1666-02-0Relevant articles and documents
Inhibition of Urease, a Ni-Enzyme: The Reactivity of a Key Thiol With Mono- and Di-Substituted Catechols Elucidated by Kinetic, Structural, and Theoretical Studies
Mazzei, Luca,Contaldo, Umberto,Musiani, Francesco,Cianci, Michele,Bagnolini, Greta,Roberti, Marinella,Ciurli, Stefano
, p. 6029 - 6035 (2021)
The inhibition of urease from Sporosarcina pasteurii (SPU) and Canavalia ensiformis (jack bean, JBU) by a class of six aromatic poly-hydroxylated molecules, namely mono- and dimethyl-substituted catechols, was investigated on the basis of the inhibitory efficiency of the catechol scaffold. The aim was to probe the key step of a mechanism proposed for the inhibition of SPU by catechol, namely the sulfanyl radical attack on the aromatic ring, as well as to obtain critical information on the effect of substituents of the catechol aromatic ring on the inhibition efficacy of its derivatives. The crystal structures of all six SPU-inhibitors complexes, determined at high resolution, as well as kinetic data obtained on JBU and theoretical studies of the reaction mechanism using quantum mechanical calculations, revealed the occurrence of an irreversible inactivation of urease by means of a radical-based autocatalytic multistep mechanism, and indicate that, among all tested catechols, the mono-substituted 3-methyl-catechol is the most efficient inhibitor for urease.
Intramolecular hydrogen bonds in normal and sterically compressed o-hydroxy aromatic aldehydes. Isotope effects on chemical shifts and hydrogen bond strength
Hansen, Poul Erik,Kamounah, Fadhil S.,Saeed, Bahjat A.,MacLachlan, Mark J.,Spanget-Larsen, Jens
, (2019)
A number of o-hydroxy aromatic aldehydes have been synthesized to illustrate the effect of steric compression and O···O distances on the intramolecular hydrogen bond and the hydrogen bond energies. Hydrogen bond energies have been calculated using the ‘hb
Two Colour Photoflow Chemistry for Macromolecular Design
Barner-Kowollik, Christopher,Blinco, James P.,De Bruycker, Kevin,Van De Walle, Matthias
, p. 14143 - 14147 (2020)
We report a photochemical flow setup that exploits λ-orthogonal reactions using two different colours of light (λ1=350 nm and λ2=410 nm) in sequential on-line irradiation steps. Critically, both photochemically reactive units (a visi
Direct formylation of fluorine-containing aromatics with dichloromethyl alkyl ethers
Warashina, Takuya,Matsuura, Daisuke,Kimura, Yoshikazu
, p. 587 - 593 (2019/07/22)
Formylations of fluorine-containing aromatic compounds with dichloromethyl alkyl ethers have been investigated. Dichloromethyl propyl ether and dichloromethyl butyl ether have been applied for the formylation of fluorine-containing anisoles to give the corresponding aldehydes in good yields. Application of these ethers is preferable to that of methyl ether, which is prepared from volatile methyl formate. Reaction of fluorine-containing phenols with these dichloromethyl alkyl ethers did not give salicylaldehyde derivatives, leading instead to corresponding aryl formates in high yields. A plausible mechanism is discussed.
Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group
Patel, Jignesh J.,Laars, Marju,Gan, Wei,Board, Johnathan,Kitching, Matthew O.,Snieckus, Victor
supporting information, p. 9425 - 9429 (2018/07/29)
A general synthesis of highly substituted 2-naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with either LiNEt2 or LiNiPr2 into Z-cinnamamides, thus generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation for ring closure to give the aryl 2-naphthols in good to excellent yields. These transformations can be combined to provide a more efficient one-pot process. Mechanistic insight into the remote lateral metalation step, demonstrating the requirement of Z-cinnamamide, is described. Application of this methodology to the synthesis of highly substituted 3,3′-diaryl BINOL ligands is also reported.
