Category: tetrahydroisoquinoline

The effect and mechanistic study of encequidar on reversing the resistance of SW620/AD300 cells to doxorubicin was written by Zhang, Hang;Bian, Shaopan;Xu, Zhihao;Gao, Ming;Wang, Han;Zhang, Junwei;Zhang, Mingkun;Ke, Yu;Wang, Weijia;Chen, Zhe-Sheng;Xu, Haiwei. And the article was included in Biochemical Pharmacology (Amsterdam, Netherlands) in 2022.Application In Synthesis of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

Encequidar, a gut-specific P-glycoprotein (P-gp) inhibitor, makes oral paclitaxel possible, and has been used in clin. treatment of metastatic breast cancer, however, its pharmacol. effect and mechanism of reversal of drug resistance in drug-resistant colon cancer cells SW620/AD300 are still unknown. Herein, we first synthesized encequidar and demonstrated that it could inhibit the transport activity of P-gp, reduced doxorubicin (DOX) efflux, enhanced DOX cytotoxicity and promoted tumor-apoptosis in SW620/AD300 cells. Metabolomic anal. of cell samples was performed using liquid chromatog. Q-Exactive mass spectrometer, the results of metabolite enrichment anal. and pathway anal. showed that the combination of encequidar and DOX could: i. significantly affect the citric acid cycle (TCA cycle) and reduce the energy supply required for P-gp to exert its transport activity; ii. affect the metabolism of glutathione, which is the main component of the anti-oxidative stress system, and reduce the ability of cells to resist oxidative stress; iii. increase the intracellular reactive oxygen species (ROS) production and enhance ROS-induced cell damage and lipid peroxidation, which in turn restore the sensitivity of drug-resistant cells to DOX. In conclusion, these results provide sufficient data support for the therapeutical application of the P-gp inhibitor encequidar to reverse MDR, and are of great significance to further understand the therapeutic advantages of encequidar in anti-tumor therapy and guide clin. rational drug use. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Application In Synthesis 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, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. 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.Application In Synthesis of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

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

Inhibiting Ferroptosis through Disrupting the NCOA4-FTH1 Interaction: A New Mechanism of Action was written by Fang, Yuying;Chen, Xiucai;Tan, Qingyun;Zhou, Huihao;Xu, Jun;Gu, Qiong. And the article was included in ACS Central Science in 2021.Safety of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

Ferroptosis is an iron-dependent form of oxidative cell death, and the inhibition of ferroptosis is a promising strategy with which to prevent and treat neurol. diseases. Herein we report a new ferroptosis inhibitor 9a(I) with a novel mechanism of action. It is demonstrated that nuclear receptor coactivator 4 (NCOA4), a cargo receptor for ferritinophagy, is the target of 9a. Compound 9a blocks ferroptosis by reducing the amount of bioavailable intracellular ferrous iron through disrupting the NCOA4-FTH1 protein-protein interaction. Further studies indicate that 9a directly binds to recombinant protein NCOA4^383-522 and effectively blocks the NCOA4^383-522-FTH1 interaction. In a rat model of ischemic stroke, 9a significantly ameliorates the ischemic-refusion injury. With the first ligand 9a, this work reveals that NCOA4 is a promising drug target. Addnl., 9a is the first NCOA4-FTH1 interaction inhibitor. This work paves a new road to the development of ferroptosis inhibitors against neurol. diseases. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Safety of 7-Methyl-1,2,3,4-tetrahydroisoquinoline).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. An intramolecular Friedel-Crafts cyclization of an in situ generated tosylate intermediate enables an efficient construction of 3-substituted 1,2,3,4-tetrahydroisoquinolines from N,N-dibenzyl-α-aminols.Safety of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

Iridium-Catalyzed Enantioselective α-C(sp³)-H Borylation of Azacycles was written by Chen, Lili;Yang, Yuhuan;Liu, Luhua;Gao, Qian;Xu, Senmiao. And the article was included in Journal of the American Chemical Society in 2020.Product Details of 207451-81-8 This article mentions the following:

