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

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Reactions of 6,7-dimethoxy- 3,4-dihydroisoquinoline with o-quinone methides

Products of heterocyclization, 9,10-dimethoxy-12,13-dihydro-7aH,15H- naphtho[1′,2′:5,6][1,3]oxazino-[2,3-a]isoquinolines, were isolated on condensing 6,7-dimethoxy-3,4-dihydroisoquinoline with 1-dimethylaminomethyl-2-naphthols. In the case of o-hydroxybenzyl alcohols products of a Michael aza reaction, 2-[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenols were obtained.

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

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THERMAL DECOMPOSITION OF 2-HYDROXYBENZYLAMINES

The results are given of the preparation of a number of 2-hydroxybenzylamines and their thermal decomposition.The thermolysis reactions and the formation of the corresponding amines take place smoothly and with good yields.

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

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Discovery of new potent dual sigma receptor/GluN2b ligands with antioxidant property as neuroprotective agents

Among several potential applications, sigma receptors (sigmaRs) can be used as neuroprotective agents, antiamnesic, antipsychotics and against other neurodegenerative disorders. On the other hands, antagonists of the GluN2b-subunit-containing-N-methyl-D-aspartate (NMDA) receptors are of major interest for the same purpose, being this subunit expressed in specific areas of the central nervous system and responsible for the excitatory regulation of nerve cells. Under these premises, we have synthesized and biologically tested novel hybrid derivatives obtained from the combination of phenyloxadiazolone and dihydroquinolinone scaffolds with different amine moieties, peculiar of sigma2R ligands. Most of the new ligands exhibited a pan-affinity towards both sigmaR subtypes and high affinity against GluN2b subunit. The most promising compounds belong to the dihydroquinolinone series, with the best affinity profile for the cyclohexylpiperazine derivative 28. Investigation on their biological activity showed that the new compounds were able to protect SH-SY5Y cells against oxidative stress induced by hydrogen peroxide treatment. These results proved that our dual sigmaR/GluN2b ligands have beneficial effects in a model of neuronal oxidative stress and can represent strong candidate pharmacotherapeutic agents for minimizing oxidative stress-induced neuronal injuries.

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

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Affinity of 2-(tetrahydroisoquinolin-2-methyl)- and 2-(isoindolin-2-ylmethyl)imidazolines for alpha-adrenoceptors. Differential affinity of imidazolines for the [3H]idazoxan-labeled alpha2-adrenoceptor vs the [3H]yohimbine-labeled site

A series of 2-(tetrahydroisoquinolin-2-ylmethyl)- and 2-(isoindolin-2-ylmethyl)imidazolines were prepared and tested for alpha1- and alpha2-adrenoceptor affinity with radioligand binding. Several compounds, 5-fluoro- (5h), 5-chloro- (5j), 5,8-dimethoxy- (5r), and 5,8-dimethoxy-1-methyl- (5s) 2-(tetrahydroisoquinolin-2-ylmethyl)imidazoline, were found to be selective alpha2-adrenoceptor ligands on the basis of displacement of [3H]yohimbine from rat cerebral cortical membranes. One compound, 2-[(8-chloro tetrahydroisoquinolin-2-yl)methyl]imidazoline (5m), showed a 36-fold difference in affinity for the [3H]idazoxan-labeled alpha2-adrenoceptor relative to the [3H]yohimbine-labeled site, which may be evidence for alpha2-adrenoceptor subtypes.

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

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Synthesis and evaluation of furoxan-based nitric oxide-releasing derivatives of tetrahydroisoquinoline as anticancer and multidrug resistance reversal agents

Multidrug resistance in tumor cells poses a major obstacle to efficient chemotherapy. Several types of agents have been recognized as multidrug resistance inhibitors, among which the tetrahydroisoquinolines is the most studied. In current study 16 furoxan-based nitric oxide-releasing derivatives of tetrahydroisoquinoline were synthesized. Their cytotoxic activities and effects in reversing multidrug resistance have been evaluated. The results revealed that these compounds had moderate cytotoxic effects. Compounds 7a-f, 7h, and 7l showed higher cytotoxicities than the rest, but lower than adriamycin on K562 cell line. Compounds 7d, 7f, and 7l exhibited potent MDR reversal activities on K562/A02 cell line. The accumulation assay indicated that compounds 7d, 7f, and 7l significantly increased the intracellular accumulation of rhodamine123 in K562/A02 cells. Furthermore, these three compounds produced high concentrations of NO in K562/A02 cells. Potentially, the high concentrations of NO produced by NO donor moieties will lead to an increased cytotoxicity to K562/A02 cells. Our results suggested that compounds 7d, 7f, and 7l had anticancer effects, as well as multidrug resistance reversal effects.

