Author: tianli

Discovery of a small-molecule inhibitor and cellular probe of Keap1-Nrf2 protein-protein interaction was written by Hu, Longqin;Magesh, Sadagopan;Chen, Lin;Wang, Lili;Lewis, Timothy A.;Chen, Yu;Khodier, Carol;Inoyama, Daigo;Beamer, Lesa J.;Emge, Thomas J.;Shen, Jian;Kerrigan, John E.;Kong, Ah-Ng Tony;Dandapani, Sivaraman;Palmer, Michelle;Schreiber, Stuart L.;Munoz, Benito. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Electric Literature of C10H11NO2 This article mentions the following:

A high-throughput screen (HTS) of the MLPCN library using a homogeneous fluorescence polarization assay identified a small mol. as a first-in-class direct inhibitor of Keap1-Nrf2 protein-protein interaction. The HTS hit has three chiral centers; a combination of flash and chiral chromatog. separation demonstrated that Keap1-binding activity resides predominantly in one stereoisomer ML334 (LH601A; I), which is at least 100× more potent than the other stereoisomers. The stereochem. of the four cis isomers was assigned using x-ray crystallog. and confirmed using stereospecific synthesis. I is functionally active in both an ARE gene reporter assay and an Nrf2 nuclear translocation assay. The stereospecific nature of binding between I and Keap1 as well as the preliminary but tractable structure-activity relationships support its use as a lead for our ongoing optimization. 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. 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 C10H11NO2

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

Iron-catalyzed α-C-H functionalization of π-bonds: cross-dehydrogenative coupling and mechanistic insights was written by Wang, Yidong;Zhu, Jin;Guo, Rui;Lindberg, Haley;Wang, Yi-Ming. And the article was included in Chemical Science in 2020.Application In Synthesis of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

In this article, the use of dicarbonyl cyclopentadienyliron(II) complexes for the generation of propargylic anion equivalent toward the direct electrophilic functionalization of propargylic C-H bonds under mild, catalytic conditions were reported. This technol. was applied to the direct conversion of C-H bonds to C-C bonds for the synthesis of several functionalized scaffolds through a one-pot cross dehydrogenative coupling reaction with tetrahydroisoquinoline and related privileged heterocyclic scaffolds. A series of NMR studies and deuterium-labeling experiments indicated that the deprotonation of the propargylic C-H bond was the rate-determining step when a Cp*Fe(CO)₂-based catalyst system was employed. 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. 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.Application In Synthesis of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

Enantiomeric separation of unusual secondary aromatic amino acids was written by Peter, A.;Torok, G.;Toth, G.;Van den Nest, W.;Laus, G.;Tourwe, D.;Armstrong, D. W.. And the article was included in Chromatographia in 1998.Reference of 151004-92-1 This article mentions the following:

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 the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Reference 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. 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.Reference of 151004-92-1

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

Room temperature synthesis of isoquino[2,1-a][3,1]oxazine and isoquino[2,1-a]pyrimidine derivatives via visible light photoredox catalysis was written by Xuan, Jun;Feng, Zhu-Jia;Duan, Shu-Wen;Xiao, Wen-Jing. And the article was included in RSC Advances in 2012.HPLC of Formula: 207451-81-8 This article mentions the following:

A novel and efficient construction of isoquino[2,1-a][3,1]oxazine and isoquino[2,1-a]pyrimidine frameworks has been realized by means of visible light photocatalytic reactions using air as the oxidant at room temperature This strategy offers a direct and rapid access to two kinds of biol. important fused heterocycles in good to excellent yields. 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 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.HPLC of Formula: 207451-81-8

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

Electrosynthesis of polycyclic quinazolinones and rutaecarpine from isatoic anhydrides and cyclic amines was written by Chen, Xingyu;Zhang, Xing;Lu, Sixian;Sun, Peng. And the article was included in RSC Advances in 2020.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

