Tag: 100-200

Imidodisulfamides. 2. Substituted 1,2,3,4-tetrahydroisoquinolinylsulfonic imides as antagonists of slow-reacting substance of anaphylaxis was written by Ali, Fadia El-Fehail;Gleason, John G.;Hill, David T.;Krell, Robert D.;Kruse, Carolyn H.;Lavanchy, Patricia G.;Volpe, Beth W.. And the article was included in Journal of Medicinal Chemistry in 1982.HPLC of Formula: 82771-59-3 The following contents are mentioned in the article:

Substituted 1,2,3,4-tetrahydroisoquinolinylsulfonic imides, e.g., I (R = H, 5-, 6-, 7-, 8-Cl, 7-MeO, 6,7,8-Cl₃) and 1,5-bis(arylcycloalkyl)imidodisulfamides, e.g. II, were prepared by condensation of the corresponding amine with ClSO₂NHSO₂Cl. In order to determine the influence of structural modifications of the imidodisulfamides on their ability to selectively antagonize SRS-A activity, a few conformationally constrained structures were examined Among these derivatives having a conformationally restricted alkylene side chain, substituted 1,2,3,4-tetrahydroisoquinolinylsulfonic imides produced optimum SRS-A antagonist activity and selectivity. These compounds were tested for antagonism of partially purified SRS-A induced contractions of isolated guinea pig ileum. In this series of tetrahydroisoquinolines, the effect of aromatic ring substitution, as well as substitution and variation of the size of the heterocyclic ring on SRS-A antagonist activity and selectivity, was studied. This study involved multiple reactions and reactants, such as 1-(1,2,3,4-Tetrahydroisoquinolin-7-yl)ethanone (cas: 82771-59-3HPLC of Formula: 82771-59-3).

1-(1,2,3,4-Tetrahydroisoquinolin-7-yl)ethanone (cas: 82771-59-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. 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.HPLC of Formula: 82771-59-3

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

Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase was written by Grunewald, Gary L.;Seim, Mitchell R.;Bhat, Seema R.;Wilson, Marc E.;Criscione, Kevin R.. And the article was included in Bioorganic & Medicinal Chemistry in 2008.Reference of 82771-59-3 The following contents are mentioned in the article:

A series of substituted 4,5,6,7-tetrahydrothieno[3,2-c]pyridines (THTPs) was synthesized and evaluated for their human phenylethanolamine N-methyltransferase (hPNMT) inhibitory potency and affinity for the α₂-adrenoceptor. The THTP nucleus was suggested as an isosteric replacement for the 1,2,3,4-tetrahydroisoquinoline (THIQ) ring system on the basis that 3-thienylmethylamine was more potent as an inhibitor of hPNMT and more selective toward the α₂-adrenoceptor than benzylamine. Although the isosterism was confirmed, with similar influence of functional groups and chirality in both systems on hPNMT inhibitory potency and selectivity, the THTP compounds proved, in general, to be less potent as inhibitors of hPNMT than their THIQ counterparts, with the drop in potency being primarily attributed to the electronic properties of the thiophene ring. A hypothesis for the reduced hPNMT inhibitory potency of these compounds has been formed on the basis of mol. modeling and docking studies using the x-ray crystal structures of hPNMT cocrystd. with THIQ-type inhibitors and S-adenosyl-L-homocysteine as a template. This study involved multiple reactions and reactants, such as 1-(1,2,3,4-Tetrahydroisoquinolin-7-yl)ethanone (cas: 82771-59-3Reference of 82771-59-3).

1-(1,2,3,4-Tetrahydroisoquinolin-7-yl)ethanone (cas: 82771-59-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. 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.Reference of 82771-59-3

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

Synthesis, Biochemical Evaluation, and Classical and Three-Dimensional Quantitative Structure-Activity Relationship Studies of 7-Substituted-1,2,3,4-tetrahydroisoquinolines and Their Relative Affinities toward Phenylethanolamine N-Methyltransferase and the α₂-Adrenoceptor was written by Grunewald, Gary L.;Dahanukar, Vilas H.;Jalluri, Ravi K.;Criscione, Kevin R.. And the article was included in Journal of Medicinal Chemistry in 1999.HPLC of Formula: 82771-59-3 The following contents are mentioned in the article:

7-Substituted-1,2,3,4-tetrahydroisoquinolines (7-substituted-THIQs) are potent inhibitors of phenylethanolamine N-methyltransferase (PNMT, EC 2.1.1.28), the enzyme involved in the biosynthesis of epinephrine. Unfortunately, most of these compounds also exhibit strong affinity for the α₂-adrenoceptor. To design a selective (PNMT vs α₂-adrenoceptor affinity) inhibitor of PNMT, the steric and electrostatic factors responsible for PNMT inhibitory activity and α₂-adrenoceptor affinity were investigated by evaluating a number of 7-substituted-THIQs. A classical quant. structure-activity relationship (QSAR) study resulted in a three-parameter equation for PNMT (PNMT pK_i = 0.599π – 0.0725MR + 1.55σ_m + 5.80; n = 27, r = 0.885, s = 0.573) and a three-parameter equation for the α₂-adrenoceptor (α₂ pK_i = 0.599π – 0.0542MR – 0.951σ_m + 6.45; n = 27, r = 0.917, s = 0.397). These equations indicated that steric effects and lipophilicity play a similar role at either active site but that electronic effects play opposite roles at either active site. Two binding orientations for the THIQs were postulated such that lipophilic and hydrophilic 7-substituents would not occupy the same region of space at either binding site. Using these two binding orientations, based on the lipophilicity of the 7-substituent, comparative mol. field anal. (CoMFA) models were developed that showed that the steric and electrostatic interactions at both sites were similar to those previously elaborated in the QSAR analyses. Both the QSAR and the CoMFA analyses showed that the steric interactions are similar at the PNMT active site and at the α₂-adrenoceptor and that the electrostatic interactions were different at the two sites. This difference in electrostatic interactions might be responsible for the selectivity of THIQs bearing a nonlipophilic electron-withdrawing group at the 7-position. These QSAR and CoMFA results will be useful in the design of potent and selective (PNMT vs α₂-adrenoceptor affinity) inhibitors of PNMT. This study involved multiple reactions and reactants, such as 1-(1,2,3,4-Tetrahydroisoquinolin-7-yl)ethanone (cas: 82771-59-3HPLC of Formula: 82771-59-3).

