Properties and Exciting Facts About 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Benzanilide-biphenyl replacement: A bioisosteric approach to quinoline carboxamide-type ABCG2 modulators

Recently reported compounds such as UR-COP78 (6) are among the most potent and selective ABCG2 modulators known so far but are prone to rapid enzymatic cleavage at the central benzanilide moiety. In search for more stable analogues, according to a bioisosteric approach, a series of N-(biphenyl-3-yl)quinoline carboxamides was prepared by solid phase and solution phase synthesis. The biphenyl moiety was constructed by Suzuki coupling. Inhibition of ABCB1 and ABCG2 was determined in a calcein-AM and a Hoechst 33342 microplate assay, respectively. Most synthesized compounds selectively inhibited the ABCG2 transporter at submicromolar concentrations with a maximal inhibitory effect (Imax) over 90% (e.g., UR-COP228 (22a), IC50 591 nM, Imax 109%; UR-COP258 (31), IC50 544 nM, Imax 112%), though with lower potency and selectivity than 6. The biphenyl analogues are considerably more stable and demonstrate that the benzanilide core is not a crucial structural feature of quinoline carboxamide-type ABCG2 modulators.

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

Extended knowledge of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Synthesis of functionalized nitrogen heterocycles from beta- And gamma-amino acids by radical decarboxylation

The radical decarboxylation of beta- and gamma-amino acids on treatment with PhI(OAc)2a-I2 is a mild and efficient methodology to synthesize halogenated or oxygenated nitrogen heterocycles. The reaction was applied to the synthesis of bioactive products, such as opioid analogues, iminosugars and new antifungic agents.

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

Final Thoughts on Chemistry for 1,2,3,4-Tetrahydroisoquinoline-7-carbonitrile

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Synthetic Route of 149355-52-2, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.149355-52-2, Name is 1,2,3,4-Tetrahydroisoquinoline-7-carbonitrile, molecular formula is C10H10N2. In a Patent£¬once mentioned of 149355-52-2

BICYCLIC BENZAMIDE COMPOUNDS AS HISTAMINE H3 RECEPTOR LIGAND USEFUL IN THE TREATMENT OF NEUROLOGICAL DISEASES

The present invention relates to novel bicyclic benzamide derivatives having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of neurological and psychiatric disorders.

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

Brief introduction of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Novel 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran derivatives as selective alpha2C-adrenergic receptor antagonists

The synthesis of a series of 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methyl-2-arylbenzofuran and 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran-2-carboxamide derivatives as novel alpha2C-adrenergic receptor antagonists are described. Their affinity at three different human alpha2-adrenergic receptors is reported, and some of these compounds exhibited high affinity for the alpha2C-adrenergic receptor with high subtype selectivity. Among them, compound 10e has been found to show the anti-l-dopa-induced dyskinetic activity in marmosets. The structure-activity relationship of these compounds is also discussed.

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Tetrahydroisoquinoline – Wikipedia,
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Simple exploration of 7-Methoxy-1,2,3,4-tetrahydroisoquinoline

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Application of 43207-78-9, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.43207-78-9, Name is 7-Methoxy-1,2,3,4-tetrahydroisoquinoline, molecular formula is C10H13NO. In a Article£¬once mentioned of 43207-78-9

Inhibition of monoamine oxidase by isoquinoline derivatives. Qualitative and 3D-quantitative structure-activity relationships

A series of isoquinolines, N-methyl-1,2-dihydroisoquinolines, N-methyl-1,2,3,4-tetrahydroisoquinolines, 1,2,3,4-tetrahydroisoquinolines, and N-methylisoquinolinium ions were tested as inhibitors of monoamine oxidases A and B. All compounds were found to act as reversible and time-independent MAO inhibitors, often with a distinct selectivity towards MAO-A. As a class, the N-methylisoquinolinium ions were found to be the most active MAO-A inhibitors, with N-methyl-6-methoxyisoquinolinium ion emerging as a potent (IC50 = 0.81 muM) and competitive MAO-A inhibitor. Comparative molecular field analysis (CoMFA, a 3D-QSAR method) of MAO-A inhibition was performed using the data reported here and in the literature. Using the steric and lipophilic fields of the inhibitors, quantitative models with reasonable predictive power were obtained that point to the importance of steric, lipophilic, and polar interactions in modulating MAO-A inhibitory activity.

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

Brief introduction of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Synthesis and characterization of 5,6,7,8-tetrahydroquinoline C5a receptor antagonists

A novel series of substituted 2-aryl-5-amino-5,6,7,8-tetrahydroquinoline C5a receptor antagonists is reported. Synthetic routes were developed that allow the substituents on the tetrahydroquinoline core to be efficiently varied, facilitating determination of structure-activity relationships. Members of the series display high binding affinity for the C5a receptor and are potent functional antagonists.

