Tag: 100-200

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

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

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

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

TBHP-Mediated Oxidative Decarboxylative Cyclization in Water: Direct and Sustainable Access to Anti-malarial Polycyclic Fused Quinazolinones and Rutaecarpine was written by Chen, Xingyu;Xia, Fei;Zhao, Yifan;Ma, Ji;Ma, Yue;Zhang, Dong;Yang, Lan;Sun, Peng. And the article was included in Chinese Journal of Chemistry in 2020.Safety of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

Polycyclic fused quinazolinones I [R = H, Cl, Br, F, Cl; R¹ = H, Me, Cl, etc.; R² = H, MeO, F, Br, Cl; R³ = H, Me; R⁴ = H, F; R⁵ = H, MeO; R⁶ = H, Me, F, Br, MeO] with anti-malarial activity were synthesized through tert-Bu hydroperoxide (TBHP)-mediated oxidative decarboxylative cyclization between com. available isatins and cyclic amines in one step. The reaction proceeded smoothly in water without addnl. transition-metal catalyst, acid and base. The newly synthesized products were evaluated to exhibit moderate to good anti-malarial activity against chloroquine drug-sensitive Plasmodium falciparum 3D7 strain. Addnl., this method also provided direct approach to rutaecarpine in good yield. 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. 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.Safety of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

NHC-catalyzed Redox-Neutral Aza-Benzoin Reaction of Aldehydes with Tetrahydroisoquinolines was written by Jiang, Di;Wu, Zijun;Wang, Jian. And the article was included in Chinese Journal of Chemistry in 2020.Related Products of 207451-81-8 This article mentions the following:

An unprecedented redox-neutral aza-benzoin protocol was reported for preparation of tetrahydroisoquinoline derivatives Upon exposure of tetrahydroisoquinolines to aromatic aldehydes in the presence of an NHC catalyst, the C-1 acylated tetrahydroisoquinolines were obtained in moderate to good yields. 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. 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.Related Products of 207451-81-8

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

Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase was written by Grunewald, Gary L.;Seim, Mitchell R.;Bhat, Seema R.;Wilson, Marc E.;Criscione, Kevin R.. And the article was included in Bioorganic & Medicinal Chemistry in 2008.Electric Literature of C10H13N This article mentions the following:

A series of substituted 4,5,6,7-tetrahydrothieno[3,2-c]pyridines (THTPs) was synthesized and evaluated for their human phenylethanolamine N-methyltransferase (hPNMT) inhibitory potency and affinity for the α₂-adrenoceptor. The THTP nucleus was suggested as an isosteric replacement for the 1,2,3,4-tetrahydroisoquinoline (THIQ) ring system on the basis that 3-thienylmethylamine was more potent as an inhibitor of hPNMT and more selective toward the α₂-adrenoceptor than benzylamine. Although the isosterism was confirmed, with similar influence of functional groups and chirality in both systems on hPNMT inhibitory potency and selectivity, the THTP compounds proved, in general, to be less potent as inhibitors of hPNMT than their THIQ counterparts, with the drop in potency being primarily attributed to the electronic properties of the thiophene ring. A hypothesis for the reduced hPNMT inhibitory potency of these compounds has been formed on the basis of mol. modeling and docking studies using the x-ray crystal structures of hPNMT cocrystd. with THIQ-type inhibitors and S-adenosyl-L-homocysteine as a template. 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, as a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids. 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 C10H13N

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

Novel pyrimidines as acid pump antagonists (APAs) was written by Yoon, Young Ae;Park, Chan Sun;Cha, Myung Hun;Choi, Hyunho;Sim, Jae Young;Kim, Jae Gyu. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C10H13N This article mentions the following:

A series of pyrimidine derivatives as acid pump antagonists (APAs) was synthesized and the inhibitory activities against H⁺/K⁺ ATPase isolated from hog gastric mucosa were determined After elaborating on substituents at C2 and C4 position of the pyrimidine scaffold, it was observed that I is a potent APA with H⁺/K⁺ ATPase, IC₅₀ = 52 nM. 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. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. 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.Formula: C10H13N

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

Design and synthesis of nitrogen-containing benzoheterocyclic derivatives and their antipsychotic activities was written by Peng, Shaoping;Yu, Leiping;Li, Jianqi. And the article was included in Yaoxue Xuebao in 2009.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline This article mentions the following:

A series of nitrogen-containing benzoheterocyclic derivatives were synthesized and tested for their antipsychotic activities. Their structures were confirmed by ¹H-NMR and HR-MS. Preliminary in vitro pharmacol. trials showed that most of the target compounds had high affinity with D₂ and 5-HT_2A receptors. Among the tested compounds, 20 compounds exhibited the highest affinity and D₂ partial agonist activities. In vivo studies showed that 20 compounds had potent antipsychotic activities on apomorphine mice model, which was a chance to find a better precursor of D₂ partial agonist for further optimization. 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. 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.Quality Control of 7-Methyl-1,2,3,4-tetrahydroisoquinoline

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

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