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

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Synthetic Route of 1745-07-9, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.1745-07-9, Name is 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline, molecular formula is C11H15NO2. In a article£¬once mentioned of 1745-07-9

Synthesis and SAR of novel capsazepine analogs with significant anti-cancer effects in multiple cancer types

We previously demonstrated that capsazepine (CPZ), a synthetic transient receptor potential Vanilloid subtype 1 (TRPV1) antagonist, has significant anti-cancer effects in vivo. The purpose of this study was to develop more potent analogs based upon CPZ pharmacophore and structure?activity relationships (SAR) across analogs. We generated 30 novel compounds and screened for their anti-proliferative effects in cultured HeLa cervical cancer cells. Cell viability assays identified multiple compounds with IC50s < 15 muM and one compound, 29 with an IC50 < 5 muM; six fold more potent than CPZ. We validated the anti-proliferative efficacy of two lead compounds, 17 and 29, in vivo using HeLa-derived xenografts in athymic nude mice. Both analogs significantly reduced tumor volumes by day 8 compared to control treated animals (p < 0.001) with no observable adverse effects. Calcium imaging determined that compound 17 activates TRPV1 whereas 29 neither activates nor inhibits TRPV1; indicating a unique mechanism-of-action that does not involve TRPV1 signaling. Cell viability assays using a panel of additional tumor types including oral squamous cell carcinoma, non-small cell lung cancer (NSCLC), breast cancer, and prostate cancer cell lines (HSC-3, H460, MDA-231, and PC-3 respectively) demonstrated that both lead compounds were efficacious against every cancer type tested. Compounds 29 displayed IC50s of 1?2.5 muM in HSC-3and PC-3cells. Thus, we propose that these novel CPZ analogs may serve as efficacious therapeutic agents against multiple tumor types that warrant further development for clinical application. A reaction mechanism is the microscopic path by which reactants are transformed into products. Each step is an elementary reaction. In my other articles, you can also check out more blogs about 1745-07-9 Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Final Thoughts on Chemistry for 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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CeO2-Catalyzed C-H Functionalization of N-Aryltetrahydroisoquinolines: An Aerobic Cross-Dehydrogenative Coupling Reaction between Two sp3 C-H Bonds

CeO2 has been used as heterogeneous catalyst for carbon-carbon bond formation via cross-dehydrogenative coupling (CDC). It works efficiently for oxidative C?C bond formation between N-aryltetrahydroisoquinoline derivatives and a carbon nucleophile nitroalkane and acetone under aerobic conditions. This is the first report of CeO2 as a low temperature catalyst for the carbon-carbon bond formation reaction between two sp3 C?H bonds.

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

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Search for anticonvulsant and analgesic active derivatives of dihydrofuran-2(3H)-one

A series of derivatives of dihydrofuran-2(3H)-one (gamma-butyrolactone, GBL) was synthesized and tested for anticonvulsant, neurotoxic and analgesic activity. In the anticonvulsant screening 10 lactones were effective in the maximal electroshock test (MES) at the highest doses (300 and 100 mg/kg, 0.5 h, ip, mice). Statistical analysis showed correlation between the anticonvulsant activity and relative lipophilicity parameters determined by experimental and computational methods (RM0, C log P and M log P). Preliminary antinociceptive evaluation of selected derivatives revealed strong analgesic activity. The majority of the tested compounds showed high efficacy in animal models of acute pain (hot plate and writhing tests) and strong local anesthetic activity (modified tail immersion test). The obtained ED50 values were comparable with such analgesics as acetylsalicylic acid and morphine.

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

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Diastereoselective alkylation of 2,3,4,6-Di-O-isopropylidene-2-keto-L-gulonic amides. Application to the asymmetric synthesis of 1-substituted-1,2,3,4-tetrahydroisoquinolines and 1-substituted-1,2,3,4,-tetrahydro-beta-carbolines

The diastereoselective alkylation of amides 3a,b and 7a,b derived from gulonic acid is described. Substituted compounds are obtained in good yield and high diastereoselectivity. A mechanistic investigation establishes that the diastereoselectivity did not arise from an initial asymmetric deprotonation. The stereochemistry is then determined during the alkylation step.

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

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

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Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air

Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing molecules with different conjugated systems indicated that both the oxygen-containing groups and large pi-conjugated system in GO sheets are essential for this reaction. (Figure presented.).

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