Author: tianli

Copper-catalyzed N-arylation and aerobic oxidation: one-pot synthesis of tetrahydroisoquinolino[2,1-a]quinazolinone derivatives was written by Tian, Hua;Qiao, Hongwei;Zhu, Changjin;Fu, Hua. And the article was included in RSC Advances in 2014.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

An efficient and practical copper-catalyzed one-pot method for synthesis of tetrahydroisoquinolino[2,1-a]quinazolinone derivatives, e.g., I, has been developed, and the corresponding target products were prepared in moderate to good yields. The one-pot approach underwent sequential copper-catalyzed N-arylation, intramol. aerobic oxidative cyclization, and the newly synthesized products provided diverse structures for screening of biol. mols. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Quality Control 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. Among them, 1-substituted tetrahydroisoquinolines are privileged scaffolds in drugs and pharmaceuticals. 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.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

Synthesis of optically pure (R)- and (S)-tetrahydroisoquinoline-1- and -3-carboxylic acids was written by Kurata, Kaoruko;Inoue, Kumiko;Nishimura, Kazuhiko;Hoshiya, Naoyuki;Kawai, Nobuyuki;Uenishi, Junichi. And the article was included in Synthesis in 2015.Recommanded Product: (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid This article mentions the following:

The synthesis of (R)- and (S)-tetrahydroisoquinoline-1-carboxylic acids was achieved from N-Boc-protected (R)- and (S)-1-propenyltetrahydroisoquinoline (Boc = tert-butoxycarbonyl), resp., in a three-step sequence of ozonolysis, NaBH4 reduction, oxidation, and deprotection of the N-Boc group. Similarly, (S)-tetrahydroisoquinoline-3-carboxylic acids were obtained from N-Boc-protected (S)-3-(4-phenylbutenyl)tetrahydroisoquinolines. This synthetic route provides tetrahydroisoquinoline ring-based cyclic amino acids in enantiomerically pure form in a practical and efficient manner. In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Recommanded Product: (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid).

(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. 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.Recommanded Product: (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid

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

The influence of substitution at aromatic part of 1,2,3,4-tetrahydroisoquinoline on in vitro and in vivo 5-HT_1A/5-HT_2A receptor activities of its 1-adamantoyloaminoalkyl derivatives was written by Bojarski, Andrzej J.;Mokrosz, Maria J.;Minol, Sijka Charakchieva;Koziol, Aneta;Wesolowska, Anna;Tatarczynska, Ewa;Klodzinska, Aleksandra;Chojnacka-Wojcik, Ewa. And the article was included in Bioorganic & Medicinal Chemistry in 2001.Formula: C10H13N This article mentions the following:

Further structure-activity relation (SAR) studies with the 1,2,3,4-tetrahydroisoquinoline (THIQ) class of 5-HT_1A ligands led to the synthesis of new 1-adamantoyloaminoalkyl derivatives The impact of substituent variations in the aromatic part of THIQ moiety on 5-HT_1A and 5-HT_2A receptor affinities, as well as in vivo functional properties of the investigated compounds were discussed. It was found that those modifications reduced the binding affinity for 5-HT_1A receptors (in comparison with unsubstituted THIQ derivatives); however, the majority of new compounds still remained potent 5-HT_1A ligands (K_i=4.9-46 nM) and most of them showed features of partial agonists of postsynaptic 5-HT_1A receptors. At the same time, their 5-HT_2A receptor affinity was slightly increased (K_i=40-1475 nM), which resulted in a loss of 5-HT_2A/5-HT_1A selectivity. 5-Br,8-OCH₃ derivative, the most potent, mixed 5-HT_1A/5-HT_2A ligand-produced activation of presynaptic 5-HT_1A receptors and showed properties of a 5-HT_2A receptor antagonist. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Formula: 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. Among them, 1-substituted tetrahydroisoquinolines are privileged scaffolds in drugs and pharmaceuticals. 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: C10H13N

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

Hydroxyguanidines. New class of antihypertensive agents was written by Bailey, Denis M.;DeGrazia, C. George;Lape, Harlan E.;Frering, Richard;Fort, Dorothy;Skulan, Thomas. And the article was included in Journal of Medicinal Chemistry in 1973.HPLC of Formula: 207451-81-8 This article mentions the following:

3,4-Dihydro-1-methyl-2(1H)-isoquinolinecarboxamidoxime (I) [26193-33-9] and (1R,3S)-3,4-dihydro-1,3-dimethyl-2(1H)-isoquinolinecarboxamidoxime (II) [39219-29-9] had strong antihypertensive activity in exptl. hypertensive rats and dogs (oral ED 0.3-1.25 mg/kg/day chronically in dogs for both compounds). Cross-circulation experiments, in which the head vasculature of a dog was isolated from the systemic circulation and supplied with blood from a donor animal treated with I or II, showed that they penetrated the blood-brain barrier and produced centrally-induced systemic blood pressure decreases, owing to their reduced basicity compared to the corresponding guanidines. I was prepared by reaction of 1,2,3,4-tetrahydro-1-methylisoquinoline [4965-09-7] with cyanogen bromide [506-68-3], and reaction of the resulting nitrile with NH2OH. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8HPLC of Formula: 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. Among them, 1-substituted tetrahydroisoquinolines are privileged scaffolds in drugs and pharmaceuticals. 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.HPLC of Formula: 207451-81-8

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

Catalyst-free cyclization of anthranils and cyclic amines: one-step synthesis of rutaecarpine was written by Li, Jian;Wang, Zheng-Bing;Xu, Yue;Lu, Xue-Chen;Zhu, Shang-Rong;Liu, Li. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2019.Electric Literature of C10H13N This article mentions the following:

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between com. available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without addnl. catalysts, and offers a practical way for the preparation of rutaecarpine [I + II → III (80%)] and its derivatives with structural diversity. 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 can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Arene/Ru/TsDPEN complexes bearing a heterocyclic group catalyze the asymmetric transfer hydrogenation (ATH) of 1-aryl dihydroisoquinolines (DHIQs) to provide tetrahydroisoquinolines of high enantiomeric excess.Electric Literature of C10H13N

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

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

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

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

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