Mixture, polymer, optical film, optically anisotropic body, polarizing sheet, display device, antireflective film, and manufacturing method for mixture
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Paragraph 0449-0455, (2019/02/28)
A purpose of the present invention is to provide a means by which a polymer can be efficiently manufactured, said polymer being able to be used in the production of an optical film or similar with good reverse wavelength dispersion. In a mixture according to the present invention, the included amount of a polymerizable compound (I) indicated by formula (I) is greater than 0.2 times the included amount of a polymerizable compound (II) indicated by formula (II). (In the formulas, Ar1 and Ar2 are prescribed ring groups; A1-A4 and B1-B4 are cyclic aliphatic groups or aromatic groups and can have a substituent group; Z1-Z4, Y1-Y4, and L1-L4 are prescribed groups such as -O-, -C(=O)-O-, or -O-C(=O)-; R1-R6 are hydrogen atoms, methyl groups, or chlorine atoms; one of e and f is an integer from 1 to 3 and the other is an integer from 0 to 3; c, d, i, and j are integers from 1 to 20; and a, b, g, and h are 0 or 1).
Formylation of electron-rich aromatic rings mediated by dichloromethyl methyl ether and TiCl4: Scope and limitations
Ramos-Tomillero, Iván,Paradís-Bas, Marta,De Pinho Ribeiro Moreira, Ibério,Bofill, Josep María,Nicolás, Ernesto,Albericio, Fernando
supporting information, p. 5409 - 5422 (2015/05/13)
Here the aromatic formylation mediated by TiCl4 and dichloromethyl methyl ether previously described by our group has been explored for a wide range of aromatic rings, including phenols, methoxy- and methylbenzenes, as an excellent way to produce aromatic aldehydes. Here we determine that the regioselectivity of this process is highly promoted by the coordination between the atoms present in the aromatic moiety and those in the metal core.
A direct and mild formylation method for substituted benzenes utilizing dichloromethyl methyl ether-silver trifluoromethanesulfonate
Ohsawa, Kosuke,Yoshida, Masahito,Doi, Takayuki
, p. 3438 - 3444 (2013/06/26)
A silver trifluoromethanesulfonate (AgOTf)-promoted direct and mild formylation of benzenes has been developed. The reaction utilizing dichloromethyl methyl ether (Cl2CHOMe) and AgOTf powerfully formylated various substituted benzenes under temperature conditions as low as -78 C without losing the protecting groups on the phenolic hydroxyl group.
The novel benzopyran class of selective cyclooxygenase-2 inhibitors. Part III: The three microdose candidates
Wang, Jane L.,Aston, Karl,Limburg, David,Ludwig, Cindy,Hallinan, Ann E.,Koszyk, Francis,Hamper, Bruce,Brown, David,Graneto, Matthew,Talley, John,Maziasz, Timothy,Masferrer, Jaime,Carter, Jeffery
scheme or table, p. 7164 - 7168 (2011/01/03)
In this manuscript, we report the discovery of the substituted 2-trifluoromethyl-2H-benzopyran-3-carboxylic acids as a novel series of potent and selective cyclooxygenase-2 (COX-2) inhibitors. We provide the structure-activity relationships, optimization of design, testing criteria, and human half-life data. The challenge of a surprisingly long half-life (t 1/2 = 360 h) of the first clinical candidate 1 and human t 1/2 had been difficult to predict based on allometric scaling for this class of highly ppb compounds. We used a microdose strategy which led to the discovery of clinical agents 18c-(S), 29b-(S), and 34b-(S) with human half-life of 57, 13, and 11 h.
CANNABINOID RECEPTOR MODULATOR
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Page/Page column 76, (2008/06/13)
A cannabinoid receptor modulator containing a compound represented by Formula (I0) wherein, X is an oxygen atom, etc., R° is an optionally substituted acylamino group, ring A0 is a benzene ring which may further have a substituent in addition to R°, and ring B is an optionally substituted 5-membered heterocycle, or a salt thereof or a prodrug thereof.