1-(1,2,3,4-Tetrahydroisoquinolin-7-yl)ethanone (cas: 82771-59-3) 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.HPLC of Formula: 82771-59-3

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

Donella-Deana, Arianna; Ruzza, Paolo; Cesaro, Luca; Brunati, Anna Maria; Calderan, Andrea; Borin, Gianfranco; Pinna, Lorenzo A. published an article in FEBS Letters. The title of the article was 《Specific monitoring of Syk protein kinase activity by peptide substrates including constrained analogs of tyrosine》.Quality Control of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid The author mentioned the following in the article:

The ability of Syk protein tyrosine kinase (PTK) to phosphorylate peptides where tyrosine is replaced by conformationally constrained analogs has been exploited to develop highly selective substrates suitable for the specific monitoring of Syk activity. In particular we have synthesized a peptidomimetic, RRRAAEDDE(L-Htc)EEV (syktide), with the 3(S)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxyl acid residue (L-Htc) substituted for tyrosine. Although syktide is phosphorylated by Syk with remarkable efficiency (Kcat = 73 min-1, Km = 11 μM), it is not affected to any appreciable extent by a variety of PTKs tested thus far. These properties make syktide the first choice as substrate for the specific monitoring of Syk. 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: 152286-30-1Quality Control 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.Quality Control 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

Computed Properties of C10H11NO3On November 30, 2001 ,《Direct chiral separation of unnatural amino acids by high-performance liquid chromatography on a ristocetin A-bonded stationary phase》 appeared in Chirality. The author of the article were Torok, Gabriella; Peter, Antal; Armstrong, Daniel W.; Tourwe, Drik; Toth, Geza; Sapi, Janos. The article conveys some information:

Direct HPLC chiral separation of numerous underivatized unnatural amino acids on a ristocetin A-bonded chiral stationary phase used in the reversed-phase and in the polar organic chromatog. modes is reported. The effects of different parameters such as mobile phase composition, temperature, and the structure of the analytes on the selectivity in both chromatog. modes are discussed. By variation of the parameters, the separation of the stereoisomers was optimized and, as a result, baseline resolution was achieved in most cases. The experimental process involved the reaction of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Computed Properties 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.Computed Properties 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

Peter, A.; Torok, G.; Toth, G.; Van den Nest, W.; Laus, G.; Tourwe, D.; Armstrong, D. W. published an article in Chromatographia. The title of the article was 《Enantiomeric separation of unusual secondary aromatic amino acids》.Category: tetrahydroisoquinoline The author mentioned the following in the article:

High-performance liquid chromatog. and gas chromatog. methods were developed for the separation of unusual secondary aromatic amino acids. Amino acids containing 1,2,3,4-tetrahydroisoquinoline, 1,2,3,4-tetrahydronorharmane-1-carboxylic acid and 1,2,3,4-tetrahydro-3-carboxy-2-carboline moieties were synthesized in racemic or chiral forms. The high-performance liquid chromatog. was carried out either on a teicoplanin-containing chiral stationary phase or on an achiral C18 column. In the latter case the diastereomers of the amino acids formed by precolumn derivatization with the chiral reagents 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate or 1-fluoro-2,4-dinitropheny1-5-L-alanine amide were separated The gas chromatog. analyses were based on separation on a Chirasil-L-Val column. 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: 152286-30-1Category: tetrahydroisoquinoline) 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.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

Recommanded Product: 152286-30-1On March 18, 2008, Liu, Cong; Thomas, James B.; Brieaddy, Larry; Berrang, Bertold; Carroll, F. Ivy published an article in Synthesis. The article was 《An improved synthesis of (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid》. The article mentions the following:

An improved synthesis of (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is described wherein a modified Pictet-Spengler reaction was employed to provide 95% yield of the product with 7% racemization or less. The enantiomeric excess of the final product was improved to 99.4% via recrystallization The overall yield of this four-step synthesis provides the title compound in 43% starting from D-tyrosine.(R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Recommanded Product: 152286-30-1) 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: 152286-30-1 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 2015,PLoS One included an article by Sarkar, Sourav; Pires, Marcos M.. Application In Synthesis of (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. The article was titled 《D-Amino acids do not inhibit biofilm formation in Staphylococcus aureus》. The information in the text is summarized as follows:

Bacteria can either exist in the planktonic (free floating) state or in the biofilm (encased within an organic framework) state. Bacteria biofilms cause industrial concerns and medical complications and there has been a great deal of interest in the discovery of small mol. agents that can inhibit the formation of biofilms or disperse existing structures. Herein it was shown that, contrary to previously published reports, D-amino acids do not inhibit biofilm formation of Bacillus subtilis (B. subtilis), Staphylococcus aureus (S. aureus), and Staphylococcus epidermis (S. epidermis) at millimolar concentrations The authors evaluated a diverse set of natural and unnatural D-amino acids and observed no activity from these compounds in inhibiting biofilm formation. In the experimental materials used by the author, we found (R)-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(cas: 152286-30-1Application In Synthesis 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.Application In Synthesis 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

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

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