Herein is reported an iridium-catalyzed enantioselective α-C(sp³)-H borylation of a wide range of azacycles. The combination of an iridium precursor and a chiral pyridyl 1,3,2-diazaborole bidentate boryl ligand has been shown to effectively differentiate enantiotopic methylene C-H bonds from a single carbon center, affording a variety of synthetically useful azacycles, e.g. I, from readily available starting materials with good to excellent enantioselectivities. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Product Details of 207451-81-8).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. Arene/Ru/TsDPEN complexes bearing a heterocyclic group catalyze the asymmetric transfer hydrogenation (ATH) of 1-aryl dihydroisoquinolines (DHIQs) to provide tetrahydroisoquinolines of high enantiomeric excess.Product Details of 207451-81-8

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

Chemoselective Strategy for the Direct Formation of Tetrahydro-2,5-methanobenzo[c]azepines or Azetotetrahydroisoquinolines via Regio- and Stereoselective Reactions was written by Kovacs, Ervin;Huszka, Balazs;Gati, Tamas;Nyerges, Miklos;Faigl, Ferenc;Mucsi, Zoltan. And the article was included in Journal of Organic Chemistry in 2019.Name: 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

The present study reports regio- and highly diastereoselective preparative methods for the synthesis of versatile alkaloid-type compounds from oxiranylmethyl tetrahydroisoquinolines. 2,5-Methanobenzo[c]azepines or azetidine-fused heterocycles were synthesized in tandem reactions depending on the absence or presence of a BF₃ co-reagent. A high functional group tolerance has also been demonstrated. DFT calculations with an explicit solvent model confirmed the proposed reaction mechanisms and the role of kinetic controls on the stereochem. outcome of the reported new methods. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Name: 7-Methyl-1,2,3,4-tetrahydroisoquinoline).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) 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. Arene/Ru/TsDPEN complexes bearing a heterocyclic group catalyze the asymmetric transfer hydrogenation (ATH) of 1-aryl dihydroisoquinolines (DHIQs) to provide tetrahydroisoquinolines of high enantiomeric excess.Name: 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

Scalable Process of Making 5,7-Dichloro-tetrahydroisoquinoline-6-carboxylic Acid Using Methylene as the Protecting Group was written by Xu, Wanbin;Gong, Xudong;Odilov, Abdullajon;Hu, Tianwen;Jiang, Xiangrui;Zhu, Fuqiang;Guo, Shuang;Jiang, Dehui;Wu, Mingjun;Shen, Jingshan. And the article was included in Organic Process Research & Development in 2021.HPLC of Formula: 73075-47-5 This article mentions the following:

The development of an industrially scalable synthetic route for a key starting material for Lifitegrast, compound I was described. The features of this route include: (1) Tetrahydroisoquinoline II was prepared by three steps from readily com. available 3, 5-dichlorobenzoyl chloride and 2-aminoethanol in a high total yield of 76%; (2) Formaldehyde instead of triphenylmethyl chloride was employed in the protection of the secondary amine, owning much higher atom economy; (3) The target compound I was produced with an overall yield of 66%, and an HPLC purity of 99% by area. In the experiment, the researchers used many compounds, for example, 5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 73075-47-5HPLC of Formula: 73075-47-5).

5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 73075-47-5) 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.HPLC of Formula: 73075-47-5

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

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination was written by Lu, Cong;Su, Zhishan;Jing, Dong;Jin, Songyang;Xie, Lijuan;Li, Liangrui;Zheng, Ke. And the article was included in Organic Letters in 2019.Product Details of 207451-81-8 This article mentions the following:

A visible-light-induced/thiourea-mediated intramol. cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivs I (R¹ = H, 9-Me, 9-F, 10-MeO, etc.; R² = H, 4-F, 4-Br, 3-F, 2-Me, etc.; R³ = H, (S)-5-Me, etc.). The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramol. single electron transfer (SET) is key stage in the catalytic cycle. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Product Details of 207451-81-8).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. 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.Product Details of 207451-81-8

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

Copper-catalyzed diastereoselective aerobic intramolecular dehydrogenative coupling of hydrazones via sp³ C-H functionalization was written by Wu, Xuesong;Wang, Mian;Zhang, Guangwu;Zhao, Yan;Wang, Jianyi;Ge, Haibo. And the article was included in Chemical Science in 2015.SDS of cas: 207451-81-8 This article mentions the following:

