34162-11-3

Usage

InChI:InChI=1/C11H14ClNO2/c1-15-10-5-3-2-4-9(10)6-7-13-11(14)8-12/h2-5H,6-8H2,1H3,(H,13,14)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 2045-79-6 o-methoxy-2-phenylethylamine 
• 79-11-8 chloroacetic acid 

Downstream Products

• 259206-62-7 2-acetyl-5-methoxy-1-[N-methyl-(2-phenylethyl)amino]methyl-1,2,3,4-tetrahydroisoquinoline 
• 259206-60-5 5-methoxy-1-[N-methyl-(2-phenylethyl)amino]methyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

3-aroylmethylene-2,3,6,7-tetrahydro-1 H -pyrazino[2,1- a ]isoquinolin-4(11b H)-ones as potent Nrf2/ARE inducers in human cancer cells and AOM-DSS treated mice

Nrf2-mediated activation of ARE regulates expression of cytoprotective enzymes against oxidative stress, inflammation, and carcinogenesis. We have discovered a novel structure (1) as an ARE inducer via luciferase reporter assay to screen the in-house data

Synthesis of a small library of phenylalkylamide derivatives as melatoninergic ligands for human mt1 and MT2 receptors

Focused small libraries of melatonin receptor ligands from arylalkylamine derivatives were synthesised by combinatorial chemistry using the mix and split method in the solid phase. A library of 108 compounds was then synthesised from 12 arylalkyl amines and nine carboxylic acids. The compound mixtures were evaluated on chicken brain melatonin and recombinant human mt1 and MT2 receptors. Deconvolution of the most potent mixture demonstrated the superiority of 3-methoxy and 2,5-dimethoxy substitution on the phenyl ring with isopropyl, propyl and ethyl amido chains. Several compounds with nanomolar affinity for human melatonin receptors were obtained. (C) 2000 Elsevier Science Ltd.

Synthesis, conformational analysis and antinociceptive activity of 1-[N- methyl-(2-phenylethyl)amino]methyl-1,2,3,4-tetrahydroisoquinoline derivatives

New derivatives of 1-[N-methyl-(2-phenylethyl)amino]methyl-1,2,3,4- tetrahydroisoquinoline were synthesized. The antinociceptive activity of the compounds, determined by the mouse tail-flick test, showed that the introduction of a hydroxy substituent in p

Substituted 1-(aminomethyl)-2-(arylacetyl)-1,2,3,4- tetrahydroisoquinolines: A novel class of very potent antinociceptive agents with varying degrees of selectivity for κ and μ opioid receptors

This study describes the synthesis of a series of novel substituted 1- (aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinolines, and discusses their structure-activity relationships (SARs) using binding affinity for opioid receptors and antinociceptive potency as the indices of biological activity. The introduction of a hydroxy substituent in position 5 of the isoquinoline nucleus generated a compound, 40, which is 2 times more potent than the previously disclosed unsubstituted analogue 39 in mouse models of antinociception. A QSAR analysis of the 5-substitution clearly demonstrates that antinociceptive activity is inversely associated with the lipophilicity of the substituents. The substituted compounds described herein are less selective for the κ opioid receptors than the unsubstituted isoquinoline 39. For example, the 5-hydroxy-substituted compound 59 shows high affinity for κ opioid receptors (K(i) κ = 0.09 nM) and a (K(i) μ/K(i) κ ratio of only 5. However, a multiple linear regression analysis demonstrates a lack of correlation between antinociceptive activity and affinity for the μ opioid receptor. On the other hand, the correlation between binding affinity to κ opioid receptor and antinociceptive activity was statistically significant.