- Formation of potentially prebiotic amphiphiles by reaction of β-hydroxy-n-alkylamines with cyclotriphosphate
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(Chemical Equation Presented) The long and the short of it: In water, long-chain β-hydroxy-n-alkylamines are converted to their O-monophosphates by reaction with cyclotriphosphate. With short-chain pVhydroxy-n-alkylamines, N-triphosphates are formed instead. The difference results from the formation of surfactant assemblies from the long-chain compounds. This surfactant control of reactivity may be of relevance to the prebiotic formation of amphiphiles. P: phosphate unit.
- Mullen, Lee B.,Sutherland, John D.
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Read Online
- INHIBITORS OF KEAP1-Nrf2 PROTEIN-PROTEIN INTERACTION
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Sultam compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with the KEAP1-Nrf2 interaction, such as inflammatory bowel disease, including Crohn's disease and ulcerative colitis.
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Paragraph 1918-1919
(2020/03/01)
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- HYDROXYPYRIDOXAZEPINES AS NRF2 ACTIVATORS
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The present invention relates hydroxypyridoxazepine compounds, methods of making them, pharmaceutical compositions containing them and their use as Nrf2 activators. In particular, the invention relates to compounds of Formula (I), and pharmaceutically acc
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Page/Page column 94
(2020/08/28)
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- Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
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A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.
- Yang, Hui,Zheng, Wen-Hua
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supporting information
p. 16177 - 16180
(2019/11/03)
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- BISARYL AMIDES AS NRF2 REGULATORS
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The present invention relates to bisaryl amide analogs, pharmaceutical compositions containing them and their use as NRF2 activators. In particular, the invention relates to bisaryl heterocycles of Formula (I).
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Page/Page column 127
(2018/09/11)
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- BISARYL HETEROCYCLES AS NRF2 ACTI
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The present invention relates to bisaryl heterocycle compounds, methods of making them, pharmaceutical compositions containing them and their use as NRF2 activators. In particular, the invention relates to bisaryl heterocycles of Formula (I),
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Page/Page column 104; 105
(2018/07/05)
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- NRF2 COMPOUNDS
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The present invention relates to a compound which is (R)-3-(1,4- dimethyl-1 H-benzo[d][1,2,3]triazol-5-yl)-3-(3-(((R)-2-ethyl-2,3- dihydropyrido[2,3-f][l,4]oxazepin-4(5H)-yl)methyl)-4-methylphenyl) propanoic acid (I), or a pharmaceutically acceptable salt
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Page/Page column 19; 42
(2018/07/05)
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- ETHER LINKED TRIAZOLES AS NRF2 REGULATORS
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The present invention relates to ether-linked triazole compounds, methods of making them, pharmaceutical compositions containing them and their use as NRF2 activators. In particular, the invention relates to compounds of Formula (I), and pharmaceutically acceptable salts thereof:
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Page/Page column 86
(2018/07/05)
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- The hydrolysis of epoxides catalyzed by inorganic ammonium salts in water: Kinetic evidence for hydrogen bond catalysis
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Naturally-occurring inorganic ammonium ions have been recently reported as efficient catalysts for some organic reactions in water, which contributes to the understanding of the chemistry in some natural environments (soils, seawater, atmospheric aerosols, .) and biological systems, and is also potentially interesting for green chemistry as many of their salts are cheap and non-toxic. In this work, the effect of NH4+ ions on the hydrolysis of small epoxides in water was studied kinetically. The presence of NH4+ increased the hydrolysis rate by a factor of 6 to 25 compared to pure water and these catalytic effects were shown not to result from other ions, counter-ions or from acid or base catalysis, general or specific. The small amounts of amino alcohols produced in the reactions were identified as the actual catalysts by obtaining a strong acceleration of the reactions when adding these compounds directly to the epoxides in water. Replacing the amino alcohols by other strong hydrogen-bond donors, such as trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) gave the same results, demonstrating that the kinetics of these reactions was driven by hydrogen-bond catalysis. Because of the presence of many hydrogen-bond donors in natural environments (for instance amines and hydroxy-containing compounds), hydrogen-bond catalysis is likely to contribute to many reaction rates in these environments.
- Nozière,Fache,Maxut,Fenet,Baudouin,Fine,Ferronato
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p. 1583 - 1590
(2018/02/06)
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- BIARYL PYRAZOLES AS NRF2 REGULATORS
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The present invention relates to biaryl pyrazole compounds, methods of making them, pharmaceutical compositions containing them and their use as NRF2 regulators.
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Page/Page column 139
(2017/08/01)
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- Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
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This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.
- Lee, Melissa,Sanford, Melanie S.
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supporting information
p. 572 - 575
(2017/02/10)
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- NRF2 REGULATORS
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Provided are aryl analogs,pharmaceutical compositions containing them and their use as NRF2 regulators.
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Page/Page column 202
(2017/01/02)
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- NRF2 REGULATORS
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The present invention relates to bis aryl analogs, pharmaceutical compositions containing them and their use as Nrf2 regulators.
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Page/Page column 126; 349
(2015/07/07)
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- α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
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N-Phosphonate terminal aziridines undergo lithium 2,2,6,6- tetramethylpiperidide-induced N-to C-[1,2]-anionic phosphonyl group migration under experimentally straightforward conditions, to provide a stereocontrolled access to synthetically valuable trans-
- Hodgson, DaviD. M.,Xu, Zhaoqing
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supporting information; experimental part
p. 978 - 983
(2011/03/22)
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- Facile one-pot method for the synthesis of novel N-dichloroacetyl-1,3- oxazolidines
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A short and efficient route to synthesis and structural characterization of a series of novel N-dichloroacetyl-5-ethyl-1,3-oxazolidine derivatives has been developed. These new compounds, characterized by the substitution at position 2 by alkyls, cycloalkanes, benzyls, or aryls, have been synthesized in good yields via a sequential procedure involving cycloaddition, condensation, and acylation. All the compounds are characterized by infrared, 1H NMR, and 13C NMR.
