The important role of (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Asymmetric synthesis and enantioselectivity of binding of 1-aryl-1,2,3,4-tetrahydroisoquinolines at the PCP site of the NMDA receptor complex

A new method for the asymmetric synthesis of 1-substituted tetrahydroisoquinolines is presented. It is based on stereoselective addition reactions of organometallic compounds to the intermediate N-acylimimum ion 6, which is provided with an N-acyl group as a chiral auxiliary. In addition reactions with organomagnesium and organozinc reagents diastereoselectivities from 70:30 to 95:5 (for 7/8) were observed with the zinc reagents in general leading to markedly improved stereoselectivities. By catalytic hydrogenation of 7 and 8 and after removal of the chiral auxiliary the target compounds 11 and 12 were obtained. The enantiomerically pure 11c-g and 12c-g (ee > 99%), 1-aryltetrahydroisoquinolines, were evaluated for their affinity to the PCP [1-(1-phenylcyclohexyl)piperidine] binding site of the NMDA (N-methyl D-aspartate) receptor. In each case the enantiomers 11 exhibited a higher affinity than those of 12, with the potencies of the enantiomers differing by a factor of 4 (11/12g) to 27 (11/12c). The absolute configuration of the more potent enantiomers 11 is in accordance with the stereochemical requirement found for FR 115427 (3) which is a close analogue.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Discovery of 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. HPLC of Formula: C15H19NO4, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 166591-85-1, in my other articles.

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Structure, function, and mechanism of proline utilization A (PutA)

Proline has important roles in multiple biological processes such as cellular bioenergetics, cell growth, oxidative and osmotic stress response, protein folding and stability, and redox signaling. The proline catabolic pathway, which forms glutamate, enables organisms to utilize proline as a carbon, nitrogen, and energy source. FAD-dependent proline dehydrogenase (PRODH) and NAD+-dependent glutamate semialdehyde dehydrogenase (GSALDH) convert proline to glutamate in two sequential oxidative steps. Depletion of PRODH and GSALDH in humans leads to hyperprolinemia, which is associated with mental disorders such as schizophrenia. Also, some pathogens require proline catabolism for virulence. A unique aspect of proline catabolism is the multifunctional proline utilization A (PutA) enzyme found in Gram-negative bacteria. PutA is a large (>1000 residues) bifunctional enzyme that combines PRODH and GSALDH activities into one polypeptide chain. In addition, some PutAs function as a DNA-binding transcriptional repressor of proline utilization genes. This review describes several attributes of PutA that make it a remarkable flavoenzyme: (1) diversity of oligomeric state and quaternary structure; (2) substrate channeling and enzyme hysteresis; (3) DNA-binding activity and transcriptional repressor function; and (4) flavin redox dependent changes in subcellular location and function in response to proline (functional switching).

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Brief introduction of 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

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Visible-Light Photoredox-Catalyzed Decarboxylative Alkylation of Heteroarenes Using Carboxylic Acids with Hydrogen Release

Herein, we have developed visible-light photoredox-catalyzed decarboxylating carboxylic acids for alkylation of heteroarenes under mild conditions. The transformation occurred smoothly without the requirement of stoichiometric oxidants in the presence of 0.3 equiv of base, which benefited from the release of hydrogen (H2) and carbon dioxide (CO2). Various substrates and functional groups were tolerated. Primary mechanistic studies suggest that an oxidative quenching pathway and a reductive quenching pathway are both possible in the catalytic cycle.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Discovery of 149353-95-7

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Application of 149353-95-7, A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 149353-95-7, Name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid, molecular formula is C15H19NO4. In a Article£¬once mentioned of 149353-95-7

RGD mimetics containing phthalimidine fragment as novel ligands of fibrinogen receptor

The novel RGD mimetics with phthalimidine central fragment were synthesized with the use of 4-piperidine-4-yl-butyric, 4-piperidine-4-yl-benzoic, 4-piperazine-4-yl-benzoic and 1,2,3,4-tetrahydroisoquinoline-7-carboxylic acids as surrogates of Arg motif. The synthesized compounds potently inhibited platelet aggregation in vitro and blocked FITC-Fg binding to alphaIIbbeta3 integrin in a suspension of washed human platelets. The key alphaIIbbeta3 protein-ligand interactions were determined in docking experiments.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Discovery of 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

