Tag: 100-200

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

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

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

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

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

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

Shonberg, Jeremy; Draper-Joyce, Christopher; Mistry, Shailesh N.; Christopoulos, Arthur; Scammells, Peter J.; Lane, J. Robert; Capuano, Ben published an article in Journal of Medicinal Chemistry. The title of the article was 《Structure-activity study of N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652), a bitopic ligand that acts as a negative allosteric modulator of the dopamine D2 receptor》.Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride The author mentioned the following in the article:

The authors recently demonstrated that SB269652 I engages one protomer of a dopamine D2 receptor (D2R) dimer in a bitopic mode to allosterically inhibit the binding of dopamine at the other protomer. Herein, the authors investigate structural determinants for allostery, focusing on modifications to three moieties within I. The authors find that orthosteric “”head”” groups with small 7-substituents were important to maintain the limited neg. cooperativity of analogs of I, and replacement of the tetrahydroisoquinoline head group with other D2R “”privileged structures”” generated orthosteric antagonists. Addnl., replacement of the cyclohexylene linker with polymethylene chains conferred linker length dependency in allosteric pharmacol. The authors validated the importance of the indolic NH as a hydrogen bond donor moiety for maintaining allostery. Replacement of the indole ring with azaindole conferred a 30-fold increase in affinity while maintaining neg. cooperativity. Combined, these results provide novel SAR insight for bitopic ligands that act as neg. allosteric modulators of the D2R. In the experiment, the researchers used 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride)

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.Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride 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

Synthetic Route of C10H11NO3On March 13, 2017, Barnash, Kimberly D.; The, Juliana; Norris-Drouin, Jacqueline L.; Cholensky, Stephanie H.; Worley, Beau M.; Li, Fengling; Stuckey, Jacob I.; Brown, Peter J.; Vedadi, Masoud; Arrowsmith, Cheryl H.; Frye, Stephen V.; James, Lindsey I. published an article in ACS Combinatorial Science. The article was 《Discovery of Peptidomimetic Ligands of EED as Allosteric Inhibitors of PRC2》. The article mentions the following:

The function of EED within Polycomb repressive complex 2 (PRC2) is mediated by a complex network of protein-protein interactions. Allosteric activation of PRC2 by binding of methylated proteins to EED’s aromatic cage is essential for full catalytic activity, but details of this regulation are not fully understood. EED’s recognition of the product of PRC2 activity, histone H3 lysine 27 trimethylation (H3K27me3), stimulates PRC2 methyltransferase activity at adjacent nucleosomes leading to H3K27me3 propagation and, ultimately, gene repression. By coupling combinatorial chem. and structure-based design, we optimized a low affinity methylated Jarid2 peptide to a smaller, more potent peptidomimetic ligand (Kd = 1.14 ± 0.14 μM) of the aromatic cage of EED. Our strategy illustrates the effectiveness of applying combinatorial chem. to achieve both ligand potency and property optimization. Furthermore, the resulting ligands, UNC5114 and UNC5115, demonstrate that targeted disruption of EED’s reader function can lead to allosteric inhibition of PRC2 catalytic activity. In the experimental materials used by the author, we found (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Synthetic Route of 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.Synthetic Route of 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

Category: tetrahydroisoquinolineOn October 10, 2014 ,《Direct high-performance liquid chromatographic enantioseparation of secondary amino acids on Cinchona alkaloid-based chiral zwitterionic stationary phases. Unusual temperature behavior》 was published in Journal of Chromatography A. The article was written by Ilisz, Istvan; Gecse, Zsanett; Pataj, Zoltan; Fulop, Ferenc; Toth, Geza; Lindner, Wolfgang; Peter, Antal. The article contains the following contents:

Two chiral stationary phases containing a quinine- or a quinidine-based zwitterionic ion-exchanger as chiral selector were applied for the enantioseparation of 27 unusual cyclic secondary α-amino acids. The effects of the nature and concentration of the bulk solvent, the acid and base additives, the structures of the analytes and temperature on the enantioresoln. were studied. To study the effects of temperature and to obtain thermodn. parameters, experiments were carried out at constant mobile phase compositions in the temperature range -5 to 55°. The thermodn. parameters indicated that in most cases the separations were enthalpy-driven, but some entropy-driven separations were also observed The sequence of elution of the enantiomers was determined in most cases. In the experiment, the researchers used (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Category: tetrahydroisoquinoline)

(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.Category: tetrahydroisoquinoline 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

Peter, Antal; Toth, Geza; Olajos, Edit; Fueloep, Ferenc; Tourwe, Dirk published an article in Journal of Chromatography A. The title of the article was 《Monitoring of optical isomers of some conformationally constrained amino acids with tetrahydroisoquinoline or tetraline ring structures. Part II》.Formula: C10H11NO3 The author mentioned the following in the article:

Conformationally constrained amino acids were synthesized in chiral or racemic forms: D- and L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic), the erythro-D,L-4-Me analog, D- and L-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, D- and L-7-hydroxy-6,8-diiodo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, D,L-2-aminotetraline-2-carboxylic acid, D,L-6-hydroxy-2-aminotetraline-2-carboxylic acid and D,L-6-methoxy-2-aminotetraline-2-carboxylic acid. The optical isomers were characterized and identified by applying precolumn derivatization with chiral reagents (1-fluoro-2,4-dinitrophenyl-5-L-alanine amide and 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate) and enzymic digestion with L-amino acid oxidase, carboxypeptidase A and α-chymotrypsin. The HPLC conditions (pH, eluent composition and different buffers) were varied to obtain optimum separations 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: 152286-30-1Formula: 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