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

New explortion of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Integrating Hydrogen Production with Aqueous Selective Semi-Dehydrogenation of Tetrahydroisoquinolines over a Ni2P Bifunctional Electrode

Exploring an alternative anodic reaction to produce value-added chemicals with high selectivity, especially integrated with promoted hydrogen generation, is desirable. Herein, a selective semi-dehydrogenation of tetrahydroisoquinolines (THIQs) is demonstrated to replace the oxygen evolution reaction (OER) for boosting H2 evolution reaction (HER) in water over a Ni2P nanosheet electrode. The value-added semi-dehydrogenation products, dihydroisoquinolines (DHIQs), can be selectively obtained with high yields at the anode. The controllable semi-dehydrogenation is attributed to the in situ formed NiII/NiIII redox active species. Such a strategy can deliver a variety of DHIQs bearing electron-withdrawing/donating groups in good yields and excellent selectivities, and can be applied to gram-scale synthesis. A two-electrode Ni2P bifunctional electrolyzer can produce both H2 and DHIQs with robust stability and high Faradaic efficiencies at a much lower cell voltage than that of overall water splitting.

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Tetrahydroisoquinoline – Wikipedia,
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Properties and Exciting Facts About 1612-65-3

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Application of 1612-65-3, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.1612-65-3, Name is 2-Methyl-1,2,3,4-tetrahydroisoquinoline, molecular formula is C10H13N. In a Article£¬once mentioned of 1612-65-3

Solvent Effects on Lower Excited States of N-Methyl-1,2,3,4-tetrahydroisoquinoline

The electronic spectra of the title compound, N-methyl-1,2,3,4-tetrahydroisoquinoline (NMTHIQ), i.e., a bichromophoric molecule with benzene and tertiary alkylamine groups, were observed in various media.Five or more absorption bands as well as two kinds of fluorescences were observed.These were assigned to transitions involving 1La and 1Lb states of the benzene (Ph) group, two kinds of Rydberg states of the amine (N) group, and a Ph* <- nN type charge-transfer (CT) state, consistent with observed solvent effects.Excitation-wavelength dependences of fluorescence quantum yields were also measured, indicating peculiar solvent effects on both radiative and radiationless transitions, especially on a fast internal conversion from the 1Lb state to the ground state, probably via the CT state.The protonation effect on the amine group is apparently inconsistent with an earlier idea that the amine group suffers hypsochromic effect when it is protonated.This result was explained by assuming a double-minimum potential well for the hydrogen-bond structures: < formular>; the latter conformation gives a novel protonation effect preserving the electron-donating nN orbital.

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

Awesome Chemistry Experiments For 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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SELECTIVE REMOVAL OF THE TERT-BUTOXYCARBONYL GROUP FROM SECONDARY AMINES: ZnBr2 AS THE DEPROTECTING REAGENT

ZnBr2 in dichloromethane is a convenient reagent for mild and selective removal of the tert-butoxycarbonyl group from secondary amines.

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

Extracurricular laboratory:new discovery of 43207-78-9

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Inhibition of phenylethanolamine n-methyltransferase (PNMT) by aromatic hydroxy-substituted 1,2,3,4-tetrahydroisoquinolines: Further studies on the hydrophilic pocket of the aromatic ring binding region of the active site

In a continuation of studies directed toward characterizing the hydrophilic pocket within the aromatic ring binding region of the active site of phenylethanolamine N-methyltransferase (PNMT), 5-, 6-, 7-, and 8-hydroxy-1,2,3,4-tetrahydroisoquinoline were prepared and evaluated as substates and inhibitors of PNMT. In order to discern the necessity of an acidic hydrogen for interaction at this pocket the corresponding methyl ethers were also evaluated. The enhanced affinity of 7-hydroxy-1,2,3,4-tetrahydroisoquinoline (16) versus tetrahydroisoquinoline (13) itself indicates that a hydrophilic pocket exists off of carbon C7 in bound tetrahydroisoquinolines. The diminished affinity of the corresponding methyl ether is consistent with a requirement for the acidic hydrogen of 16 for interaction of the aromatic hydroxyl at site. From the relative activities of the other regioisomeric aromatic hydroxyl-substituted tetrahydroisoquinolines, their corresponding methyl ethers, and 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, it appears that the hydrophilic pocket is spatially compact with respect to bound tetrahydroisoquinolines and is surrounded by larger areas of lipophilic character. To allow a comparison of the results of this study with previous data on bound beta-phenylethylamines, the methyl ethers of 5-, 6-, 7-, and 8-hydroxy-exo-2-aminobenzonorbornene and of 5- and 6-hydroxy-anti-9-aminobenzonorbornene were also evaluated for their activity as substrates and inhibitors for PNMT. The results of this study are in agreement with previous findings for bound beta-phenylethylamines and support the conclusion that the natural substrate for PNMT, norepinephrine, has a different active site binding orientation than most known substrates and competitive inhibitors of the enzyme.

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