42923-77-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-1,2,3,4-tetrahydroisoquinoline is used as a key intermediate in the synthesis of novel spirobicyclic Artemisinin (A777500) analogues for their anti-tumor activity. These analogues have shown promising results in targeting and inhibiting the growth of cancer cells, making them valuable candidates for further research and development in oncology.

InChI:InChI=1/C10H13NO/c1-12-10-3-2-9-7-11-5-4-8(9)6-10/h2-3,6,11H,4-5,7H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 22246-12-4 6-methoxy-1,2,3,4-tetrahydro-1-oxoisoquinoline 
• 212188-99-3 6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde 
• 7647-01-0 hydrogenchloride 
• 52986-70-6 6-methoxyisoquinoline 
• 152356-73-5 (Z)-1-(3-methoxyphenyl)-2-nitroethene 
• 591-31-1 3-methoxy-benzaldehyde 
• 57854-49-6 3-(3-methoxyphenyl)propionamide 
• 33543-63-4 ethyl-N-<2-(3-methoxyphenyl)ethyl>-carbamate 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 5111-70-6 5-methoxy-1-indanone 
• 942150-85-8 bis(6-methoxy-N-1,2,3,4-tetrahydroisoquinolinyl)methane 
• 57196-62-0 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 

Downstream Products

• 152436-71-0 6-Methoxy-2-(2-nitro-benzyl)-1,2,3,4-tetrahydro-isoquinoline 
• 114688-66-3 2-(4-chloro-2-nitrobenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 59839-23-5 6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide 
• 145028-31-5 1,2,3,4-tetrahydro-6-methoxy-1-(3-methoxybenzyl)-2-pivaloylisoquinoline 
• 406234-46-6 ethyl 4-(6-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)benzoate 
• 79421-38-8 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid ethyl ester 
• 63905-73-7 6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 1064199-05-8 2-(3-methoxybenzyl)-6-sulfamoyloxy-1,2,3,4-tetrahydroisoquinoline 
• 1429253-99-5 C₂₃H₂₃N₃O₃ 

Relevant academic research and scientific papers

Inhibition of Complex I by Isoquinoline Derivatives Structurally Related to 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine (MPTP)

Mitochondrial respiratory failure secondary to complex I inhibition may contribute to the neurodegenerative process underlying nigral cell death in Parkinson's disease (PD). Isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) or 1-methyl-4-phenylpyridinium (MPP+) may be inhibitors of complex I, and have been implicated in the cause of PD as endogenous neurotoxins. To determine the potency and structural requirements of isoquinoline derivatives to inhibit mitochondrial function, we examined the effects of 22 neutral and quaternary compounds from three classes of isoquinoline derivatives (11 isoquinolines, 2 dihydroisoquinolines, and 9 1,2,3,4-tetrahydroisoquinolines) and MPP+ on the enzymes of the respiratory chain in mitochondrial fragments from rat forebrain. With the exception of norsalsolinol and N,n-propylisoquinolinium, all compounds inhibited complex I in a time-independent, but concentration-dependent manner, with IC50s ranging from 0.36-22 mM. Several isoquinoline derivatives were more potent inhibitors of complex I than 1-methyl-4-phenylpyridinium ion (MPP+) (IC50 = 4.1 mM), the most active being N-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline (IC50 = 0.36 mM) and 6-methoxy-1,2,3,4-tetrahydroisoquinoline (IC50 = 0.38 mM). 1,2,3,4-Tetrahydroisoquinoline was the least potent complex I inhibitor (IC50 ca. 22 mM). At 10 mM, only isoquinoline (23.1 percent), 6,7-dimethoxyisoquinoline (89.6 percent), and N-methylsalsolinol (34.8 percent) inhibited (P +, so respiratory inhibition may underlie their reported neurotoxicity.

Improved and practical synthesis of 6-methoxy-1,2,3,4- tetrahydroisoquinoline hydrochloride

6-Methoxy-1,2,3,4-tetrahydroisoquinoline (1) or its hydrochloride salt (4) is an expensive chemical with limited commercial availability. We report an improved and practical synthesis of 4 from inexpensive 2-(3-methoxyphenyl) ethylamine (2) using a Pictet-Spengler condensation via a novel aminal intermediate. The synthesis significantly lowers the cost and provides easy access to 6-methoxy-1,2,3,4-tetrahydroisoquinoline or its HCl salt on a large scale.

