1315360-79-2Relevant articles and documents
Simple Tetrahydroisoquinolines Are Potent and Selective Kappa Opioid Receptor Antagonists
Kormos, Chad M.,Ondachi, Pauline W.,Runyon, Scott P.,Thomas, James B.,Mascarella, S. Wayne,Decker, Ann M.,Navarro, Hernán A.,Carroll, F. Ivy
, p. 742 - 745 (2017)
Potent and selective κ opioid receptor antagonists have been derived from the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine class of pure opioid receptor antagonists. In order to determine if the 3-hydroxyphenyl and/or the piperidine amino groups are required for obtaining the pure opioid antagonists, (3R)-7-hydroxy-N-[(1S)-2-methyl-1-(piperidine-1-ylmethyl)propyl]-1,2,3,4-tetrahydroiosquinoline-3-carboxamide (1), which does not have a 4-(3-hydroxyphenyl) group, and (3R)-N-(1R)-1-(cyclohexylmethyl)-2-methylpropyl]-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamide (2), which does not have a 4-hydroxylphenyl or a piperidine amino group, were synthesized and evaluated for their [35S]GTPγS binding properties at the μ, δ, and κ opioid receptors. Surprisingly compound 1 remained a pure opioid antagonist with a Ke = 6.80 nM at the κ opioid receptor and is 21- and 441-fold selective for the κ receptor relative to the μ and δ opioid receptors, respectively. Even more unexpected and novel is the finding that 2 has a Ke = 0.14 nM at κ and is 1730- and 4570-fold selective for κ relative to the μ and δ opioid receptors, respectively.
GLYCINE REUPTAKE INHIBITOR AND USE THEREOF
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Paragraph 0062; 0066, (2015/05/26)
Disclosed are a glycine reuptake inhibitor and the use thereof. The glycine reuptake inhibitor is a compound of formula I, or isomers, pharmaceutically acceptable salts or solvates thereof, wherein R1 is one or more groups selected from hydrogen, halogen,
Enantioselective Synthesis of Dialkylated α-Hydroxy Carboxylic Acids through Asymmetric Phase-Transfer Catalysis
Duan, Shaobo,Li, Sanliang,Ye, Xinyi,Du, Nuan-Nuan,Tan, Choon-Hong,Jiang, Zhiyong
supporting information, p. 7770 - 7778 (2015/08/18)
In the presence of an L-tert-leucine-derived urea-ammonium salt as phase-transfer catalyst, a highly enantioselective alkylation of 5H-oxazol-4-ones with various benzyl bromides and allylic bromides has been developed to furnish catalytic asymmetric synthesis of biologically important dialkylated α-hydroxy carboxylic acids with a broad scope. This is the first example of an L-amino acid-derived urea-ammonium salt being used as a phase-transfer catalyst with excellent catalytic efficiency.
GLYCINE REUPTAKE INHIBITOR AND USE THEREOF
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Paragraph 0058; 0062, (2014/10/15)
Disclosed are a glycine reuptake inhibitor and the use thereof. The glycine reuptake inhibitor is a compound of formula I, or isomers, pharmaceutically acceptable salts or solvates thereof, wherein R1 is one or more groups selected from hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy, nitro, cyano, amino, hydroxyl, C1-6 haloalkyl, and C1-6 haloalkoxy; R2 is selected from hydrogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, and C1-6 haloalkoxy; and each of R3 and R4 is independently selected from hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy, nitro, cyano, amino, hydroxyl, C1-6 haloalkyl, and C1-6 haloalkoxy.
Highly active chiral phosphoramide-Zn(II) complexes as conjugate acid-base catalysts for enantioselective organozinc addition to ketones
Hatano, Manabu,Miyamoto, Takashi,Ishihara, Kazuaki
, p. 4535 - 4538 (2008/03/12)
(Chemical Equation Presented) A highly efficient enantioselective organozinc (R2Zn) addition to ketones catalyzed by chiral phosphoramide-Zn(II) complexes (1-10 mol %) has been developed. These complexes serve as conjugate Lewis acid-Lewis base
Enantioselective conjugate addition to cyclic enones with scalemic lithium organo(amido)cuprates, part IV. Relationship between ligand structure and enantioselectivity
Rossiter, Bryant E.,Eguchi, Masakatsu,Miao, Guobin,Swingle, Nicole M.,Hernandez, Amelia E.,Vickers, Denise,Fluckiger, Ezdan,Greg Patterson,Vasavi Reddy
, p. 965 - 986 (2007/10/02)
Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products with up to 97% ee. Nonlinear asymmetric induction was observed with the cuprate formed from ligand 13.