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Method of racemization of optically active tetrahydrofuran-2-carboxylic acid

Disclosed is a method of racemization of optically active tetrahydrofuran-2-carboxylic acid. (+)-Tetrahydrofuran-2-carboxylic acid is useful as a side chain intermediate of the antibiotics of penem series, and is prepared by optical resolution of racemic compound. The remaining (+)-isomer should be racemized and reused as the material for further optical resolution. The racemization can be, in accordance with the present invention, carried out by heating the optically active tetrahydrofuran-2-carboxylic acid to a temperature of 100 C. or higher in the presence of a strong base.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Discovery of 6-Chloro-1,2,3,4-tetrahydroisoquinoline hydrochloride

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DERIVATIVES OF 4-(N-AZACYCLOALKYL) ANILIDES AS POTASSIUM CHANNEL MODULATORS

This invention provides a compound of formula IAwhere X?O or S; Y is O or S; q=1 or 0; and other substituents are defined herein. Such compounds can affect the opening of, or otherwise modulate, voltage-gated potassium channels. They are potentially useful for the treatment and prevention of diseases and disorders which are affected by activation or modulation of potassium ion channels. One such condition is seizure disorders.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Awesome and Easy Science Experiments about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

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Structure and Mechanism of Titania-Supported Platinum-Molybdenum Catalyst for Hydrodeoxygenation of 2-Furancarboxylic Acid to Valeric Acid

Selective hydrodeoxygenation of 2-furancarboxylic acid, which can be a relatively stable platform chemical from hemicellulose, to valeric acid was investigated in detail, and the reaction has been reported to be specifically promoted by supported Pt-MoOx catalysts. The dependence of catalytic performance of Pt-MoOx/TiO2 on loading amounts of Pt and Mo showed that the highest activity is obtained at around Mo ?0.5 wt % when the Pt loading amount is fixed. With enough of the catalyst that can minimize the effect of deactivation, ?60% yield of valeric acid was obtained over all Pt-MoOx/TiO2 catalysts with Pt ? 1 wt % and 0.5 wt % Mo loadings. Characterization results of Pt-MoOx/TiO2 catalysts with XRD and CO adsorption showed that the Pt particles (3-5 nm, depending on Pt loading amount) were not covered with MoOx species, suggesting that MoOx species were mainly located on the TiO2 support surface. Mo K-edge XAFS results suggest that the MoOx species in Pt-MoOx/TiO2 have a Mo(IV) valence state and some of the MoIVOx species have direct bonds with the Pt atom on Pt metal particles. The number of the direct Pt-Mo bonds became smaller after catalytic use, which can be related to the deactivation. Therefore, the Pt-Mo bimetallic site can be the catalytically active site. Based on the solvent effect, reactivity trends of related substrates, and reaction orders in kinetics, a reaction mechanism is proposed where the ring is opened after addition of one hydrogen atom to the 2-position of the furan ring.

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Tetrahydroisoquinoline – Wikipedia,
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Archives for Chemistry Experiments of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Cobalt-Catalyzed oxidative alpha-cyanation of tertiary aromatic amines with trimethylsilyl cyanide and tert -butyl hydroperoxide

In this Letter is described that a cobalt(II)-tert-butyl hydroperoxide oxidizing system was used to catalyze the alpha-cyanation of aromatic tertiary amines in the presence of trimethylsilyl cyanide to produce the corresponding alpha-aminonitriles in good yields. Georg Thieme Verlag Stuttgart. New York.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Brief introduction of 118864-75-8

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One-Pot N-Deprotection and Catalytic Intramolecular Asymmetric Reductive Amination for the Synthesis of Tetrahydroisoquinolines

A one-pot N-Boc deprotection and catalytic intramolecular reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: Titanium(IV) isopropoxide and molecular iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

New explortion of 3340-78-1

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CuBr-catalyzed oxidative difluoromethylation of tertiary amines with difluoroenol silyl ethers

CuBr-catalyzed oxidative difluoromethylation of readily available tertiary amines with difluoroenol silyl ethers was performed under mild conditions to afford beta-amine-a,a-difluoro ketones.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem