Category: 2328-12-3

Chemical modification of tetrahydroisoquinoline and their cytotoxic activity was written by Terenteva, Ekaterina O.;Khashimova, Zaynat S.;Tsay, Elena A.;Zhurakulov, Sherzod N.;Saidov, Abdusalom Sh.;Vinogradova, Valentina I.;Azimova, Shakhnoz S.. And the article was included in Asian Journal of Pharmacy and Pharmacology in 2017.Electric Literature of C11H16ClNO2 This article mentions the following:

A variety of differently functionalized 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines I [R = H, Me, CH₂CH₂OH; R¹ = H, Ph, 1,3-benzodioxol-5-yl, etc.], bis tetrahydroisoquinolines II [X = (CH₂)₄, 1,3-phenylene, (CH₂)₁₁, etc.; R² = MeO, R²R² = OCH₂O] and chromanones III [R³ = 2-(1,3-benzodioxol-5-yl)ethylamino, 2-(3,4-dimethoxyphenyl)ethylamino, 6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl, etc.] were synthesized. Classic intramol. Bischler-Napieralski cyclodehydration was employed to generate the isoquinoline core. All the structures were characterized by NMR and mass spectrometry. The cytotoxic activities against three human cancer cell lines and primary culture of healthy hepatocyte cells were evaluated for all the synthesized compounds and structure-activity relationships were established by MTT assay. It was shown that compound I [R = H, R¹ = hexyl] was demonstrated selective cytotoxicity against breast adenocarcinoma (IC₅₀: 43.3 μM), I [R = H, R¹ = 6-chloro-1,3-benzodioxol-5-yl; R = Me, R¹ = 1,3-benzodioxol-5-yl] against laryngeal adenocarcinoma (IC₅₀: 18.0 and 2.3 μM resp.) with the absence of toxicity to healthy cells. Bis compounds II exhibited greater cytotoxic effect than mono-series compounds I. Among bis samples compound II [X = (CH₂)₁₁, R² = MeO] showed the greatest cytotoxic properties with an IC₅₀ value of 3.1-4.0 μM. The all conjugate compounds completely lacked cytotoxicity toward cancer cell lines and III [R³ = 2-(1,3-benzodioxol-5-yl)ethylamino, 6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl] demonstrated proliferative activity. The most promising compounds for further study in-vitro and in-vivo methods were dibasic compounds II [X = (CH₂)₇, (CH₂)₈; R² = MeO]. Later these substances can be offered as a basis for drugs with anti-tumor properties. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Electric Literature of C11H16ClNO2).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.Electric Literature of C11H16ClNO2

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

Synthesis and evaluation of pyrimidoindole analogs in umbilical cord blood ex-vivo expansion was written by Feng, Yue;Xie, Xiao-Yang;Yang, Yi-Qiu;Sun, Yu-Tong;Ma, Wen-Hui;Zhou, Peng-Jun;Li, Zi-Yao;Liu, Hui-Qiang;Wang, Yi-Fei;Huang, Yun-Sheng. And the article was included in European Journal of Medicinal Chemistry in 2019.Synthetic Route of C11H16ClNO2 This article mentions the following:

The synthesis of pyrimidoindole analogs I [R = dimethylamino, 3-chloro-4-fluoroanilino, 3,4-dimethoxyphenthylamino, etc.] and II [R¹ = anilino, morpholino, indole-3-ethylamino, etc.] and identified 6 compounds to be potent in promoting HSC ex vivo expansion. In particular, analog I [R = 2-(6,7-dimethoxy-1,2,3,4-trtrahydroisoquinolino)ethylamino (III)] was found to be the most effective in stimulating ex-vivo expansion of UCB CD34⁺ cells and CD34⁺CD38^– cells. Initial data indicated that compound III promoted the absolute number of long term HSCs and inhibited their differentiation. UCB HSCs expanded with III retained adequate multi-lineage differentiation capacity. In addition, compound III was not cytotoxic at its test concentrations, suggested that it merits further investigation for potential clin. applications. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Synthetic Route of C11H16ClNO2).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.Synthetic Route of C11H16ClNO2

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

The Discovery of Capsazepine, the First Competitive Antagonist of the Sensory Neuron Excitants Capsaicin and Resiniferatoxin was written by Walpole, Christopher S. J.;Bevan, Stuart;Bovermann, Guenter;Boelsterli, Johann J.;Breckenridge, Robin;Davies, John W.;Hughes, Glyn A.;James, Iain;Oberer, Lukas. And the article was included in Journal of Medicinal Chemistry in 1994.Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

Capsaicin and resiniferatoxin are natural products which act specifically on a subset of primary afferent sensory neurons to open a novel cation-selective ion channel in the plasma membrane. Conformationally constrained analogs I [R¹ = OH, OMe, H; R² = OH, OMe; R³ = H, OH; R⁴ = octyl, 4-ClC₆H₄CH₂CH₂; n = 1-3] of these mols. were prepared The resulting compounds provided agonists of comparable potency to unconstrained analogs as well as a moderately potent antagonist, capsazepine (I, R¹ = R² = OH, R³ = H, R⁴ = 4-ClC₆H₄CH₂CH₂, n = 3). This compound is the first competitive antagonist of capsaicin and resiniferatoxin to be described and is active in various systems, in vitro and in vivo. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

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

Visible Light-Driven α-Alkylation of N-Aryl tetrahydroisoquinolines Initiated by Electron Donor-Acceptor Complexes was written by Xia, Qing;Li, Yufei;Wang, Xinmin;Dai, Peng;Deng, Hongping;Zhang, Wei-Hua. And the article was included in Organic Letters in 2020.Electric Literature of C11H16ClNO2 This article mentions the following:

The visible light-driven α-alkylation of N-aryl tetrahydroisoquinolines was initiated through electron donor-acceptor complex photochem. The reaction can proceed smoothly without the addition of any photocatalysts, transition-metal catalysts, or addnl. oxidants. The proposed mechanism was supported by various mechanistic studies, and the reactive open-shell alkyl radicals were generally produced from an alkylamine and underwent radical coupling for alkylating a wide range of N-aryl tetrahydroisoquinolines. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Electric Literature of C11H16ClNO2).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This is no longer generally accepted by the scientific community.Electric Literature of C11H16ClNO2

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

Design, synthesis and evaluation of novel triazole core based P-glycoprotein-mediated multidrug resistance reversal agents was written by Jiao, Lei;Qiu, Qianqian;Liu, Baomin;Zhao, Tianxiao;Huang, Wenlong;Qian, Hai. And the article was included in Bioorganic & Medicinal Chemistry in 2014.Recommanded Product: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

A novel series of triazol-N-ethyl-tetrahydroisoquinoline based compounds were designed and synthesized via click chem. Most of the synthesized compounds showed P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) reversal activities. Among them, compound 7 with little cytotoxicity towards GES-1 cells (IC₅₀ >80 μM) and K562/A02 cells (IC₅₀ >80 μM) exhibited more potency than verapamil (VRP) on increasing anticancer drug accumulation in K562/A02 cells. Moreover, compound 7 could significantly reverse MDR in a dose-dependent manner and also persist longer chemo-sensitizing effect than VRP with reversibility. Further mechanism studies revealed that compound 7 in reversing MDR revealed that it could remarkably increase the intracellular accumulation of both rhodamine-123 (Rh123) and adriamycin (ADM) in K562/A02 cells as well as inhibit their efflux from the cells. These results suggested that compound 7 showed more potency than the classical P-gp inhibitor VRP under the same conditions, which may be a promising P-gp-mediated MDR modulator for further development. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Recommanded Product: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.Recommanded Product: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

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

Synthesis and in vitro evaluation of tetrahydroisoquinolinyl benzamides as ligands for σ receptors was written by Xu, Rong;Lever, John R.;Lever, Susan Z.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Category: tetrahydroisoquinoline This article mentions the following:

5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2,3-dimethoxy-benzamide (I) is one of the most potent and selective σ ₂ receptor ligands reported to date. Previous structure-activity relationship studies of such tetrahydroisoquinolinyl benzamides have focused on the linker that connects the ring systems and the effects of benzamide ring substituents. The present study explores the effects of fusing methylene-, ethylene-, and propylenedioxy rings onto the tetrahydroisoquinoline in place of the two methoxy groups. These modifications decreased σ₂ affinity by 8- to 12-fold, with no major differences noted with ring size. By contrast, the methylenedioxy analog showed a 10-fold greater σ₁ affinity than I, and progressively lower σ₁ affinities were then noted with increasing ring size. The tetrahydroisoquinoline ring of I was opened to study the effects of greater conformational fluidity on σ receptor binding. The σ₂ affinity of the open-ring compound decreased by 1700-fold, while σ₁ affinity was not changed. Thus, a constrained tetrahydroisoquinoline ring system is key to the exceptional σ₂ receptor binding affinity and selectivity of this active series. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Category: tetrahydroisoquinoline).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. Because of the high biological relevance of compounds possessing the 1,2,3,4-tetrahydroisoquinoline framework, a large number of synthetic approaches towards the creation of an isoquinoline or 1,2,3,4-tetrahydroisoquinoline core are presently known. However, synthetic routes to tetrahydroisoquinoline derivatives containing fluorine atom(s) in their structure are not particularly abundant.Category: tetrahydroisoquinoline

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

Ring-opening reactions of halogenated N-aryl-1,2,3,4-tetrahydroisoquinoline and 2,3,4,5-tetrahydro-1H-2-benzazepine derivatives was written by Stanley, Alan L.;Stanforth, Stephen P.. And the article was included in Journal of Heterocyclic Chemistry in 1995.Recommanded Product: 2328-12-3 This article mentions the following:

Title compounds I [n = 1, 2; R = H, OMe; R¹ = C₆F₅, tetrafluoropyrid-4-yl, C₆Cl₅] were prepared and their ring-opening reactions with N-bromosuccinimide investigated. I [n = 1, R = H, OMe, R¹ = C₆F₅] gave a mixture of products which did not contain any significant quantity of the aldehydes II whereas the other I gave II exclusively. Compound 10 similarly gave the aldehyde 11 when treated with NBS. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Recommanded Product: 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is present in a number of drugs, such as tubocurarine, one of the quaternary ammonium muscle relaxants. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.Recommanded Product: 2328-12-3

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

Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters was written by Orjales, Aurelio;Mosquera, Ramon;Toledo, Antonio;Pumar, M. Carmen;Garcia, Neftali;Cortizo, Lourdes;Labeaga, Luis;Innerarity, Ana. And the article was included in Journal of Medicinal Chemistry in 2003.Recommanded Product: 2328-12-3 This article mentions the following:

In a wide search program toward new, efficient, and fast-acting antidepressant drugs, series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane) were prepared These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT_1A and 5-HT_2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidines I (R¹ = H, Me, MeCO; R² = H, 3-F, 4-F, 4-Cl, 4-Me; R³ = H, 2-CN, 4-O₂N, 4-MeO, 2-Ph, etc.) showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT_1A and 5-HT_2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α₂ receptor. Several of these enantiomers, (-)-I (R¹ = R² = H; R³ = 2-F), (-)-I (R¹ = R² = H; R³ = 3-F), (-)-I (R¹ = H; R² = 3-F; R³ = 2-F), (+)-I (R¹ = H; R² = R³ = 3-F), displayed a dual binding profile with affinities for SERT and NET with K_i < 25 nM and a NET/SERT ratio <10. (-)-I (R¹ = R² = H; R³ = 3-F) (coded as F-98214-TA for development studies) showed a dual binding profile with very high affinity values for SERT and NET (K_i = 1.9 and 13.5 nM, resp.), and further pharmacol. characterization is in progress for its evaluation as a antidepressant. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Recommanded Product: 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. An efficient CuCl2-catalyzed coupling of nonfunctionalized tetrahydroisoquinolines with organozinc reagents under aerobic conditions proceeds in high yields under mild reaction conditions and is broadly applicable to a wide range of substrates. The reaction involves an iminium ion intermediate that is formed via a SET process.Recommanded Product: 2328-12-3

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

Discovery of aromatic amides with triazole-core as potent reversal agents against P-glycoprotein-mediated multidrug resistance was written by Qiu, Qianqian;Zhu, Jilan;Chen, Qiutong;Jiang, Ziqian;Xu, Jiting;Jiang, Xueting;Huang, Wenlong;Liu, Zhongquan;Ye, Jing;Xu, Xiaojuan. And the article was included in Bioorganic Chemistry in 2019.Quality Control of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a major impediment for clin. cancer therapy. 19 novel aromatic amides with triazole-core as MDR reversal agents were designed and synthesized via click chem. to reverse MDR. Among them, compound 42 was identified as the most promising candidate with high potency (EC₅₀ = 78.1 ± 5.4 nM), low cytotoxity (SI > 1282) and persistent duration in reversing doxorubicin (DOX) resistance in K562/A02 cells. 42 also enhanced the potency of other P-gp associated cytotoxic agents with different structures. In further study, remarkably increased intracellular accumulation of Rh123 and DOX in K562/A02 cells was achieved by compound 42, while CYP3A4 activity had no change by compound 42. These results indicate that compound 42 as a relatively safe modulator of P-gp-mediated MDR has good potential for further development. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Quality Control of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.Quality Control of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

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

Topological pattern for the search of new active drugs against methicillin resistant Staphylococcus aureus was written by Bueso-Bordils, Jose I.;Perez-Gracia, Maria T.;Suay-Garcia, Beatriz;Duart, Maria J.;Martin Algarra, Rafael V.;Lahuerta Zamora, Luis;Anton-Fos, Gerardo M.;Aleman Lopez, Pedro A.. And the article was included in European Journal of Medicinal Chemistry in 2017.SDS of cas: 2328-12-3 This article mentions the following:

Mol. topol. was used to develop a math. model capable of classifying compounds according to antimicrobial activity against methicillin resistant Staphylococcus aureus (MRSA). Topol. indexes were used as structural descriptors and their relation to antimicrobial activity was determined by using linear discriminant anal. This topol. model establishes new structure activity relationships which show that the presence of cyclopropyl, chlorine and ramification pairs at a distance of two bonds favor this activity, while the presence of tertiary amines decreases it. This model was applied to a combinatorial library of a thousand and one 6-fluoroquinolones, from which 117 theor. active mols. were obtained. The compound 10 and five new quinolones were tested against MRSA. They all showed some activity against MRSA, although compounds 6, 8 and 9 showed anti-MRSA activity similar to ciprofloxacin. This model was also applied to 263 theor. antibacterial agents described by the authors in a previous work, from which 34 were predicted as theor. active. Anti-MRSA activity was found bibliog. in 9 of them (ensuring at least 26% of success), and from the rest, 3 compounds were randomly chosen and tested, finding mitomycin C to be more active than ciprofloxacin. The results demonstrate the utility of the mol. topol. approaches for identifying new drugs active against MRSA. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3SDS of cas: 2328-12-3).

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This is no longer generally accepted by the scientific community.SDS of cas: 2328-12-3

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