Category: tetrahydroisoquinoline

Cu^II/TEMPO-Catalyzed Enantioselective C(sp³)-H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation was written by Gao, Pei-Sen;Weng, Xin-Jun;Wang, Zhen-Hua;Zheng, Chao;Sun, Bing;Chen, Zhi-Hao;You, Shu-Li;Mei, Tian-Sheng. And the article was included in Angewandte Chemie, International Edition in 2020.Application of 207451-81-8 This article mentions the following:

A novel strategy for asym. Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochem., affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Application of 207451-81-8).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. There has been increasing research interest and speculation since 1968 in the potential formation of tetrahydroisoquinoline (TIQ) alkaloids in mammalian cells via such interactions, and in the role such TIQs may have in alcohol dependence. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.Application of 207451-81-8

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

Comparative molecular field analysis (CoMFA) models of phenylethanolamine N-methyltransferase (PNMT) and the α₂-adrenoceptor: the development of new, highly selective inhibitors of PNMT was written by Grunewald, Gary L.;Caldwell, Timothy M.;Dahanukar, Vilas H.;Jalluri, Ravi K.;Criscione, Kevin R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1999.Application of 207451-81-8 This article mentions the following:

As a guide to the development of new and more selective inhibitors of phenylethanolamine N-methyltransferase (PNMT) vs. the α₂-adrenoceptor, we have performed a comparative mol. field anal. (CoMFA) on a series of 80 benzylamine analogs. Using the models obtained, we have proposed a series of 3-trifluoromethyl-1,2,3,4-tetrahydroisoquinolines and predicted the activity of other analogs. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Application of 207451-81-8).

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. 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 207451-81-8

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

LC enantiomeric separation of unusual amino acids using cyclodextrin-based stationary phases was written by Remsburg, Jeffrey W.;Armstrong, Daniel W.;Peter, Antal;Toth, Geza. And the article was included in Journal of Liquid Chromatography & Related Technologies in 2008.Application of 151004-92-1 This article mentions the following:

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 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. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.Application of 151004-92-1

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

A novel synthesis of isoquinolone derivatives was written by Xie, Yu;Hu, Jingang;Hong, Xiaowei;Wei, Ya;Jia, Jie. And the article was included in Youji Huaxue in 2010.Electric Literature of C10H13N This article mentions the following:

Tetrahydroisoquinoline derivatives [i.e., δ-lactams] were designed and the synthesis of the target compounds was achieved by a nucleophilic substitution, cyclization reaction using Et chloroformate and benzeneethanamine derivatives as starting materials. The above-mentioned isoquinolinone derivatives are precursors for 1,2,3,4-tetrahydroisoquinoline derivatives (no data). The key step in this sequence, a cyclization reaction, was accomplished by using polyphosphoric acid (PPA) as a catalyst conveniently and effectively under solvent-free reaction conditions. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Electric Literature of C10H13N).

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. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. 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.Electric Literature of C10H13N

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.Application In Synthesis of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

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. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Application In Synthesis of 7-Methyl-1,2,3,4-tetrahydroisoquinoline).

7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.Application In Synthesis of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

Discovery of BI-2545: A Novel Autotaxin Inhibitor That Significantly Reduces LPA Levels in Vivo was written by Kuttruff, Christian A.;Ferrara, Marco;Bretschneider, Tom;Hoerer, Stefan;Handschuh, Sandra;Nosse, Bernd;Romig, Helmut;Nicklin, Paul;Roth, Gerald J.. And the article was included in ACS Medicinal Chemistry Letters in 2017.Formula: C9H10Cl3N This article mentions the following:

In an effort to find new therapeutic interventions addressing the unmet medical need of patients with idiopathic pulmonary fibrosis, we initiated a program to identify new autotaxin (ATX) inhibitors. Starting from a recently published compound (PF-8380), we identified several highly potent ATX inhibitors with improved pharmacokinetic and safety profiles. Further optimization efforts resulted in the identification of a single-digit nanomolar lead compound (BI-2545) that shows substantial lowering of LPA in vivo and is therefore considered a valuable tool for further studies. In the experiment, the researchers used many compounds, for example, 5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 73075-47-5Formula: C9H10Cl3N).

