Chemical Properties and Facts of 7-Methoxy-1,2,3,4-tetrahydroisoquinoline

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Mitochondrial respiratory failure secondary to complex I inhibition may contribute to the neurodegenerative process underlying nigral cell death in Parkinson’s disease (PD). Isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) or 1-methyl-4-phenylpyridinium (MPP+) may be inhibitors of complex I, and have been implicated in the cause of PD as endogenous neurotoxins. To determine the potency and structural requirements of isoquinoline derivatives to inhibit mitochondrial function, we examined the effects of 22 neutral and quaternary compounds from three classes of isoquinoline derivatives (11 isoquinolines, 2 dihydroisoquinolines, and 9 1,2,3,4-tetrahydroisoquinolines) and MPP+ on the enzymes of the respiratory chain in mitochondrial fragments from rat forebrain. With the exception of norsalsolinol and N,n-propylisoquinolinium, all compounds inhibited complex I in a time-independent, but concentration-dependent manner, with IC50s ranging from 0.36-22 mM. Several isoquinoline derivatives were more potent inhibitors of complex I than 1-methyl-4-phenylpyridinium ion (MPP+) (IC50 = 4.1 mM), the most active being N-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline (IC50 = 0.36 mM) and 6-methoxy-1,2,3,4-tetrahydroisoquinoline (IC50 = 0.38 mM). 1,2,3,4-Tetrahydroisoquinoline was the least potent complex I inhibitor (IC50 ca. 22 mM). At 10 mM, only isoquinoline (23.1 percent), 6,7-dimethoxyisoquinoline (89.6 percent), and N-methylsalsolinol (34.8 percent) inhibited (P < 0.05) complex II-III, but none of the isoquinoline derivatives inhibited complex IV. There were no clear structure-activity relationships among the three classes of isoquinoline derivatives studied, but lipophilicity appears to be important for complex I inhibition. The effects of isoquinoline derivatives on mitochondrial function are similar to those of MPTP/MPP+, so respiratory inhibition may underlie their reported neurotoxicity. If you are interested in 43207-78-9, you can contact me at any time and look forward to more communication. Application In Synthesis of 7-Methoxy-1,2,3,4-tetrahydroisoquinoline

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

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A series of indolylcyclohexylamines possessing potent and selective serotonin reuptake inhibition is reported. The most interesting compounds proved to have subnanomolar 5-HT transporter activity, and exhibited moderate 5-HT1A affinity.

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

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Twenty new alkaloids, of which 13 are new natural products, have been discovered in Pachycereus weberi by tandem mass spectrometry using a mass-analyzed ion kinetic energy spectrometer.These observations have been confirmed by chromatography and, in many cases, by simple synthetic interconversions from known alkaloids.Particularly significant is the discovery of several alkaloids having the same molecular formula.Isomer distinctions such as these, which are difficult to make on pure compounds by mass spectrometry, were made by utilizing daughter spectra recorded succesively during the evaporation of the material from the probe and/or from spectra recorded on different types of plant extracts.This study suggests that many natural materials may contain trace amounts of compounds of potential biomedical or synthetic interest and, in particular, that the number of known alkaloids might be greatly increased by experiments of this type.

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

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Cyclic amines such as 1,2,3,4-tetrahydroisoquinoline undergo regiodivergent annulation reactions with 4-nitrobutyraldehydes. These redox-neutral transformations enable the asymmetric synthesis of highly substituted polycyclic ring systems in just two steps from commercial materials. The utility of this process is illustrated in a rapid synthesis of (-)-protoemetinol. Computational studies provide mechanistic insights and implicate the elimination of acetic acid from an ammonium nitronate intermediate as the rate-determining step.

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

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13C NMR ANALYSIS OF SOME SIMPLE TETRAHYDROISOQUINOLINES

13C NMR resonances of 15 simple tetrahydroisoquinolines have been assigned on the basis of chemical shift theory, 13C-1H coupling constants and deuterium labelling at specific positions.The chemical shifts of both aliphatic and aromatic protons were correlated with substituent effects. – Key Words : 13C NMR spectra; cactus alkaloids; simple tetrahydroisoquinolines; carnegine; heliamine; lemaireocereine; longimammatine; lophophorine; N-methylanhalinine; O-methylcorypalline; O-methyluberine; nortehuanine; tehuanine; weberidine.

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

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Synthesis and pharmacological evaluation of N-acyl-1,2,3,4- tetrahydroisoquinoline derivatives as novel specific bradycardic agents

A series of N-acyl-1,2,3,4-tetrahydroisoquinoline derivatives were synthesized and evaluated for their bradycardic activities in isolated guinea pig right atria and in urethane-anesthetized rats. These efforts resulted in identification of the compound 8a, which exhibits potent bradycardic activity with minimal influence on mean blood pressure in urethane-anesthetized rats. Oral administration of compound 8a to conscious rats revealed increased potency and prolonged duration of action when compared to Zatebradine.

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

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2 (OR 4) Amino 4 (or 2) N-hetero quinazolines

A series of novel 2-amino and 4-aminoquinazoline derivatives have been prepared, including their acid addition salts. These derivatives all possess a single nitrogen-containing benzo-fused heterocyclic ring moiety at either the 4- or 2- positions of the molecule, respectively, with the ring moiety being attached through the nitrogen atom to the aforesaid quinazoline nucleus. Such compounds are useful in therapy as highly potent antihypertensive agents. Methods for their preparation are described in detail, including various synthetic routes leading to the required novel intermediates.

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

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Discovery of novel tetrahydroisoquinoline derivatives as potent and selective factor Xa inhibitors

A series of novel 2,7-disubstituted tetrahydroisoquinoline derivatives were designed and synthesized. Among these derivatives, compounds 1 and 2 (JTV-803) exhibited potent inhibitory activity against FXa and good selectivity with respect to other serine proteases (thrombin, plasmin, and trypsin). In addition, compound 2 exhibited potent anti-FXa activity after intravenous and oral administration to cynomolgus monkey, and showed a dose-dependent antithrombotic effect in a rat model of venous thrombosis.

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

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DDQ-promoted mild and efficient metal-free oxidative alpha-cyanation of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines

A mild and highly efficient metal-free oxidative alpha-cyanation of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) has been accomplished at an ambient temperature via DDQ oxidation and subsequent trapping of N-acyl/sulfonyl iminium ions with (n-Bu)3SnCN. Employing readily removable N-acyl/sulfonyl groups as protecting groups rather than N-aryl ones enables a wide range of applications in natural product synthesis. The synthetic utility of the method was illustrated using a short and efficient formal total synthesis of (±)-calycotomine in three steps.

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

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Asymmetric Redox-Annulation of Cyclic Amines

Cyclic amines such as 1,2,3,4-tetrahydroisoquinoline undergo regiodivergent annulation reactions with 4-nitrobutyraldehydes. These redox-neutral transformations enable the asymmetric synthesis of highly substituted polycyclic ring systems in just two steps from commercial materials. The utility of this process is illustrated in a rapid synthesis of (-)-protoemetinol. Computational studies provide mechanistic insights and implicate the elimination of acetic acid from an ammonium nitronate intermediate as the rate-determining step.

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