October 2022 | Page 2 of 7 | Heterocyclic Building Blocks-Tetrahydroisoquinoline

Xie, Feng’s team published research in ACS Catalysis in 2018-07-06 | 115955-90-3

ACS Catalysis published new progress about Atom economy. 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, COA of Formula: C9H12N2.

Xie, Feng; Chen, Qing-Hua; Xie, Rong; Jiang, Huan-Feng; Zhang, Min published the artcile< MOF-Derived Nanocobalt for Oxidative Functionalization of Cyclic Amines to Quinazolinones with 2-Aminoarylmethanols>, COA of Formula: C9H12N2, the main research area is MOF nanocobalt catalysis oxidative functionalization cyclic amine aminoarylmethanol; quinazolinone preparation.

By employing a MOF-templated method, we have developed a highly dispersed and ultralow loading cobalt nanocatalyst, which has been applied in the oxidative functionalization of easily available cyclic amines with 2-aminoarylmethanols to ring-fused quinazolinones, the core structures of numerous valuable products. The developed catalytic transformation proceeds with the merits of broad substrate scope, good functional group tolerance and chemoselectivity, high step- and atom-efficiency, and use of the naturally abundant Co/O2 system, which offers a practical way for the preparation of quinazolinones with structural diversity. The work presented has built an important basis for direct conversion of cyclic amine motifs into functional frameworks.

ACS Catalysis published new progress about Atom economy. 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, COA of Formula: C9H12N2.

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

Meyer, Michael E’s team published research in AAPS Journal in 2021-05-31 | 115955-90-3

AAPS Journal published new progress about Alcohols Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Name: 1,2,3,4-Tetrahydroisoquinolin-5-amine.

Meyer, Michael E.; Doshi, Arpit; Yasuda, Dennis; Zaveri, Nurulain T. published the artcile< Structure-Based SAR in the Design of Selective or Bifunctional Nociceptin (NOP) Receptor Agonists>, Name: 1,2,3,4-Tetrahydroisoquinolin-5-amine, the main research area is nociceptin receptor agonist binding interaction structural modification; active-state; homology model; nociceptin receptor; pharmacophore; selective or bifunctional nociceptin agonist; structure-based drug design.

The nociceptin opioid receptor (NOP), the fourth member of the opioid receptor family, and its endogenous peptide ligand, nociceptin or orphanin FQ (N/OFQ), play a vital role in several central nervous system pathways regulating pain, reward, feeding, anxiety, motor control and learning/memory. Both selective NOP agonists as well as bifunctional agonists at the NOP and mu opioid receptor (MOP) have potential therapeutic applications in CNS disorders related to these processes. Using Surflex-Dock protocols, we conducted a computational structure-activity study of four scaffold classes of NOP ligands with varying NOP-MOP selectivity. By docking these compounds into the orthosteric binding sites within an active-state NOP homol. model, and an active-state MOP crystal structure, the goal of this study was to use a structure-based drug design approach to modulate NOP affinity and NOP vs.MOP selectivity. We first docked four parent compounds (no side chain) to determine their binding interactions within the NOP and MOP binding pockets. Various polar sidechains were added to the heterocyclic A-pharmacophore to modulate NOP ligand affinity. The substitutions mainly contained a 1-2 carbon chain with a polar substituent such as an amine, alc., sulfamide, or guanidine. The SAR anal. is focused on the impact of structural changes in the sidechain, such as chain length, hydrogen bonding capability, and basic vs neutral functional groups on binding affinity and selectivity at both NOP and MOP receptors. This study highlights structural modifications that can be leveraged to rationally design both selective NOP and bifunctional NOP-MOP agonists with different ratios of functional efficacy.

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

Montgomery, Deanna’s team published research in ACS Chemical Neuroscience in 2019-08-21 | 893566-75-1

ACS Chemical Neuroscience published new progress about Bromination. 893566-75-1 belongs to class tetrahydroisoquinoline, and the molecular formula is C14H18BrNO2, HPLC of Formula: 893566-75-1.

Montgomery, Deanna; Anand, Jessica P.; Griggs, Nicholas W.; Fernandez, Thomas J.; Hartman, Joshua G.; Sanchez-Santiago, Ashley A.; Pogozheva, Irina D.; Traynor, John R.; Mosberg, Henry I. published the artcile< Novel dimethyltyrosine-tetrahydroisoquinoline peptidomimetics with aromatic tetrahydroisoquinoline substitutions show in vitro Kappa and Mu opioid receptor agonism>, HPLC of Formula: 893566-75-1, the main research area is dimethyltyrosine tetrahydroisoquinoline peptidomimetic synthesis opioid receptor agonist; peptidomimetic opioid structure activity mol docking cocain addiction; bromination quinoline substitution protection Suzuki coupling; cocaine addiction; dimethyltyrosine−tetrahydroisoquinoline; multifunctional ligands; opioids; peptidomimetics; synthesis.