- Fu, Ying,Fu, Honggang,Ye, Fei,Mao, Jingdong,Wen, Xiaotian
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scheme or table
p. 2454 - 2463
(2009/12/06)
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- Amine-directed hydroboration: Scope and limitations
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Iodine activation induces intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes with good to excellent control of regiochemistry compared to control experiments using excess THF?BH3. Deuterium labeling and other evidence confirm that the iodine-induced hydroboration reaction of homoallylic amine boranes occurs via an intramolecular mechanism equivalent to the classical 4-center process and without competing retro-hydroboration. Longer carbon chain tethers result in lower regioselectivity, whereas the shorter tether in allylic amines results in a switch to dominant intermolecular hydroboration. Regioselectivity in THF?BH3 control experiments is higher for the allylic amine boranes compared to the iodine activation experiments, whereas the reverse is true for homoallylic amine borane activation.
- Scheideman, Matthew,Wang, Guoqiang,Vedejs, Edwin
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supporting information; experimental part
p. 8669 - 8676
(2009/02/03)
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- Lithiation-induced migrations from nitrogen to carbon in terminal aziridines
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(Chemical Equation Presented) Benefiting from deprotection: Lithium 2,2,6,6-tetramethylpiperidide induces N-Boc or N-phosphonate terminal aziridines to undergo regio- and stereoselective N-to-C migration of the protecting group, giving synthetically valua
- Hodgson, David M.,Humphreys, Philip G.,Xu, Zhaoqing,Ward, John G.
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p. 2245 - 2248
(2008/02/14)
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- Process for the selective enzymatic hydroxylation of aldehydes and ketones
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A process for the selective enzymatic hydroxylation of aldehydes and ketones using chiral anchor-protective groups.
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- Cytokine potentiator and pharmaceutical formulation for cytokine administration
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A cytokine activity enhancer comprising an ethanolamine derivative of the following general formula (I) or a salt thereof, or comprising it along with cytokine or a cytokine production promoter; and also a medicine for diseases with lowered cytokine activity, comprising, as the active ingredient, the cytokine activity enhancer: STR1 wherein R1 is H, --CH3, --CH2 CH(CH3)OH or --CH2 CH2 OH; R2 is H, --CH3, --CH2 CH3 or --COOH; and R3 is H, --CH3, --CH2 CH3 or --CH2 NH2.
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- The synthesis of potent marcocyclic renin inhibitors
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An efficient synthesis of a novel class of potent macrocylic renin inhibitors exemplified by compounds 1 and 2, which involves the marcocyclization of 8 and 9 as the key step, is described. The macrocyclic design of renin inhibitors 1 and 2 disclosed here
- Dhanoa, Daljit S.,Parsons, William H.,Greenlee, William J.,Patchett, Arthur A.
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p. 1725 - 1728
(2007/10/02)
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- PREPARATION OF 1-AMINOBUTAN-2-OL ENANTIOMERS
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A method of obtaining enantiomers of 1-amino-butan-2-ol through resolution of racemic 1-N-benzylaminobutan-2-ol with tartaric acid and catalytic debenzylation of the synthesized isomers have been developed.Optical purity of the obtained compounds has been
- Gajewczyk, Leonard,Zejc, Alfred
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p. 567 - 571
(2007/10/02)
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- Process for delaying the formation and/or reducing the agglomeration tendency of hydrates
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The invention concerns a process for delaying the formation and/or reducing the agglomeration tendency of hydrates in conditions under which a hydrate may be formed, these hydrates being formed from water and gas. The process according to the invention wherein, in particular, an additive comprising at least one compound from the group of hydroxycarbylamides of substituted carboxylic acids is used. Application of the process according to the invention to processes using gases and water, which form hydrates between them, in particular in the petroleum or gas industry.
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- Herbicidal oxazolidines and methods of use
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An oxazolidine having the formula STR1 wherein R is selected from the group consisting of alkyl, substituted alkyl, alkenyl, cycloalkyl, benzyl, alkoxyalkyl, carboalkoxyalkyl, alkylthioalkyl, phenyl, substituted phenyl, furanyl, phenoxyalkyl, carboalkoxy, substituted phenoxyalkyl, alkylamino, alkoxy, chloroethylamino, alkylthio, cycloalkylalkyl, cycloalkenylalkyl, phenylamino, substituted phenylamino, alkenylamino, and benzylamino; Z is selected from the group consisting of oxygen or sulfur; R1 is selected from the group consisting of alkyl or halosubstituted alkyl wherein the alkyl group has from 1 to 4 carbon atoms; and X and Y are the same or different and are selected from the group consisting of trifluoromethyl, chloro, bromo, fluoro, hydrogen, cyano, alkyl, thioalkyl, halothioalkyl, alkoxy and sulfonylalkyl, wherein the alkyl groups in each alkyl-containing moiety have from 1 to 4 carbon atoms. Also disclosed is a method of use.
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- PROTECTION OF PRIMARY AND SECONDARY AMINES IN THE HYDROBORATION REACTION
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Trimethylsilyl groups are efficient to protect the N-H bonds of olefinic amines in the hydroboration reaction with BMS; deprotection is easily run with methanol and affords aminoorganoboranes which can be used without any oxydation.
- Dicko, A.,Montury, M.,Baboulene, M.
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p. 6041 - 6044
(2007/10/02)
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