Discovery of Diaminopyrimidine Carboxamide HPK1 Inhibitors as Preclinical Immunotherapy Tool Compounds

Hematopoietic progenitor kinase 1 (HPK1), a serine/threonine kinase, is a negative immune regulator of T cell receptor (TCR) and B cell signaling that is primarily expressed in hematopoietic cells. Accordingly, it has been reported that HPK1 loss-of-function in HPK1 kinase-dead syngeneic mouse models shows enhanced T cell signaling and cytokine production as well as tumor growth inhibition in vivo, supporting its value as an immunotherapeutic target. Herein, we present the structurally enabled discovery of novel, potent, and selective diaminopyrimidine carboxamide HPK1 inhibitors. The key discovery of a carboxamide moiety was essential for enhanced enzyme inhibitory potency and kinome selectivity as well as sustained elevation of cellular IL-2 production across a titration range in human peripheral blood mononuclear cells. The elucidation of structure-activity relationships using various pendant amino ring systems allowed for the identification of several small molecule type-I inhibitors with promising in vitro profiles.

MONOCYCLIC B-LACTAM COMPOUND FOR TREATING BACTERIAL INFECTION

Disclosed are a class of new monocyclic β-lactam compounds, an isomer thereof or pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising the compounds, and the use of same in preparing drugs for treating diseases associated

INDOLINONE COMPOUNDS FOR USE AS MAP4K1 INHIBITORS

The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, ring C, X1, X2, L1, R1, R2, R3, R4, R5, R6, R7, m and n are as defined herein, which are useful as MAP4K1 inhibitors, processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by MAP4K1.

Easy Access to 2,4-Disubstituted Cyclopentenones by a Gold(III)-Catalyzed A3-Coupling/Cyclization Cascade

An efficient and convenient synthesis of 2,4-disubstituted cyclopentenones has been achieved through a Au(III)-catalyzed isomerization-A3-coupling/cyclization cascade. A possible mechanism involving an initial Au(III)-catalyzed isomerization, A3-type coupling, and cyclization via an enol intermediate is postulated.

Synthesis and evaluation of tetrahydroisoquinoline-benzimidazole hybrids as multifunctional agents for the treatment of Alzheimer's disease

A novel series of tetrahydroisoquinoline-benzimidazole hybrids have been designed and synthesized as multifunctional agents against Alzheimer's disease (AD). These compounds were evaluated for their inhibition of neuroinflammation and human β-secretase (hBACE1), and neuroprotective activity. Among them, compound BD3 possessed significant anti-neuroinflammatory activity (IC50 = 5.07 μM against nitric oxide production) through inhibiting the expression and secretion of proinflammatory cytokines in BV2 cells. Compound BD3 also exhibited moderate hBACE1 inhibitory activity (65.7% inhibition at 20 μM) and potent neuroprotective effect by increasing GSH level and reducing ROS production (91.8% cell viability at 5 μM). Parallel artificial membrane permeation assay demonstrated that BD3 could cross the blood-brain barrier (BBB). Thus, this study demonstrates that the compounds with tetrahydroisoquinoline-benzimidazole scaffold are potential anti-AD agents, and they are worth for the further development.

A multi-functional the anti-ahl tribulus sea is silent disease of the benzimidazole derivatives and its preparation method and application

The invention provides a multi-functional anti-the erzierzi sea is silent disease of benzimidazole derivative and its preparation method and application. Said styrene and imidazole derivatives having a structure of formula (I) is shown; Wherein formula (I) R in1 Is H, C1 - C5 alkyl, C1 - C5 alkoxy, halogen base, hydroxy or amino, X is C or N atom. The invention is based on the fragment assembly of the lead compound discovery method, through the tetrahydroisoquinoline and benzimidazole two fragment assembly, design is a new skeleton molecule, and synthesizing a series of benzimidazole derivatives. The present invention provides a benzimidazole derivative with antineuritic activity at the same time, BACE1 inhibitory activity and cell protective activity, and can penetrate the blood-brain barrier; at the same time the benzimidazole derivatives for the preparation of simple, low cost, stable structure, convenient for storage, can be used as a treating [...] of one kind of precursor compound.

Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially 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 additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.

UREA PEPTOID BORIC ACID COMPOUND, PHARMACEUTICAL COMPOSITION THEREOF, PREPARATION METHOD THEREFOR, AND USES THEREOF

The present invention provides a urea peptidomimetic boronic compound and pharmaceutical compositions thereof, their preparative methods and uses. The compounds are represented by the following formula (I).