A direct decarboxylative cyclization between readily available isatoic anhydrides I [R = H, 8-Me, 5,7-(Cl)₂, etc.] and cyclic amines II (R¹ = H, Me, OMe, F, NO₂; R² = H, OMe; n = 0, 1) was established to construct polycyclic fused quinazolinones III [R³ = H, 11-OMe, 9,11-(Cl)₂, etc.] employing electrochem. methods. This procedure was performed in an undivided cell without the use of a transition-metal-catalyst and external oxidant. A broad scope of polycyclic fused quinazolinones III was obtained in moderate to good yields. Addnl., rutaecarpine was also prepared through this method in one step in good yield. 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. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. 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.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

Enantiomeric separation of synthetic amino acids using capillary zone electrophoresis was written by Jiang, C.;Armstrong, D. W.;Lantz, A. W.;Peter, A.;Toth, G.. And the article was included in Journal of Liquid Chromatography & Related Technologies in 2007.Electric Literature of C10H11NO2 This article mentions the following:

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 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 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.Electric Literature of C10H11NO2

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

Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH₄)₂S₂O₈-Promoted Intramolecular Oxidative Cyclization was written by Xie, Lijuan;Lu, Cong;Jing, Dong;Ou, Xinrui;Zheng, Ke. And the article was included in European Journal of Organic Chemistry in 2019.COA of Formula: C10H13N This article mentions the following:

An efficient metal-free, (NH₄)₂S₂O₈ mediated intramol. oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle. In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8COA of Formula: 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 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.COA of Formula: C10H13N

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

Visible-light-driven electrocyclization of activated allylic amines via azomethine ylide formation was written by Yadav, Arvind K.;Yadav, Lal Dhar S.. And the article was included in Tetrahedron Letters in 2015.Synthetic Route of C10H13N This article mentions the following:

Visible-light-driven aerobic oxidative 6π-electrocylization of tetrahydroisoquinoline (THIQ) derived activated allylic amines leading to functionalized tricyclic N-heterocycles is reported. The reaction proceeds through visible light-induced formation of the iminium ion followed by azomethine ylide generation, and cyclization steps. This is the first example of visible light-initiated catalytic electrocyclization reaction at room temperature In the experiment, the researchers used many compounds, for example, 7-Methyl-1,2,3,4-tetrahydroisoquinoline (cas: 207451-81-8Synthetic Route of C10H13N).

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. 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.Synthetic Route of C10H13N

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

Metal- and Additive-Free Aerobic Dehydrogenation of N-Heterocycles and Hydrocarbons by N-Doped Carbon was written by Shang, Sensen;Li, Yingguang;Lv, Ying;Dai, Wen. And the article was included in Asian Journal of Organic Chemistry in 2022.HPLC of Formula: 207451-81-8 This article mentions the following:

N-doped hierarchical pore carbons (N-HPCs) derived from readily available biomass (flour) efficiently catalyzed aerobic dehydrogenation of N-heterocycles without any additives under mild conditions was describeed, owing to N dopant and high surface area indicated by characterization anal. A wide range of N-heteroarenes including quinolines, quinolinol, dihydroisoquinolines, isoquinolines, indoles, quinoxaline and acridine were obtained in good to excellent yields (36 examples, up to 99% yield). Mechanistic studies revealed a strikingly different non-free radical process from metal catalysts, for which an apparent activation energy of 66.4 kJ mol-1 was found. Moreover, the N-doped carbon exhibited robust stability and yielded 74.5% quinoline at the sixth reaction. This work provides a promising example for metal-free catalysis. 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. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.HPLC of Formula: 207451-81-8

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

Synthesis of tetrahydroisoquinoline and as-homotetrahydroisoquinoline bases by the glycine-aluminum chloride method. II was written by v. Braun, Julius;Wirz, Karl. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1927.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

