Category: tetrahydroisoquinoline

Application of a new chiral derivatizing agent to the enantioseparation of secondary amino acids was written by Peter, Antal;Vekes, Erika;Toth, Geza;Tourwe, Dirk;Borremans, Frans. And the article was included in Journal of Chromatography A in 2002.Electric Literature of C10H11NO2 This article mentions the following:

A new chiral derivatizing agent, (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester, (S)-NIFE, was applied for the HPLC separation of enantiomers of 19 unnatural secondary amino acids: proline, pipecolic acid analogs, piperazine-2-carboxylic acid, morpholine-3-carboxylic acid, thiomorpholine-3-carboxylic acid and analogs containing the 1,2,3,4-tetrahydroisoquinoline, 1,2,3,4-tetrahydronorharmane, 1,2,3,4-tetrahydro-2-carboline and 2-benzazepine skeletons. Excellent resolutions were achieved for most of the studied compounds by using a reversed-phase mobile phase system. The conditions of separation were optimized by variation of the mobile phase composition In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Electric Literature 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. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. 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.Electric Literature 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;Laus, Georges;Tourwe, Dirk. And the article was included in Journal of Chromatography A in 1998.COA of Formula: C10H11NO2 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: 151004-92-1COA of Formula: 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. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.COA of Formula: C10H11NO2

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

Discovery of a Parenteral Small Molecule Coagulation Factor XIa Inhibitor Clinical Candidate (BMS-962212) was written by Pinto, Donald J. P.;Orwat, Michael J.;Smith, Leon M.;Quan, Mimi L.;Lam, Patrick Y. S.;Rossi, Karen A.;Apedo, Atsu;Bozarth, Jeffrey M.;Wu, Yiming;Zheng, Joanna J.;Xin, Baomin;Toussaint, Nathalie;Stetsko, Paul;Gudmundsson, Olafur;Maxwell, Brad;Crain, Earl J.;Wong, Pancras C.;Lou, Zhen;Harper, Timothy W.;Chacko, Silvi A.;Myers, Joseph E.;Sheriff, Steven;Zhang, Huiping;Hou, Xiaoping;Mathur, Arvind;Seiffert, Dietmar A.;Wexler, Ruth R.;Luettgen, Joseph M.;Ewing, William R.. And the article was included in Journal of Medicinal Chemistry in 2017.SDS of cas: 207451-81-8 This article mentions the following:

Factor XIa (FXIa) is a blood coagulation enzyme that is involved in the amplification of thrombin generation. Mounting evidence suggests that direct inhibition of FXIa can block pathol. thrombus formation while preserving normal hemostasis. Preclin. studies using a variety of approaches to reduce FXIa activity, including direct inhibitors of FXIa, have demonstrated good antithrombotic efficacy without increasing bleeding. Based on this potential, the authors targeted the efforts at identifying potent inhibitors of FXIa with a focus on discovering an acute antithrombotic agent for use in a hospital setting. Herein the authors describe the discovery of a potent FXIa clin. candidate, I (FXIa Ki = 0.7 nM), with excellent preclin. efficacy in thrombosis models and aqueous solubility suitable for i.v. administration. BMS-962212 is a reversible, direct, and highly selective small mol. inhibitor of FXIa. 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. 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.SDS of cas: 207451-81-8

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

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

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

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

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

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

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