Month: October 2022

Safety of 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidOn June 12, 2014, Kathman, Stefan G.; Xu, Ziyang; Statsyuk, Alexander V. published an article in Journal of Medicinal Chemistry. The article was 《A Fragment-Based Method to Discover Irreversible Covalent Inhibitors of Cysteine Proteases》. The article mentions the following:

A novel fragment-based drug discovery approach is reported which irreversibly tethers drug-like fragments to catalytic cysteines. Acrylamides, acylaminoacrylates, vinylsulfonamides, and acylaminopropenyl sulfones were prepared and the dependence of their rates of reaction with N-acetylcysteine Me ester on their structure was determined; of the compounds tested, the rate of Michael addition of N-acetylcysteine Me ester to acylaminoacrylates depended least on the acyl moiety. A library of 100 fragment-substituted acylaminoacrylates was prepared; addition of subsets of the library to papain followed by mass spectrometric anal. identified three acylaminoacrylates which selectively reacted with the cysteine protease papain. The kinetics of the inhibition of papain by the acylaminoacrylates, the effect of known inhibitors of papain on its inhibition by the acylaminoacrylates, and the lack of inhibition of other cysteine proteases (human rhinovirus 3C protease, the catalytic domain of the deubiquitinase USP08, and the E2 ubiquitin-conjugating enzyme UbcH7) by the acylaminoacrylates supported their identification as selective and irreversible papain inhibitors. In the experiment, the researchers used 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 54329-54-3Safety of 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 54329-54-3) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Safety of 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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

In 1968,Chemical & Pharmaceutical Bulletin included an article by Tachibana, Shinro; Matsuo, Hisayuki; Yamada, Shunichi. SDS of cas: 54329-54-3. The article was titled 《Chemistry of amino acids. IV. Decarboxylation of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives》. The information in the text is summarized as follows:

Decarboxylation of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives, I, II, III, IV and IV.HCl, in acetophenone and BzH solvents, was examined In the case of IV.HCl, 4-substituted isoquinoline derivatives were formed in moderate yield according to the solvent used. 25 references. After reading the article, we found that the author used 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 54329-54-3SDS of cas: 54329-54-3)

2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 54329-54-3) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.SDS of cas: 54329-54-3 It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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

Recommanded Product: 799274-06-9On September 13, 2012 ,《3-(3,4-Dihydroisoquinolin-2(1H)-ylsulfonyl)benzoic Acids: Highly Potent and Selective Inhibitors of the Type 5 17-β-Hydroxysteroid Dehydrogenase AKR1C3》 was published in Journal of Medicinal Chemistry. The article was written by Jamieson, Stephen M. F.; Brooke, Darby G.; Heinrich, Daniel; Atwell, Graham J.; Silva, Shevan; Hamilton, Emma J.; Turnbull, Andrew P.; Rigoreau, Laurent J. M.; Trivier, Elisabeth; Soudy, Christelle; Samlal, Sharon S.; Owen, Paul J.; Schroeder, Ewald; Raynham, Tony; Flanagan, Jack U.; Denny, William A.. The article contains the following contents:

A high-throughput screen identified 3-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)benzoic acid as a novel, highly potent (low nM), and isoform-selective (1500-fold) inhibitor of aldo-keto reductase AKR1C3: a target of interest in both breast and prostate cancer. Crystal structure studies showed that the carboxylate group occupies the oxyanion hole in the enzyme, while the sulfonamide provides the correct twist to allow the dihydroisoquinoline to bind in an adjacent hydrophobic pocket. SAR studies around this lead showed that the positioning of the carboxylate was critical, although it could be substituted by acid isosteres and amides. Small substituents on the dihydroisoquinoline gave improvements in potency. A set of “”reverse sulfonamides””, e.g., I (R = CO2H, R1 = H; R = H, R1 = CO2H), showed a 12-fold preference for the R stereoisomer. The compounds showed good cellular potency, as measured by inhibition of AKR1C3 metabolism of a known dinitrobenzamide substrate, with a broad rank order between enzymic and cellular activity; but amide analogs were more effective than predicted by the cellular assay. In addition to this study using 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride, there are many other studies that have used 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9Recommanded Product: 799274-06-9) was used in this study.