The highly diastereoselective intramol. dehydrogenative cyclization of N,N-disubstituted hydrazones via copper-catalyzed sp³ C-H bond functionalization process is described. The reaction protocol utilizes O₂ as the oxidant and shows great functional group compatibility. Computational studies suggest that a 5-center/6-electron disrotatory cyclization mechanism is probably involved in the process for controlling the diastereoselectivity. This work represents the first example of a copper-catalyzed, direct intramol. diastereoselective coupling reaction via an iminium ion intermediate. Addnl., it provides an environmentally friendly and atom efficient approach to access substituted pyrazolines, e.g, I, an important structural unit in many biol. active compounds In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8SDS of cas: 207451-81-8).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) 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.SDS of cas: 207451-81-8

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

Conopeptide-Derived κ-Opioid Agonists (Conorphins): Potent, Selective, and Metabolic Stable Dynorphin A Mimetics with Antinociceptive Properties was written by Brust, Andreas;Croker, Daniel E.;Colless, Barbara;Ragnarsson, Lotten;Andersson, Asa;Jain, Kapil;Garcia-Caraballo, Sonia;Castro, Joel;Brierley, Stuart M.;Alewood, Paul F.;Lewis, Richard J.. And the article was included in Journal of Medicinal Chemistry in 2016.Synthetic Route of C10H11NO2 This article mentions the following:

Opioid receptor screening of a conopeptide library led to a novel selective κ-opioid agonist peptide (conorphin T). Intensive medicinal chem., guided by potency, selectivity, and stability assays generated a pharmacophore model supporting rational design of highly potent and selective κ-opioid receptor (KOR) agonists (conorphins) with exceptional plasma stability. Conorphins are defined by a hydrophobic benzoprolyl moiety, a double arginine sequence, a spacer amino acid followed by a hydrophobic residue and a C-terminal vicinal disulfide moiety. The pharmacophore model was supported by computational docking studies, revealing receptor-ligand interactions similar to KOR agonist dynorphin A (1-8). A conorphin agonist inhibited colonic nociceptors in a mouse tissue model of chronic visceral hypersensitivity, suggesting the potential of KOR agonists for the treatment of chronic abdominal pain. This new conorphine KOR agonist class and pharmacophore model provide opportunities for future rational drug development and probes for exploring the role of the κ-opioid receptor. In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Synthetic Route of C10H11NO2).

(S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. 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.Synthetic Route of C10H11NO2

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

Electrochemical Approach for Direct C-H Phosphonylation of Unprotected Secondary Amine was written by Huang, Min;Dai, Jie;Cheng, Xu;Ding, Mengning. And the article was included in Organic Letters in 2019.Category: tetrahydroisoquinoline This article mentions the following:

Direct α-phosphonylation of an unprotected secondary amine in a single step is of practical importance to aminophosphates. However, this protocol is limited due to the high redox barrier of unprotected amine. The authors report C-H phosphonylation of an unprotected secondary amine via an electrochem. approach in the presence of catalytic carboxylate salt. This metal-free and exogenous oxidant-free method furnishes diverse target mols. with satisfactory yield under mild reaction conditions. Successful application of the protocol in a gram-scale experiment demonstrates the potential utility for further functionalization. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Category: tetrahydroisoquinoline).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. 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.Category: tetrahydroisoquinoline

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

Photocatalytic Approach for Construction of 5,6-Dihydroimidazo[2,1-a]isoquinolines and Their Luminescent Properties was written by Wang, Zaibin;Li, Hanjie;Wang, Zhichao;Suleman, Muhammad;Wang, Yanguang;Lu, Ping. And the article was included in Journal of Organic Chemistry in 2021.SDS of cas: 207451-81-8 This article mentions the following:

A visible-light-driven photoredox reaction of tetrahydroisoquinoline with 2H-azirines is described. 4,7-Bis(4-methoxyphenyl)benzo[c][1,2,5]thiadiazole, a benzothiadiazole (BTD) derived fluorophore, is used as an organic photoredox catalyst, and the reaction offers an efficient access to 5,6-dihydroimidazo[2,1-a]isoquinolines with a broad range of functional groups. The resulting 5,6-dihydroimidazo[2,1-a]isoquinolines present strong photoluminecence in solutions and powders and could be applied in the fabrication of blue OLED devices. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8SDS of cas: 207451-81-8).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. There has been increasing research interest and speculation since 1968 in the potential formation of tetrahydroisoquinoline (TIQ) alkaloids in mammalian cells via such interactions, and in the role such TIQs may have in alcohol dependence. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.SDS of cas: 207451-81-8

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