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

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Discovery of novel N-sulfonamide-tetrahydroquinolines as potent retinoic acid receptor-related orphan receptor gammat inverse agonists for the treatment of autoimmune diseases

Targeting the nuclear receptor RORgammat is thought to be effective in autoimmune disorders. Tertiary sulfonamide 1 was found to be a potent RORgammat inverse agonist previously. However, the high hepatic clearance value limits its druggability. In this study, we designed and synthesized a series of N-sulfonamide-tetrahydroquinolines by molecular modeling and scaffold hopping strategy, aiming at improving the metabolic stabilities. Detailed SAR exploration led to identification of potent RORgammat inverse agonists such as 13 with moderate binding affinity and inhibitory activity of Th17 cell differentiation. Binding mode of 13 with RORgammat-LBD was revealed by molecular docking. Moreover, 13 showed lower intrinsic clearance in mouse liver microsomes compared with 1 and potent in vivo efficacy and safety in psoriasis models, which can be used as a good starting point for the further optimization.

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

Simple exploration of 1-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Studies on cerebral protective agents. IX. Synthesis of novel 1,2,3,4- tetrahydroisoquinolines as N-methyl-D-aspartate antagonists

A series of 1,2,3,4-tetrahydroisoquinoline derivatives were synthesized and evaluated for anticonvulsant activity against intracerebro-ventriculas (i.c.v.) N-methyl-D-aspartate (NMDA)-induced seizures in mice. Among these compounds, (+)-1-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride ((+)-1a, FR115427) was the most effective anticonvulsant, and also protected CA1 hippocampal neurons from ischemia-induced neuronal degeneration in rats at 32 mg/kg i.p. In addition, (+)-1a showed anti-hypoxic activity in mice at 3.2-32 mg/kg i.p. The absolute configuration at the C-1 position of the isoquinoline ring was determined to be S by a single-crystal X-ray analysis of (+)-1a (+)-di-p-toluoyl-D-tartrate. Structure-activity relationships with regard to the anticonvulsant activity of this series of compounds are discussed, and the three-dimensional structures of (s)-(+)-1a and MK801 are compared.

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Reference£º
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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Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes from readily available carboxylic acids at room temperature under visible-light irradiation. The combination of an iridium photocatalyst with ethynylbenziodoxolone (EBX) reagents allowed the decarboxylative alkynylation of carboxylic acids in good yields under mild conditions. The method could be applied to silyl-, aryl-, and alkyl- substituted alkynes. It was particularly successful in the case of alpha-amino and alpha-oxo acids derived from biomass.

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

Properties and Exciting Facts About 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Cu-Catalyzed [4+1] Annulation toward Indolo[2,1-a]isoquinolines through Oxidative C(sp3)/C(sp2)?H Bond Bifunctionalization

A Cu-catalyzed [4+1] annulation of N-aryl-1,2,3,4-tetrahydroisoquinolines (N-aryl THIQs) with alpha-diazoketones has been established under oxidative conditions, leading to the construction of a series of indolo[2,1-a]isoquinolines with generally good yields. The reaction enables dediazotized dicarbonylation of alpha-diazoketones, creating direct C(sp3)/C(sp2)?H bond bifunctionalization to access tetracyclic aza-heterocyclic skeletons.

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

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Synthesis and properties of push-pull imidazole derivatives with application as photoredox catalysts

Two new push-pull molecules with imidazole-4,5-dicarbonitrile acceptor, thiophene and 2-methoxythiophene donors with potential use in photoredox catalysis were designed and prepared. The synthesis started from commercially available imidazole-4,5-dicarbonitrile and its bromination and N-methylation. Subsequent Suzuki-Miyaura cross-coupling with (5-methoxy)thiophene-derived boronic acids afforded target push-pull derivatives. Beside common analytical methods, the molecular structure of 5-methoxythiophen-2-yl derivative has also been verified by X-ray analysis. DSC analyses showed remarkable thermal stabilities of both target derivatives with Tm and TD values above 150 and 270 C, respectively. Fundamental properties and extent of the intramolecular charge-transfer were further studied by UV-VIS absorption spectra and DFT calculations. Fundamental photoredox properties of target imidazole derivatives were elucidated. Both push-pull molecules were preliminary tested as photoredox catalysts in cross-dehydrogenative coupling reaction between tetrahydroisoquinoline and nitromethane and the results were compared with those obtained by pyrazine-2,3-dicarbonitrile-derived catalyst.

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

Extracurricular laboratory:new discovery of 7-Bromo-1,2,3,4-tetrahydroisoquinoline

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Novel 2-aminooctahydrocyclopentalene-3a-carboxamides as potent CCR2 antagonists

Novel CCR2 antagonists with a novel 2-aminooctahydrocyclopentalene-3a- carboxamide scaffold were designed. SAR studies led to a series of potent compounds. For example, compound 51 had a good PK profile in both dog and monkey, and exhibited excellent efficacy when dosed orally in an inflammation model in hCCR2 KI mice. In addition, an asymmetric synthesis to the core structures was developed.

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

Top Picks: new discover of 99365-69-2

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SUBSTITUTED SPIROAMIDE COMPOUNDS

Substituted spiroamide compounds corresponding to formula (I): wherein A, B, Q1, Q2, Q3, Q4, R1, R8, R9a, R9b, R12, R13, R200 and R210 have defined meanings, processes for their preparation, pharmaceutical compositions containing such compounds, and the use of such compounds for treating or inhibiting pain or other conditions mediated at least in part by the bradykinin 1 receptor (B1R)

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

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Metal-organic framework composites with luminescent pincer platinum(II) complexes: 3MMLCT emission and photoinduced dehydrogenation catalysis

Pincer platinum(ii) complexes are well documented to exhibit weak intermolecular interactions in the solid state and 77 K glassy solutions, leading to emissive triplet metal-metal-to-ligand charge transfer (3MMLCT) excited states that often vanish in dilute solutions. In this work, metal-organic framework (MOF) materials are introduced to provide a “solid solution” environment for easy access to 3MMLCT excited states of pincer platinum(ii) complexes. Phosphorescent composites PtII@MOFs (1-4) with matrix-dependent monomers and oligomer emission properties were obtained. These PtII@MOFs are efficient catalysts for photoinduced dehydrogenation reactions.

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

Properties and Exciting Facts About 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Radical alkylation of C(sp3)-H bonds with diacyl peroxides under catalyst-free conditions

Herein, we describe a protocol for alkylation reactions of C(sp3)-H bonds with diacyl peroxides by means of a process involving cross-coupling between an alkyl radical and an alpha-Aminoalkyl radical. The mild, catalyst-And additive-free conditions make this protocol superior to previously reported C(sp3)-H alkylation strategies. The protocol was applied to 1,2,3,4-Tetrahydroisoquinolines and a tetrahydro-beta-carboline derivative and could be carried out on a gram scale, indicating its utility for the alkylation of late-stage synthetic intermediates.

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

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Thieme Chemistry Journal Awardees – Where are they now? Aerobic oxidative coupling of tertiary amines with silyl enolates and ketene acetals

Cyclic tertiary amines can be oxidatively coupled with a variety of silyl enol ethers or ketene acetals to furnish tertiary Mannich bases. The reactions are catalyzed by simple copper salts employing elemental oxygen as the oxidant. Georg Thieme Verlag Stuttgart.

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