7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: 799274-06-9 It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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

Albers, Harald M. H. G.; Hendrickx, Loes J. D.; van Tol, Rob J. P.; Hausmann, Jens; Perrakis, Anastassis; Ovaa, Huib published an article in Journal of Medicinal Chemistry. The title of the article was 《Structure-Based Design of Novel Boronic Acid-Based Inhibitors of Autotaxin》.Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The author mentioned the following in the article:

Autotaxin (ATX) is a secreted phosphodiesterase that hydrolyzes the abundant phospholipid lysophosphatidylcholine (LPC) to produce lysophosphatidic acid (LPA). The ATX-LPA signaling axis has been implicated in inflammation, fibrosis, and tumor progression, rendering ATX an attractive drug target. We recently described a boronic acid-based inhibitor of ATX, named HA155 (1). Here, we report the design of new inhibitors based on the crystal structure of ATX in complex with inhibitor 1. Furthermore, we describe the syntheses and activities of these new inhibitors, whose potencies can be explained by structural data. To understand the difference in activity between two different isomers with nanomolar potencies, we performed mol. docking experiments Intriguingly, mol. docking suggested a remarkable binding pose for one of the isomers, which differs from the original binding pose of inhibitor 1 for ATX, opening further options for inhibitor design. In the part of experimental materials, we found many familiar compounds, such as (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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

Name: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidOn October 31, 1998 ,《A rapid, qualitative thin-layer chromatographic method for the separation of the enantiomers of unusual aromatic amino acids》 appeared in Journal of Planar Chromatography–Modern TLC. The author of the article were Darula, Zsuzsanna; Torok, Gabriella; Wittmann, Gyula; Mannekens, Els; Iterbeke, Koen; Toth, Geza; Tourwe, Dirk; Peter, Antal. The article conveys some information:

A rapid thin-layer chromatog. (TLC) method was developed for the separation and purity control of the enantiomers of several unusual aromatic amino acids (phenylalanine, tyrosine, histidine, and tryptophan analogs, and analogs containing tetralin or 1,2,3,4-tetrahydroisoquinoline skeletons) synthesized in racemic or homochiral form. The compounds were analyzed on Macherey-Nagel Chiralplate TLC plates with acetonitrile-methanol-water, 4 + 1 + 1 or 4 + 1 + 2 (volume/volume) or acetonitrile-methanol-water-diisopropylethylamine, 4 + 1 + 2 + 0.1 (volume/volume) as mobile phase. The compounds were visualized with ninhydrin. Good separation and reliable results were usually obtained. The configurations of the asym. centers of the studied amino acids were determined either using enantiomerically pure amino acids as standards or using enzymes, e.g. α-chymotrypsin, L-amino acid oxidase or carboxypeptidase A. By this method the configurations of unnatural amino acids built into peptides can also be determined after hydrolysis of the peptides. The experimental part of the paper was very detailed, including the reaction process of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Name: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Name: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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

Reference of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidOn March 31, 2002, Aires-de-Sousa, Joao; Gasteiger, Johann published an article in Journal of Molecular Graphics & Modelling. The article was 《Prediction of enantiomeric selectivity in chromatography. Application of conformation-dependent and conformation-independent descriptors of molecular chirality》. The 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 experimental materials used by the author, we found (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Reference of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Reference of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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

Wen, Yabin; Amos, Ruth I. J.; Talebi, Mohammad; Szucs, Roman; Dolan, John W.; Pohl, Christopher A.; Haddad, Paul R. published their research in Analytical Chemistry (Washington, DC, United States) on August 7 ,2018. The article was titled 《Retention Index Prediction Using Quantitative Structure-Retention Relationships for Improving Structure Identification in Nontargeted Metabolomics》.Recommanded Product: 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The article contains the following contents:

