Archives for Chemistry Experiments of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Quinazolines derivatives for enhancing antitumor activity

2,4-Diaminoquinazoline derivatives as potentiators of chemotherapeutic agents in the treatment of cancer.

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

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Synthesis and in vitro evaluation of tetrahydroisoquinolines with pendent aromatics as sigma-2 (sigma2) selective ligands

5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2, 3-dimethoxybenzamide 1 is a potent and selective sigma2 receptor ligand suitable for further development. A series of new analogues, incorporating a variety of isoquinoline and carboxylic acid moieties, linked together with either a linear or cyclic amine spacer have been synthesised and assessed for their sigma1/sigma2 binding affinity and selectivity. Compounds with a rigid piperidine spacer gave Ki values for the sigma2 receptor between 8.7-845 nM. Changing the configuration of the methoxy groups on the isoquinoline moiety resulted in molecules with sigma2Ki values of 4.4-133 nM whereas varying the length and flexibility of the carbon spaces gave sigma2Ki values 0.88-15.0 nM, some of the most active, selective sigma2 ligands to date. Thus, the flexibility and length of the carbon linker and the carboxylic acid moiety are confirmed to be key to the exceptional binding affinity and selectivity for this active series. Additionally, the incorporation of a halogen on selected carboxylic acid moieties provided a convenient strategy for the introduction of a radiohalogen for applications in pharmacological and imaging studies.

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

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Oligo- and polymeric PdII and PtII using pyridyl carboxylate spacers for topology control

An array of PdII and PtII supramolecular assemblies have been constructed using pyridyl carboxylates as spacers and phosphines [(C5H4PPh2)2Fe (dppf) and PPh 3)] as supporting ligands. Different molecular topologies such as squares, triangles, rectangles, and polymers can be controlled by the spatial and directional character of the spacer. A change of the denticity of the phosphine does not affect the topological outcome. Significant differences, however, are observed for the congeneric analogues, with PdII showing a more pronounced tendency toward coordination polymer formation and its attached carboxyl a higher affinity toward Ag+. The ability of these assemblies to capture cations, such as Na+ in [Pt3Na(3- NC5H4CO2)3(OTf)3(PPh 3)6]+ through hydrogen bonding or Ag + in [PdAg(2-NC5H4CO2)(OTf) 2(dppf)] through dative bonding, is described and compared. All of the complexes are structurally characterized by single-crystal X-ray crystallography.

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

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Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization

An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.

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

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Redox-neutral alpha-oxygenation of amines: Reaction development and elucidation of the mechanism

Cyclic secondary amines and 2-hydroxybenzaldehydes or related ketones react to furnish benzo[e][1,3]oxazine structures in generally good yields. This overall redox-neutral amine alpha-C-H functionalization features a combined reductive N-alkylation/oxidative alpha-functionalization and is catalyzed by acetic acid. In contrast to previous reports, no external oxidants or metal catalysts are required. Reactions performed under modified conditions lead to an apparent reductive amination and the formation of o-hydroxybenzylamines in a process that involves the oxidation of a second equivalent of amine. A detailed computational study employing density functional theory compares different mechanistic pathways and is used to explain the observed experimental findings. Furthermore, these results also reveal the origin of the catalytic efficiency of acetic acid in these transformations.

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

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Novel metal chelators thiosemicarbazones with activity at the sigma2 receptors and P-glycoprotein: An innovative strategy for resistant tumor treatment

To combat the emergence of drug-resistance in tumors novel strategies are urgently needed. With this in mind we designed a novel class of thiosemicarbazones able to target simultaneously sigma2 receptors and P-glycoprotein efflux pump while chelating metals such as iron. The combined effect of these targets would lead to the activation of multiple pathways to which resistant tumors are sensitive. Indeed, most of the novel thiosemicarbazones displayed antiproliferative activity in both parent (MCF7 breast adenocarcinoma and A549 lung carcinoma) and corresponding doxorubicin-resistant cells (MCF7dx and A549dx). A few compounds emerged for their potent antiproliferative activity or for their more potent effect in doxorubicin-resistant cells than in the parent ones, while other compounds emerged for their remarkable P-gp modulatory activity. These results pave the way for further studies on these targets in the oncology field, while the availability of promising molecules for resistant tumors treatment that warrant deeper investigations was increased.

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

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Electrochemically initiated oxidative amination of benzoxazoles using tetraalkylammonium halides as redox catalysts

An electrochemically promoted coupling of benzoxazoles and amines has been developed, leading directly to the formation of 2-aminobenzoxazoles. The chemistry utilizes catalytic quantities of a tetraalkylammonium halide redox catalyst and is carried out under constant current conditions in a simple undivided cell. The use of excess chemical oxidant or large amounts of supporting electrolyte is avoided. This greatly simplifies the workup and isolation process and leads to a reduction in waste. (Chemical Equation Presented).

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

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Bioinspired organocatalytic aerobic C-H oxidation of amines with an ortho -quinone catalyst

A simple bioinspired ortho-quinone catalyst for the aerobic oxidative dehydrogenation of amines to imines is reported. Without any metal cocatalysts, the identified optimal ortho-quinone catalyst enables the oxidations of alpha-branched primary amines and cyclic secondary amines. Mechanistic studies have disclosed the origins of different performances of ortho-quinone vs para-quinone in biomimetic amine oxidations.

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

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QUINAZOLINE DERIVATIVES

Compounds of the formula I in which R, X, L2 and A1-A6 have the meanings indicated in Claim 1, are PI3K inhibitors and can be employed, inter alia, for the treatment of autoimmune diseases, inflammation, cardiovascular diseases, neurodegenerative diseases and tumours.

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

Awesome and Easy Science Experiments about 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

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Acylhydrazone as a novel “off-On-Off” fluorescence probe for the sequential detection of Al3+ and F-

A new acylhydrazone fluorescence probe, SPBH, was synthesized from salicylaldehyde and 4-(pyridin-4-yl)benzohydrazide (PBH). SPBH exhibited high selectivity and a sensitive fluorescence response towards Al3+, even in the presence of other competing metal ions in DMF/H2O (1:1, v/v) medium. And, the chemosensor can even detect Al3+ in the intracellular region of human non-small cell lung cancer H460 cells. The binding phenomenon of SPBH was investigated by 1H NMR spectroscopy and HR-MS. Mass spectrometry analysis showed a 1:1 complex formation of SPBH with Al3+. The Job plot also confirmed its 1:1 interaction. This SPBH/Al3+ complex exhibited excellent fluorescence “turn-off” properties towards the F- anion. Thus, SPBH acts as a sequential fluorescence “Off-On-Off” probe. The limits of detection for Al3+ and F- were calculated from the titration curve and found to be 1.1 ¡Á 10-7 M and 1.47 ¡Á 10-6 M, respectively.

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