Month: December 2022

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

Comparative molecular field analysis (CoMFA) models of phenylethanolamine N-methyltransferase (PNMT) and the α₂-adrenoceptor: the development of new, highly selective inhibitors of PNMT was written by Grunewald, Gary L.;Caldwell, Timothy M.;Dahanukar, Vilas H.;Jalluri, Ravi K.;Criscione, Kevin R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1999.Application of 207451-81-8 This article mentions the following:

As a guide to the development of new and more selective inhibitors of phenylethanolamine N-methyltransferase (PNMT) vs. the α₂-adrenoceptor, we have performed a comparative mol. field anal. (CoMFA) on a series of 80 benzylamine analogs. Using the models obtained, we have proposed a series of 3-trifluoromethyl-1,2,3,4-tetrahydroisoquinolines and predicted the activity of other analogs. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Application 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. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. 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.Application of 207451-81-8

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

Cu^II/TEMPO-Catalyzed Enantioselective C(sp³)-H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation was written by Gao, Pei-Sen;Weng, Xin-Jun;Wang, Zhen-Hua;Zheng, Chao;Sun, Bing;Chen, Zhi-Hao;You, Shu-Li;Mei, Tian-Sheng. And the article was included in Angewandte Chemie, International Edition in 2020.Application of 207451-81-8 This article mentions the following:

A novel strategy for asym. Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochem., affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Application of 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. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.Application of 207451-81-8

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

High-performance liquid chromatographic separation of enantiomers of synthetic amino acids on a ristocetin A chiral stationary phase was written by Peter, A.;Torok, G.;Armstrong, D. W.;Toth, G.;Tourwe, D.. And the article was included in Journal of Chromatography A in 2000.Computed Properties of C10H11NO2 This article mentions the following:

A macrocyclic glycopeptide, ristocetin A, was used as chiral stationary phase for the HPLC separation of enantiomers of 28 unnatural amino acids, such as analogs of phenylalanine, tyrosine and tryptophan, and analogs containing 1,2,3,4-tetrahydroisoquinoline, tetraline or 1,2,3,4-tetrahydro-2-carboline skeletons. Excellent resolutions were achieved for most of the studied compounds by using reversed-phase or a new polar-organic mobile phase system. The conditions of separation were optimized by variation of the mobile phase composition, temperature and flow-rate. In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Computed Properties of C10H11NO2).

(S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is present in a number of drugs, such as tubocurarine, one of the quaternary ammonium muscle relaxants. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.Computed Properties of C10H11NO2

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

Chromatographic methods for monitoring the optical isomers of unusual aromatic amino acids was written by Peter, Antal;Torok, Gabriella;Toth, Geza;Van Den Nest, Wim;Georges Laus;Tourwe, Dirk. And the article was included in Journal of Chromatography A in 1998.Application of 151004-92-1 This article mentions the following:

Unusual aromatic amino acids (phenylalanine, tyrosine and tryptophan analogs, and analogs containing tetraline, 1,2,3,4-tetrahydroisoquinoline or 1,2,3,4-tetrahydro-2-carboline skeletons) were synthesized in racemic or chiral form. The enantiomers of these unusual aromatic amino acids were separated by different chromatog. methods. The gas chromatog. analyses were based on separation on a Chirasil-L-Val column, using N-trifluoroacetyl-iso-Bu esters of amino acids, while HPLC was carried out either on a Crownpak CR(+) chiral column, or on an achiral column for the separation of diastereomeric derivatives formed with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide or 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate. In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Application of 151004-92-1).

(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. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. 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.Application of 151004-92-1

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

Directed (R)- or (S)-selective dynamic kinetic enzymatic hydrolysis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic esters was written by Paal, Tihamer A.;Liljeblad, Arto;Kanerva, Liisa T.;Forro, Eniko;Fulop, Ferenc. And the article was included in European Journal of Organic Chemistry in 2008.Computed Properties of C10H11NO2 This article mentions the following:

The first synthesis of both enantiomers of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (I) was accomplished through dynamic kinetic resolution in procedures based on CAL-B- or subtilisin Carlsberg-catalyzed enantioselective hydrolysis of the corresponding Et esters in aqueous NH₄OAc buffer at pH 8.5. The products were obtained with high enantiopurity (92-93% ee) in good yields (85-92%). (R)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (II) was obtained with high enantiopurity (98% ee) and in good yield (85%) in a CAL-B-catalyzed process, under similar conditions. In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Computed Properties 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. Among them, 1-substituted tetrahydroisoquinolines are privileged scaffolds in drugs and pharmaceuticals. 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.Computed Properties of C10H11NO2

