64658-22-6Relevant articles and documents
Design and Synthesis of N-Aryl Phenoxyethoxy Pyridinones as Highly Selective and CNS Penetrant mGlu3 NAMs
Engers, Julie L.,Bollinger, Katrina A.,Weiner, Rebecca L.,Rodriguez, Alice L.,Long, Madeline F.,Breiner, Megan M.,Chang, Sichen,Bollinger, Sean R.,Bubser, Michael,Jones, Carrie K.,Morrison, Ryan D.,Bridges, Thomas M.,Blobaum, Anna L.,Niswender, Colleen M.,Conn, P. Jeffrey,Emmitte, Kyle A.,Lindsley, Craig W.
, p. 925 - 930 (2017)
Herein, we detail the optimization of the mGlu3 NAM, VU0650786, via a reductionist approach to afford a novel, simplified mGlu3 NAM scaffold that engenders potent and selective mGlu3 inhibition (mGlu3 IC50
Access to Optically Enriched α-Aryloxycarboxylic Esters via Carbene-Catalyzed Dynamic Kinetic Resolution and Transesterification
Liu, Bin,Song, Runjiang,Xu, Jun,Majhi, Pankaj Kumar,Yang, Xing,Yang, Song,Jin, Zhichao,Chi, Yonggui Robin
, p. 3335 - 3338 (2020/04/30)
Optically active α-aryloxycarboxylic acids and their derivatives are important functional molecules. Disclosed here is a carbene-catalyzed dynamic kinetic resolution and transesterification reaction for access to this class of molecules with up to 99% yields and 99:1 er values. Addition of a chiral carbene catalyst to the ester substrate leads to two diastereomeric azolium ester intermediates that can quickly epimerize to each other and thus allows for effective dynamic kinetic resolution to be realized. The optically enriched ester products from our reaction can be quickly transformed to chiral herbicides and other bioactive molecules.
PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
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Page/Page column 163, (2020/01/11)
Disclosed are compounds of Formula I, including pharmaceutically acceptable salts, pharmaceutical compositions comprising the compounds, methods for making the compounds and their use in inhibiting HIV integrase and treating those infected with HIV or AIDS.
Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature
Rasu, Loorthuraja,John, Jeremy M.,Stephenson, Elanna,Endean, Riley,Kalapugama, Suneth,Clément, Roxanne,Bergens, Steven H.
supporting information, p. 3065 - 3071 (2017/03/11)
High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized α-phenoxy and related amides at room temperature under 4 atm H2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.
CATALYSTS AND PROCESSES FOR THE HYDROGENATION OF AMIDES
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Paragraph 0274; 0275; 0276; 0277; 0278; 0279, (2014/06/24)
There is provided a process for the reduction of one or more amide moieties in a compound comprising contacting the compound with hydrogen gas and a transition metal catalyst in the presence or absence of a base under conditions for the reduction an amide bond. The presently described processes can be performed at low catalyst loading using relatively mild temperature and pressures, and optionally, in the presence or absence of a base or high catalyst loadings using low temperatures and pressures and high loadings of base to effect dynamic kinetic resolution of achiral amides.
Preparation of novel chiral non-racemic diselenides and applications in asymmetric synthesis
Zhao, Liwei,Li, Zhong,Wirth, Thomas
experimental part, p. 176 - 182 (2011/03/22)
New chiral non-racemic diselenides were prepared and their corresponding selenium electrophiles were used for thestereoselective functionalization of alkenes. The influence of different nucleophiles on the outcome of the selenenylation reaction was studie
Enantioselective synthesis of chiral β-aryloxy alcohols by asymmetric hydrogenation of a-aryloxy aldehydes via dynamic kinetic resolution
Zhou, Zhang-Tao,Xie, Jian-Hua,Zhou, Qi-Lin
supporting information; experimental part, p. 363 - 366 (2009/11/30)
A catalytic enantioselective hydrogenation of racemic α-aryloxy aldehydes via dynamic kinetic resolution has been developed by using (diamine)(spirodiphosphine)ruthenium(II) chloride [RuCl 2(SDPs)(diamine)] catalysts. Employing this new reactio
Highly enantioselective kinetic resolution of primary alcohols of the type Ph-X-CH(CH3)-CH2OH by Pseudomonas cepacia lipase: Effect of acyl chain length and solvent
Mezzetti, Alessandra,Keith, Curtis,Kazlauskas, Romas J.
, p. 3917 - 3924 (2007/10/03)
Although lipase from Pseudomonas cepacia (PCL) shows high enantioselectivity towards many secondary alcohols, it usually exhibits only low to moderate enantioselectivity towards primary alcohols. To increase this enantioselectivity, we optimised the reaction conditions for the PCL-catalysed hydrolysis of esters of three chiral primary alcohols: 2-methyl-3-phenyl-1- propanol 1, 2-phenoxy-1-propanol 2 and solketal 3. The enantioselectivity towards 1-acetate increased from E=16 to 38 upon changing the solvent from ethyl ether/phosphate buffer to 30% n-propanol in phosphate buffer and increased again to E ≥190 upon changing the substrate from 1-acetate to 1-heptanoate. The same changes increased the enantioselectivity towards alcohol 2 from E=17 to 70, but did not significantly increase the enantioselectivity towards alcohol 3. The best solvent was similar to the solvent used to crystallise the open form of PCL and likely stabilises the open form of PCL. This stabilisation may increase the enantioselectivity by removing kinetic contributions from a non-enantioselective lid-opening step. We determined the kinetic contribution of the lid-opening step by measuring the interfacial activation of PCL. The activation energy for the PCL-catalysed hydrolysis of ethyl acetate was at least 2.6 kcal/mol lower in the presence of a water-organic solvent interface.
Resolution of 2-aryloxy-1-propanols via lipase-catalyzed enantioselective acylation in organic media
Miyazawa, Toshifumi,Yukawa, Tomoyuki,Koshiba, Takashi,Sakamoto, Hiroko,Ueji, Shinichi,Yanagihara, Ryoji,Yamada, Takashi
, p. 1595 - 1602 (2007/10/03)
2-Aryloxy-1-propanols, primary alcohols with an oxygen atom at the stereocenter, were resolved with good to high enantioselectivity by acylation with vinyl butanoate mediated by Pseudomonas sp. lipase in di-iso-propyl ether. Potential factors affecting the enantioselectivity of the enzymatic acylation were examined: solvents, acyl donors and temperature. Using this enantioselective acylation procedure, enantiomerically pure (R)-2-(4-chlorophenoxy)-1-propanol was prepared on a gram scale.
Synthesis of novel acridino- and phenazino-18-crown-6 ligands and their optically pure dimethyl-substituted analogues for molecular recognition studies
Huszthy, Peter,Samu, Erika,Vermes, Borbala,Mezey-Vandor, Gabriella,Nogradi, Mihaly,Bradshaw, Jerald S.,Izatt, Reed M.
, p. 1491 - 1504 (2007/10/03)
Novel acridino- and phenazino-18-crown-6 ligands 5 and 6 were prepared from acridine-4.5-diol (9) and phenazine-1,9-diol (10) with tetraethylene glycol di-p-tosylate (11) using potassium tert-butoxide as a base in THF. New optically pure dimethyl-substitu