Just as Ph(CH₂)_nN(SO₂Ph)CH₂COCl with AlCl₃ loses CO₂ and forms C₆H₄.(CH₂)_n.N(SO₂Ph).CH₂, when n = 2 or 3, so Ph(CH₂)₂NMeCH₂COCl (I) has now been found to yield N-methyltetrahydroisoquino-line (II) smoothly. The new “glycine-AlCl₃ method” of synthesizing tetrahydro- and as-homotetrahydroisoquinoline has been successfully applied to the synthesis of various derivatives of these compounds Et β-phenylethymethylglycine, Ph(CH₂)₂NMeCH₂CO₂Et, from PhCH₂CH₂NHMe in Et₂O with 0.5 mol. BrCH₂CO₂Et, b₁₂ 151 5°; methiodide, m. 160°. Frec acid, m. 163°, obtained as the HCl salt, m. 155°, by evaporating the ester with HCl; the acid with PCl₅ and cold AcCl gives the HCl salt of the chloride (I) which decomposes so rapidly in the air that it could not be accurately analyzed; this salt with AlCl₃ yields more than 40% of the HCl salt, m. 163°, of II, b. 213° (picrate, m. 146°; methiodide, m. 189°). p-MeC₆H₄CH₂CH₂OH, obtained in 80% yield from MeC₆H₄Br, Mg and ClCH₂CH₂OH, was converted through the bromide, b₁₄ 115°, and the phthalimide, MeC₆H₄CH₂CH₂N(CO)₂C₆H₄, m. 113°, into the amine, which with BrCH₂CO₂Et smoothly yielded the ester p-MeC₆H₄CH₂NHCH₂CO₂Et, b₁₂ 176-7°; this with HCl gave the free glycine-HCl, m. 216°, converted into the benzenesulfonyl derivative, MeC₆H₄CH₂CH₂N(SO₂Ph)CH₂CO₂H, which with PCl₅ and AlCl₃ yielded 65% of the benzenesulfonyl derivative, m. 154°, of 7-methyltetrahydroisoquinoline, b₁₈ 125°, d₄²⁴ 1.0176 (HCl salt, m. 216°; picrate, m. 202°; methiodide, m. 133°; NO derivative, m. 87°). β-p-Tolylethyl cyanide, from the bromide and KCN (yield, more than 90%), b₁₅ 137°, is reduced by the Ladenburg method to the propylamine, b₂₃ 126°, quickly absorbs CO₂ from the air (HCl salt, m. 225°; picrate, yellow, m. 154°; Bz derivative, m. 85°; phenylthiourea, m. 82°), gives with BrCH₂CO₂Et the ester MeC₆H₄(CH₂)₃NHCH₂CO₂Et, b₂₂ 191°. Free glycine-HCl, m. 211°; benzenesulfonyl derivative, m. 116°, yields almost 70% of the benzenesulfonyl derivative, m. 126°, of 8-methyl-as-homotetrahydroisoquinoline, b₁₉ 137-9° m. 27°, d₄²³ 1.0048 (HCl salt, m. 223°; Bz derivative, m. 101°; NO derivative, m. 91°). β-p-Isopropylphenylethyl alc. (60% from p-Me₂CHC₆H₄Br, Mg and ClCH₂CH₂OH), b₂₀ 147°; bromide, b₂₀ 134-6°; cyanide, b₁₇ 150°; propylamine. b₂₀ 143° (HCl salt, m. 196°; picrate, m. 122°; Bz derivative, m. 71°). The ester Me₂CHC₆H₄(CH₂)₃NHCH₂CO₂Et, b₂₀ 205-10°. Free acid-HCl, m. 210°; benzenesulfonyl derivative, m. 101°, yields 70% of the benzenesulfonyl derivative, m. 92°, of 8-isopropyl-as-homotetrahydroisoquinoline, m. 31° (HCl salt, m. 248°; picrate, m. 236° ; methiodide, m. 214°; Bz derivative, m. 83°; NO derivative, m. 70°). Piperonal (300 g.) can be quant. reduced in less than 1 hr. with H and Ni in decalin at 120-30° to the alc., m. 54°, b₁₈ 157°, whose chloride with KCN in aqueous Me₂CO at 100° yields with extraordinary smoothness the cyanide, m. 42°, b₃₀ 180°, and this with Na and alc. gives 60% of homopiperonylamine; the ester formed from this with BrCH₂CO₂Et is hydrolyzed with such ease that the product of the reaction is almost exclusively the free glycine-HCl, m. 241°; the benzenesulfonyl derivative, CH₂O₂C₆H₃CH₂CH₂N(SO₂Ph)CH₂CO₂H, m. 131°, yields with PCl₅ and AlCl₃ only a black semi-solid mass from which no homogeneous product could be isolated. 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. 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. 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.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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