The dimethyltyrosine-tetrahydroisoquinoline (Dmt-Tiq) scaffold was originally developed in the production of selective delta opioid receptor (DOR) antagonists. Installation of a 7-benzyl pendant on the tetrahydroisoquinoline core of this classic opioid scaffold introduced kappa opioid receptor (KOR) agonism. Further modification of this pendant resulted in retention of KOR agonism and the addition of mu opioid receptor (MOR) partial agonism, a bifunctional profile with potential to be used in the treatment of cocaine addiction.

ACS Chemical Neuroscience published new progress about Bromination. 893566-75-1 belongs to class tetrahydroisoquinoline, and the molecular formula is C14H18BrNO2, HPLC of Formula: 893566-75-1.

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

Mach, Ulrich R’s team published research in ChemBioChem in 2004-04-02 | 115955-90-3

ChemBioChem published new progress about Dopamine D3 receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 115955-90-3 belongs to class tetrahydroisoquinoline, and the molecular formula is C9H12N2, Product Details of C9H12N2.

Mach, Ulrich R.; Hackling, Anneke E.; Perachon, Sylvie; Ferry, Sandrine; Wermuth, Camille G.; Schwartz, Jean-Charles; Sokoloff, Pierre; Stark, Holger published the artcile< Development of novel 1,2,3,4-tetrahydroisoquinoline derivatives and closely related compounds as potent and selective dopamine D3 receptor ligands>, Product Details of C9H12N2, the main research area is tetrahydroisoquinoline derivative dopamine D3 receptor ligand.

Based on N-alkylated 1,2,3,4-tetrahydroisoquinoline derivatives which are structurally related to the partial agonist BP 897, a series of novel, selective dopamine D3 receptor antagonists has been synthesized. Derivatization included changes in the arylamide moiety and the tetrahydroisoquinoline substructure leading to compounds with markedly improved selectivities and affinities in the low nanomolar concentration range. From the 55 structures presented here, (E)-3-(4-iodophenyl)-N-(4-(1,2,3,4-tetrahydroisoquinolin-2-yl)butyl)acrylamide (51) has high affinity (Ki(hD3) = 12 nM) and a 123-fold preference for the D3 receptor relative to the D2 receptor subtype. Its pharmacol. profile offers the prospect of a novel radioligand as a tool for various dopamine D3-receptor-related in vitro and in vivo investigations.

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

Liu, Cong’s team published research in Synthesis in 2008 | CAS: 152286-30-1

(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.

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.

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

Sarkar, Sourav’s team published research in PLoS One in 2015 | CAS: 152286-30-1

(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.

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

Peter, A.’s team published research in Chromatographia in 1998 | CAS: 152286-30-1

(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.

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

Torok, Gabriella’s team published research in Chirality in 2001 | CAS: 152286-30-1

(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.

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

Donella-Deana, Arianna’s team published research in FEBS Letters in 2002 | CAS: 152286-30-1

(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.

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

Ansari, Monish Arbaz’s team published research in Organic Letters in 2022 | CAS: 799274-06-9

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.Application In Synthesis of 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.

《[2+3] Annulative Coupling of Tetrahydroisoquinolines with Aryliodonio diazo compounds To Access 1,2,4-Triazolo[3,4-a]isoquinolines》 was written by Ansari, Monish Arbaz; Khan, Shahnawaz; Ray, Subhasish; Shukla, Gaurav; Singh, Maya Shankar. Application In Synthesis of 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride And the article was included in Organic Letters on August 19 ,2022. The article conveys some information:

Base promoted one-pot annulative coupling of 1,2,3,4-tetrahydroisoquinolines (THIQs) with hypervalent iodine(III) species aryliodonio diazo compounds I (R = COOEt, COOtBu, COOBn, menthyl) has been devised for the direct construction of 1,2,4-triazolo[3,4-a]isoquinoline derivatives II (R = COOEt, COOtBu, COOBn, menthyl; R1 = H, 7-Me, 9-F, etc.) at room temperature in open air for the first time. This approach involves [2+3] cascade annulation of nucleophilic THIQ with an electrophilic aryliodonio diazo compound via N-H and α-C1(sp3)-H difunctionalization of THIQ. In the experiment, the researchers used many compounds, for example, 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9Application In Synthesis of 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride)

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