5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 73075-47-5) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is present in a number of drugs, such as tubocurarine, one of the quaternary ammonium muscle relaxants. 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.Formula: C9H10Cl3N

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

Direct chiral separation of unnatural amino acids by high-performance liquid chromatography on a ristocetin A-bonded stationary phase was written by Torok, Gabriella;Peter, Antal;Armstrong, Daniel W.;Tourwe, Drik;Toth, Geza;Sapi, Janos. And the article was included in Chirality in 2001.Application of 151004-92-1 This article mentions the following:

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. 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. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. 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

A biocatalytic redox cascade approach for one-pot deracemization of carboxyl-substituted tetrahydroisoquinolines by stereoinversion was written by Ju, Shuyun;Qian, Mingxin;Li, Jing;Xu, Gang;Yang, Lirong;Wu, Jianping. And the article was included in Green Chemistry in 2019.Category: tetrahydroisoquinoline This article mentions the following:

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids are important chiral building blocks in the pharmaceutical and fine chem. industries. However, the existing chemo-enzymic deracemization method employing D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) suffers from the requirement for a large excess of a nonselective chem. reducing agent. To explore an alternative method, we envisaged a concurrent biocatalytic oxidation and reduction cascade in one pot. Herein, we report a novel biocatalytic route for the asym. reduction of 3,4-dihydroisoquinoline-1-carboxylic acids employing Δ¹-piperidine-2-carboxylate/Δ¹-pyrrolidine-2-carboxylate reductase from Pseudomonas putida KT2440 (PpDpkA) as a biocatalyst, yielding the corresponding (S)-1-carboxyl-substituted tetrahydroisoquinolines with high conversions and enantiomeric excess (>99% ee). By combining FsDAAO and PpDpkA in one pot, a fully biocatalytic method was demonstrated for the deracemization of a range of racemic 1-carboxyl substituted tetrahydroisoquinolines to produce the corresponding (S)-enantiomers with >99% conversions and >99% ee. Furthermore, preparative-scale biotransformation of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid gave the (S)-enantiomer with 89% isolated yield and >99% ee. Taken together, we provide an enantioselective biocatalytic redox cascade method for the one-pot synthesis of enantiopure 1,2,3,4-tetrahydroisoquinoline carboxylic acids. In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Category: tetrahydroisoquinoline).

(S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.Category: tetrahydroisoquinoline

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

Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines was written by Bondinell, William E.;Chapin, Frederic W.;Girard, Gerald R.;Kaiser, Carl;Krog, Arnold J.;Pavloff, Alex M.;Schwartz, Mark S.;Silvestri, Joanne S.;Vaidya, Praful D.. And the article was included in Journal of Medicinal Chemistry in 1980.Application In Synthesis of 5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:

Of 13 compounds I (n = 1-4) 12 were prepared from the corresponding isoquinolines either by catalytic hydrogenation of the HCl or by reduction of the free base with excess B₂H₆. I were evaluated in vitro and in vivo for their ability to inhibit phenylethanolamine N-methyltransferase [9037-68-7] which catalyzes the terminal step in the biosynthesis of epinephrine [51-43-4]. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline-HCl (II) [57987-77-6] was the most effective. II was more potent than either 7- or 8-monosubstituted derivatives Structure-activity relations are discussed. In the experiment, the researchers used many compounds, for example, 5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 73075-47-5Application In Synthesis of 5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride).

5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 73075-47-5) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is present in a number of drugs, such as tubocurarine, one of the quaternary ammonium muscle relaxants. 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.Application In Synthesis of 5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride

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

Oxidation-Induced β-Selective C-H Bond Functionalization: Thiolation and Selenation of N-Heterocycles was written by Wang, Huamin;Li, Yongli;Lu, Qingquan;Yu, Mingming;Bai, Xudong;Wang, Shengchun;Cong, Hengjiang;Zhang, Heng;Lei, Aiwen. And the article was included in ACS Catalysis in 2019.Related Products of 207451-81-8 This article mentions the following:

Site-selective intermol. C-H bond functionalization is of central importance to synthetic chem. In particular, direct β-functionalization of N-heterocycles still remains a great challenge. Herein, we develop a strategy for oxidation-induced thiolation and selenation at the β-position of piperidine derivatives and 1,2,3,4-tetrahydroisoquinoline via C-H bond functionalization. Various 4-sulfenylisoquinolines, 3-sulfenylpyridines, and 4-selenylisoquinolines can be obtained by using O₂ as the only oxidant. Notably, neither a directing group nor a metal catalyst is necessary in this transformation. The preliminary mechanistic studies revealed that the oxidation and rearrangement pathway were key steps in this transformation, which provides a meaningful strategy for controlling site selectivity in the β-functionalization of N-heterocycles. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Related Products of 207451-81-8).

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. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. The dopamine-derived tetrahydroisoquinolines (TIQ) synthesized endogeneously from aldehydes and catecholamines have shown to modulate neurotransmission, central metabolism and motor activity.Related Products of 207451-81-8

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