89232-30-4Relevant academic research and scientific papers
Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides
Dixon, Darren J.,Formica, Michele,Hamlin, Trevor A.,Rozsar, Daniel,Yamazaki, Ken
supporting information, p. 1006 - 1015 (2022/02/03)
The first metal-free catalytic intermolecular enantioselective Michael addition to unactivated α,β-unsaturated amides is described. Consistently high enantiomeric excesses and yields were obtained over a wide range of alkyl thiol pronucleophiles and elect
Synthesis of 2,3-dihydroxy-3-(N-substituted carbamoyl)propylphosphonic acid derivatives as hybrid DOXP-fosmidomycin analogues
Blatch, Gregory L.,Kaye, Perry T.,Klein, Rosalyn,Lobb, Kevin A.,Mutorwa, Marius K.
, (2022/02/05)
A six-step synthetic pathway has been established to access a series of racemic 2,3-dihydroxy-3-(N-substituted carbamoyl)propylphosphonic acid derivatives, designed to contain structural features common to both the natural substrate 1-deoxy-D-xylulose 5-p
Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids
Ramachandran, P. Veeraraghavan,Hamann, Henry J.
supporting information, p. 2938 - 2942 (2021/05/04)
Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.
CARBAMOYLOXYMETHYL TRIAZOLE CYCLOHEXYL ACIDS AS LPA ANTAGONISTS
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Paragraph 1002-1004, (2018/01/18)
The present invention provides compounds of Formula (I): or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein all the variables are as defined herein. These compounds are selective LPA receptor inhibitors.
Thermodynamically controlled chemoselectivity in lipase-catalyzed aza-Michael additions
Rivera-Ramírez, José Domingo,Escalante, Jaime,López-Munguía, Agustín,Marty, Alain,Castillo, Edmundo
supporting information, p. 76 - 82 (2015/01/30)
Chemoselective synthesis of N-protected β-amino esters involving lipase-catalyzed aza-Michael additions and α,β-unsaturated precursors is mainly hampered by the two electrophilic sites present on these compounds. In order to control the chemoselectivity a solvent engineering strategy based on the thermodynamic behaviour of products in media of different polarity was designed. This strategy allowed to obtain aza-Michael adducts from benzylamine and different acrylates with high selectivity. In almost all reactions carried out in n-hexane, a non-polar solvent, aminolysis was avoided while the corresponding Michael adducts were exclusively synthesized in 53-78% yields. On the contrary, in reactions carried out in a polar solvent such as 2-methyl-2-butanol the aminolysis products were favoured. Thermodynamic analyses of these processes using the COSMO-RS method helped to understand some of the key factors affecting chemoselectivity and confirmed that a reliable estimation of the thermodynamic interactions of solutes and solvents allows an adequate selection of a reaction media that may lead to chemoselectivity.
Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base
Wang, Feng,Yang, Haijun,Fu, Hua,Pei, Zhichao
supporting information, p. 517 - 519 (2013/02/23)
A novel and efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base has been developed. The protocol uses readily available acrylic derivatives and primary alcohols as the starting materials, inexpensive CuCl2 as the catalyst, and the corresponding addition products were obtained in moderate to excellent yields.
Discovery and SAR of isonicotinamide BACE-1 inhibitors that bind β-secretase in a N-terminal 10s-loop down conformation
Stauffer, Shaun R.,Stanton, Matthew G.,Gregro, Alison R.,Steinbeiser, Melissa A.,Shaffer, Jennifer R.,Nantermet, Philippe G.,Barrow, James C.,Rittle, Kenneth E.,Collusi, Dennis,Espeseth, Amy S.,Lai, Ming-Tain,Pietrak, Beth L.,Holloway, M. Katharine,McGaughey, Georgia B.,Munshi, Sanjeev K.,Hochman, Jerome H.,Simon, Adam J.,Selnick, Harold G.,Graham, Samuel L.,Vacca, Joseph P.
, p. 1788 - 1792 (2008/02/02)
A series of low-molecular weight 2,6-diamino-isonicotinamide BACE-1 inhibitors containing an amine transition-state isostere were synthesized and shown to be highly potent in both enzymatic and cell-based assays. These inhibitors contain a trans-S,S-methyl cyclopropane P3 which bind BACE-1 in a 10s-loop down conformation giving rise to highly potent compounds with favorable molecular weight and moderate to high susceptibility to P-glycoprotein (P-gp) efflux.
Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of alzheimer's disease
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Page/Page column 19, (2008/06/13)
The present invention is directed to phenylamide and pyridylamide derivative compounds of which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.
BENZYLETHER AND BENZYLAMINO BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
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Page/Page column 42, (2010/02/11)
The present invention is directed to benzylether and benzylamino derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.
2, 4, 6-SUBSTITUTED PYRIDYL DERIVATIVE COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER’S DISEASE
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Page/Page column 48, (2010/02/14)
The present invention is directed to 2, 4, 6-substituted pyridyl derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer’s disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.