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

Prediction of enantiomeric selectivity in chromatography. Application of conformation-dependent and conformation-independent descriptors of molecular chirality was written by Aires-de-Sousa, Joao;Gasteiger, Johann. And the article was included in Journal of Molecular Graphics & Modelling in 2002.HPLC of Formula: 151004-92-1 This article mentions the following:

To process mol. chirality by computational methods and to obtain predictions for properties that are influenced by chirality, a fixed-length conformation-dependent chirality code is introduced. The code consists of a set of mol. descriptors representing the chirality of a 3-dimensional mol. structure. It includes information about mol. geometry and at. properties, and can distinguish between enantiomers, even if chirality does not result from chiral centers. The new mol. transform was applied to two datasets of chiral compounds, each of them containing pairs of enantiomers that had been separated by chiral chromatog. The elution order within each pair of isomers was predicted by Kohonen neural networks (NN) using the chirality codes as input. A previously described conformation-independent chirality code was also applied and the results were compared. In both applications clustering of the two classes of enantiomers (first eluted and last eluted enantiomers) could be successfully achieved by NN and accurate predictions could be obtained for independent test sets. The chirality code described here has a potential for a broad range of applications from stereoselective reactions to anal. chem. and to the study of biol. activity of chiral compounds In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1HPLC of Formula: 151004-92-1).

(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. Among them, 1-substituted tetrahydroisoquinolines are privileged scaffolds in drugs and pharmaceuticals. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.HPLC of Formula: 151004-92-1

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

High-performance liquid chromatographic separation of enantiomers of unusual amino acids on a teicoplanin chiral stationary phase was written by Peter, Antal;Torok, Gabriella;Armstrong, Daniel W.. And the article was included in Journal of Chromatography A in 1998.Synthetic Route of C10H11NO2 This article mentions the following:

A glycopeptide antibiotic, teicoplanin, was used as chiral stationary phase for the HPLC separation of enantiomers of >30 unnatural amino acids, such as phenylalanine and tyrosine analogs and analogs containing 1,2,3,4-tetrahydroisoquinoline, tetraline, 1,2,3,4-tetrahydro-2-carboline, cyclopentane, cyclohexane, cyclohexene, bicyclo[2.2.1]heptane or heptene skeletons. Excellent resolutions were achieved for most of the studied compounds by using a hydro-organic mobile-phase system. The effects of organic modifier content, temperature and flow-rate on the resolution were studied and the conditions of separation were optimized. 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 can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. 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.Synthetic Route of C10H11NO2

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

Synthesis of 3-aryl-3-benzazepines via aryne [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines was written by Pan, Xuan;Liu, Zhanzhu. And the article was included in Organic Chemistry Frontiers in 2018.Safety of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

An efficient method for the synthesis of 3-aryl-3-benzazepines via aryne induced [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines was described. This approach provided straightforward access to 3-aryl-3-benzazepines in moderate to good yields under transition-metal-free and strong-base-free conditions. Temperature-dependent α-arylated products of the carbonyl group were also obtained. Preliminary mechanistic studies suggest both 3-aryl-3-benzazepines and α-arylated products of the carbonyl group were generated via the rearrangement of nitrogen ylide intermediates. 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 motif is often present in natural products with a broad range of biological and pharmacological activities. 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.Safety of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

Chemoenzymatic Approach to (S)-1,2,3,4-Tetrahydroisoquinoline Carboxylic Acids Employing D-Amino Acid Oxidase was written by Ju, Shuyun;Qian, Mingxin;Xu, Gang;Yang, Lirong;Wu, Jianping. And the article was included in Advanced Synthesis & Catalysis in 2019.Synthetic Route of C10H11NO2 This article mentions the following:

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4-tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was exploited through genome mining, and applied for the kinetic resolution of a number of racemic 1- and 3-carboxyl substituted tetrahydroisoquinolines to yield the corresponding (S)-enantiomers with excellent enantiomeric excess (ee) values (up to >99%). By using FsDAAO in combination with ammonia-borane in one pot, deracemization of these racemic carboxyl-substituted tetrahydroisoquinolines was achieved with conversions up to >98% and >99% ee. Preparative-scale deracemization of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was also demonstrated with good isolated yields (82% and 73%, resp.) and ee>99%. Our study provides an effective method for the synthesis of enantiomeric pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids. This method is expected to provide access to chiral carboxyl-substituted 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-ss-carbolines. 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. Among them, 1-substituted tetrahydroisoquinolines are privileged scaffolds in drugs and pharmaceuticals. 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.Synthetic Route of C10H11NO2

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