- CHEMICAL COMPOUNDS
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Compounds that are useful as modulators of transmembrane protein 173 (TMEM173), also known as STING (Stimulator of Interferon Genes), and methods for treating Hepatitis B virus-related conditions in mammals by administering such a compound, are disclosed.
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Paragraph 00194-00196
(2020/10/20)
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- PIII/PV=O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles
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An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C?N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones.
- Li, Gen,Luzung, Michael R.,Nykaza, Trevor V.,Radosevich, Alexander T.,Yang, Junyu
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supporting information
p. 4505 - 4510
(2020/02/05)
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- CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines
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CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently
- Sheng, Wei-Jian,Ye, Qing,Yu, Wu-Bin,Liu, Ren-Rong,Xu, Meng,Gao, Jian-Rong,Jia, Yi-Xia
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supporting information
p. 599 - 601
(2015/02/19)
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- Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride
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An efficient and one-pot synthetic method for the regioselective ortho-nitration of the N-phenyl carboxamides and primary anilines has been developed by using bismuth nitrate and acetic anhydride as the nitrating reagents. Reaction proceeds at room temperature and results in corresponding ortho-nitrated products in moderate to excellent yields. This method provides an operationally simple, regioselective, and efficient access to synthesize o-nitro anilines under the mild conditions.
- Lu, Yang,Li, Yaming,Zhang, Rong,Jin, Kun,Duan, Chunying
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supporting information
p. 9422 - 9427
(2013/10/08)
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- Trifluoroacetylation of amines with trifluoroacetic acid in the presence of trichloroacetonitrile and triphenylphosphine
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We developed a mild and convenient trifluoroacetylation process for amines using a combination of trichloroacetonitrile and triphenylphosphine. The reaction that we designed is applicable to the trifluoroacetylation of a wide variety of amines, including amines with stereogenic centers, which underwent trifluoroacetylation without racemization.
- Kim, Joong-Gon,Jang, Doo Ok
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scheme or table
p. 683 - 685
(2010/04/02)
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- A one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid as a trifluoroacetylating reagent
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A convenient procedure for the preparation of aryl trifluoroacetamides from aryl amines is described that employs 2-4 M equiv of trifluoroacetic acid in refluxing xylene as a trifluoroacetylating agent. Addition of an amount of pyridine that is equimolar to the amount of trifluoroacetic acid present in the reaction mixture facilitates the trifluoroacetylation of rather basic arylamines.
- Ohtaka, Junpei,Sakamoto, Takeshi,Kikugawa, Yasuo
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experimental part
p. 1681 - 1683
(2009/09/05)
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- On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases
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Cholinesterases, in addition to their well-known esterase action, also show an aryl acylamidase (AAA) activity whereby they catalyze the hydrolysis of amides of certain aromatic amines. The biological function of this catalysis is not known. Furthermore, it is not known whether the esterase catalytic site is involved in the AAA activity of cholinesterases. It has been speculated that the AAA activity, especially that of butyrylcholinesterase (BuChE), may be important in the development of the nervous system and in pathological processes such as formation of neuritic plaques in Alzheimer's disease (AD). The substrate generally used to study the AAA activity of cholinesterases is N-(2-nitrophenyl)acetamide. However, use of this substrate requires high concentrations of enzyme and substrate, and prolonged periods of incubation at elevated temperature. As a consequence, difficulties in performing kinetic analysis of AAA activity associated with cholinesterases have hampered understanding this activity. Because of its potential biological importance, we sought to develop a more efficient and specific substrate for use in studying the AAA activity associated with BuChE, and for exploring the catalytic site for this hydrolysis. Here, we describe the structure-activity relationships for hydrolysis of anilides by cholinesterases. These studies led to a substrate, N-(2-nitrophenyl)trifluoroacetamide, that was hydrolyzed several orders of magnitude faster than N-(2-nitrophenyl)acetamide by cholinesterases. Also, larger N-(2-nitrophenyl)alkylamides were found to be more rapidly hydrolyzed by BuChE than N-(2-nitrophenyl)acetamide and, in addition, were more specific for hydrolysis by BuChE. Thus, N-(2-nitrophenyl)alkylamides with six to eight carbon atoms in the acyl group represent suitable specific substrates to investigate further the function of the AAA activity of BuChE. Based on the substrate structure-activity relationships and kinetic studies, the hydrolysis of anilides and esters of choline appears to utilize the same catalytic site in BuChE.
- Darvesh, Sultan,McDonald, Robert S.,Darvesh, Katherine V.,Mataija, Diane,Mothana, Sam,Cook, Holly,Carneiro, Karina M.,Richard, Nicole,Walsh, Ryan,Martin, Earl
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p. 4586 - 4599
(2007/10/03)
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- HUMAN CHYMASE INHIBITORS
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The present invention provides a benzimidazole derivative or its pharmaceutically permissible salt expressed by the following formula (1). Further, the present invention provides a human chymase activity inhibitor containing the substance as an active ingredient. (the ring marked with A expresses a pyridine ring or a benzene ring; X1 and X2 are each a hydrogen atom, a halogen atom, a trihalomethyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or the like; B is a substituted or unsubstituted alkylene group, or the like; E is -COOR4 or the like; G is a substituted or unsubstituted alkylene group; J is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and M is a sulfur atom, sulfoxide, sulfone or the like).
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- A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles
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Methyl cis-deisopropyldehydroabietate was selectively nitrated at the 12-position by reaction with 'claycop', a montmorillonite clay impregnated with copper(II) nitrate. The 12-nitro compound was reduced to the corresponding amine and this was subjected to a combined acylation and ortho nitration. The compounds so produced were further converted into octahydro-1H-phenanthro[2,3-d]imidazoles by reductive cyclization. The same acylation-ortho nitration methodology was shown to provide a short synthesis of 2-substituted benzimidazoles from aniline.
- Fonseca, Tatiana,Gigante, Bárbara,Gilchrist, Thomas L
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p. 1793 - 1799
(2007/10/03)
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- Ozone-mediated Reaction of Anilides and Phenyl Esters with Nitrogen Dioxide: Enhanced Ortho-reactivity and Mechanistic Implications
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In the presence of ozone, anilides 1 can be nitrated rapidly with nitrogen dioxide in chloroform at 0 deg C to give a high proportion of ortho-nitro derivatives (ortho:para = 1.2-4.4) in good yields.The phenyl esters 15 can be similarly nitrated on the aromatic ring without significant cleavage of the ester bond, giving a mixture of isomeric nitro derivatives in which the ortho-isomer predominantes (ortho:para = 1.1-1.5).The oridin of the enhanced ortho reactivity is discussed in terms of an electron-transfer process involving the nitrogen trioxide as initial electrophile.
- Suzuki, Hitomi,Tatsumi, Atsuo,Ishibashi, Taro,Mori, Tadashi
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p. 339 - 344
(2007/10/02)
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- Nitrations and Oxidations with Inorganic Nitrate Salts in Trifluoroacetic Anhydride
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Metal nitrates in trifluoroacetic anhydride nitrate many aromatic compounds in high yields at room temperature, including polymers with aromatic groups.However, this system oxidizes phenols to quinoid products.
- Crivello, J.V.
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p. 3056 - 3060
(2007/10/02)
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