Structure identification in nontargeted metabolomics based on liquid-chromatog. coupled to mass spectrometry (LC-MS) remains a significant challenge. Quant. structure-retention relation (QSRR) modeling is a technique capable of accelerating the structure identification of metabolites by predicting their retention, allowing false positives to be eliminated during the interpretation of metabolomics data. 191 Compounds were grouped according to mol. weight and a QSRR study was carried out on the 34 resulting groups to eliminate false positives. Partial least squares (PLS) regression combined with a Genetic algorithm (GA) was applied to construct the linear QSRR models based on a variety of VolSurf+ mol. descriptors. A novel dual-filtering approach, which combines Tanimoto similarity (TS) searching as the primary filter and retention index (RI) similarity clustering as the secondary filter, was used to select compounds in training sets to derive the QSRR models yielding R2 of 0.8512 and an average root mean square error in prediction (RMSEP) of 8.45%. With a retention index filter expressed as ±2 standard deviations (SD) of the error, representative compounds were predicted with >91% accuracy, and for 53% of the groups (18/34), at least one false pos. compound could be eliminated. The proposed strategy can thus narrow down the number of false positives to be assessed in nontargeted metabolomics. In the experiment, the researchers used many compounds, for example, 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 54329-54-3Recommanded Product: 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid)

2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 54329-54-3) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: 2-Methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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

In 2007,Journal of Liquid Chromatography & Related Technologies included an article by Jiang, C.; Armstrong, D. W.; Lantz, A. W.; Peter, A.; Toth, G.. Formula: C10H11NO3. The article was titled 《Enantiomeric separation of synthetic amino acids using capillary zone electrophoresis》. The information in the text is summarized as follows:

Three chiral selectors, sulfated α-cyclodextrin (SAC), sulfated β-cyclodextrin (SBC), and carboxymethyl β-cyclodextrin (CMBC) were examined as run buffer additives for the separation of sixteen racemic synthetic amino acids and three prepared mixtures of chiral synthetic amino acids, using capillary zone electrophoresis. Seventeen of the nineteen synthetic amino acids were enantiomerically separated and fourteen of them were optimized to baseline using one or more chiral running buffer additives. SAC, with eleven baseline and three partial separations, and SBC, with ten baseline and four partial separations, are more broadly useful than CMBC. Increasing the chiral selector concentration improved the enantioresoln., but also produced longer analyses times. Addition of organic modifier (ethanol) increased migration times and decreased enantiomeric resolution Increasing the pH of the run buffer decreased analyses time as well as resolution Decreasing the applied voltage generally improved resolution After reading the article, we found that the author used (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Formula: C10H11NO3)

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Formula: C10H11NO3 It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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

The author of 《LC enantiomeric separation of unusual amino acids using cyclodextrin-based stationary phases》 were Remsburg, Jeffrey W.; Armstrong, Daniel W.; Peter, Antal; Toth, Geza. And the article was published in Journal of Liquid Chromatography & Related Technologies in 2008. Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The author mentioned the following in the article:

The use of cyclodextrin based stationary phases was studied for the enantiomeric separation of 20 unusual amino acids. Mobile phase, pH effects, and flow rate were optimized for each separation Separations were limited to aqueous mobile phases. Nineteen of the amino acids were separated, with seven having a resolution ≥1.5. The highest selectivities came from the alpha, acetylated beta, and 2,6-dinitrophenyl-4-trifluoromethylphenyl derivitized beta-cyclodextrin stationary phases. Amino acids containing a 1,2,3,4 tetrahydroisoquinoline carboxylic acid structure showed great compatibility with the acetylated beta-cyclodextrin. Tyrosine analogs, due to lack of retention, were not well suited to the cyclodextrin stationary phases. In addition to this study using (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, there are many other studies that have used (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) was used in this study.

(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

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