactive oxygen species (ROS) has been widely used for cancer treatment, but regrettably, the common O2 and H2O2 deficiency in tumors sets a severe barrier for sufficient ROS production, leading to unsatisfactory anticancer outcomes. Here, we construct a chlorine radical (.Cl) nano-generator with SiO2-coated upconversion nanoparticles (UCNPs) on the inside and Ag0/AgCl hetero-dots on the outside. Upon near-infrared (NIR) light irradiation, the short-wavelength emission UCNP catalyzes .Cl generation from Ag0/AgCl with no dependence on O2/H2O2. .Cl with strong oxidizing capacity and nucleophilicity can attack biomolecules in cancer cells more effectively than ROS. This .Cl stress treatment will no doubt broaden the family of oxidative stress-induced antitumor strategies by using non-oxygen free radicals, which is significant in the development of new anticancer agents.
KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
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Paragraph 00157, (2015/04/15)
Certain compounds, or pharmaceutically acceptable salts or prodrugs thereof, are provided herein. Also provided are pharmaceutical compositions comprising at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein and
KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
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Paragraph 00259, (2013/10/22)
Certain compounds, or pharmaceutically acceptable salts or prodrugs thereof, pharmaceutical compositions comprising the same and methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are de
A general route for the stereoselective synthesis of (E)-(1-propenyl)phenyl esters by catalytic CC bond isomerization
Díaz-álvarez, Alba E.,Crochet, Pascale,Cadierno, Victorio
body text, p. 2611 - 2620 (2012/05/20)
A general and efficient procedure for the stereoselective synthesis of (E)-(1-propenyl)phenyl esters from readily accessible allylphenols has been developed. The process involves a two-step sequence consisting of the initial acylation of the allylphenols with an acid chloride, followed by catalytic CC bond isomerization in the resulting allylphenyl esters. The latter step was performed in methanol at 80 °C using catalytic amounts (0.5 mol %) of the commercially available bis(allyl)-ruthenium(IV) dimer [{RuCl(μ-Cl) (η3:η3-C10H16)} 2] (C10H16=2,7-dimethylocta-2,6-diene-1,8-diyl) . Reactions proceeded in high yields (68-93%) and short times (4-9 h) with complete E-selectivity.
Microwave-accelerated Claisen rearrangement in bicyclic imidazolium [b-3C-im][NTf2] ionic liquid
Lin, Yung-Lun,Cheng, Jen-Yen,Chu, Yen-Ho
, p. 10949 - 10957 (2008/02/13)
With microwaves, a chemically stable ionic liquid [b-3C-im][NTf2] recently developed in our laboratory was used as solvent and successfully applied to accelerate Claisen rearrangement reactions at high temperatures. In the presence of Lewis acid MgCl2, these thermal rearrangements could be achieved in similar reaction times but at lower temperature. For the microwaved reactions studied in this work, without scarifying isolated yields, the reaction times were significantly reduced from hours (by conventional heating) to ≤3 min. Our result also demonstrated that [b-3C-im][NTf2] ionic liquid was a useful solvent substitute and could be recycled multiple times for the studied rearrangement reaction at elevated temperatures.
Accelerating effect of meta substituents in the ester-mediated nucleophilic aromatic substitution reaction
Hattori, Tetsutaro,Takeda, Ayanobu,Suzuki, Kenji,Koike, Nobuyuki,Koshiishi, Eiji,Miyano, Sotaro
, p. 3661 - 3671 (2007/10/03)
The ester-mediated nucleophilic aromatic substitution (SNAr) reaction of 2-methoxybenzoic ester 1 with Grignard reagents 11 is greatly accelerated by introduction of a methoxy or halo substituent at the 3-position of the benzoate ring (7-10). The substituent effects of these groups at the 3-position are compared with those at the 5-position to suggest that the activation mechanism of the methoxy substituent is different from that of the halo substituent; the ligating ability of the 3-methoxy group plays a crucial role in enhancing the reactivity of the 2-methoxy moiety, while the electron-withdrawing ability is more important in the case of the halo groups. It has also been found that introduction of an additional methoxy substituent at the meta-position (33, 34) enables the SNAr methoxy-displacement reaction even at the para-position to the ester activator. The accelerating effect of the 3-bromo substituent is advantageously utilized for regioselective allylation of 3-bromo-2,6-dimethoxybenzoic ester 55 at the 2-position to provide an easy access to a multisubstituted naphthol 59, which is a key compound for the syntheses of michellamines A-C and the related naphthylisoquinoline alkaloids.
Synthesis of methyl 2,3-dihydro-2-benzofurancarboxylates from o-allylphenols via 2-(phenylthiomethyl)-2,3-dihydrobenzofurans
Yodo, Mitsuaki,Harada, Hiroshi
, p. 2361 - 2368 (2007/10/02)
A method for synthesizing methyl 2,3-dihydro-2-benzofurancarboxylates rom o-allylphenols is described.The reaction of 6allyl-2,3-dichlorophenol (3) with benzenesulfenyl chloride (PhSCl) in acetonitrile gave a mixture of PhSCl -adducts, which was heated in aqueous acetonitrile then with sodium bicarbonate to obtain 6,7-dichloro-2-(phenylmethyl)-2,3-dihydrobenzofuran (6). α-Dichlorination of the phenylthiomethyl group of 6 and subsequent methanolysis gave the methyl ester 5 in high yield.The generality of this synthetic method was examined by the conversion of o-allylphenols 11 having various substituents on the benzene ring into the corresponding methyl ester 23.Cyclization of 11 to sulfides 12 could be achived similerly to the case of 3.However, in the subsequent conversions of 12 to 23, selective α-dichlorination followed by methanolysis could be achived only with 12 substituted with an electron-withdrawing group such as a chloro or nitro group.Keywords - oallylphenils; methyl 2,3-dihydro-2-benzofurancarboxylate; 2-(phenylthiomethyl)-2,3-dihydrobenzofuran; benzenesulfenyl chloride; α-chlorination; methanolysis.
α-Adrenoreceptor Reagents. 2. Effects of Modification of the 1,4-Benzodioxan Ring System on α-Adrenoreceptor Activity
Chapleo, Christopher B.,Myers, Peter L.,Butler, Richard C. M.,Davis, John A.,Doxey, John C.,et al.
, p. 570 - 576 (2007/10/02)
Modification of the 1,4-benzodioxan ring present in RX 781094 (1) has not previously been considered.This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives.The dihydroxybenzofuranylimidazoline compound 7 is the only analogue possesing presynaptic antagonist potency and selectivity comparable to that of 1.In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series.Many derivatives, as well as the parent compound 7, were found to possess presynaptic α2-adrenoreceptor antagonist and postsynaptic α1-adrenoreceptor partial agonist properties.Two of the selective presynaptic antagonists,13 and 14, possess greater potency and selectivity than that possessed by 1.The 5-chloro derivative 25 is twice as potent as 1 after oral administration but only about half as potent when given intravenously.
