608141-10-2

Basic information

• Product Name: 6,7-dimethoxy-1-(3'-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 6,7-dimethoxy-1-(3'-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 608141-10-2
• Molecular Weight: 311.381
• Mol File: 608141-10-2.mol

Chemical Properties

• CAS DataBase Reference: 6,7-dimethoxy-1-(3'-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dimethoxy-1-(3'-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline(608141-10-2)
• EPA Substance Registry System: 6,7-dimethoxy-1-(3'-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline(608141-10-2)

Safety Data

• Hazardous Substances Data: 608141-10-2(Hazardous Substances Data)

Upstream product

• 67237-63-2 N-(3,4-dimethoxyphenylethyl)-β-(3'-methoxyphenyl)acetamide 
• 1798-09-0 m-methoxyphenylacetic acid 
• 6834-42-0 3-methoxyphenylacetic acid chloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 4230-93-7 1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 20359-11-9 (6,7-dimethoxyisoquinolin-1-yl)(3-methoxyphenyl)methanone 
• 136657-32-4 (S)-(-)-(3-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 1443828-62-3 ((3-bromophenyl)(6,7-dimethoxy-1-(3-methoxybenzyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone) 
• 1443828-61-2 ((3-chlorophenyl)(6,7-dimethoxy-1-(3-methoxybenzyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone) 
• 109808-84-6 1-(3-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1126908-81-3 1-[dichloro-(3-methoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline 

Relevant articles and documents

Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

A mild, efficient and eco-friendly method for the oxidation of 1-Bn-DHIQs to 1-Bz-DHIQs without concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs is very important for the syntheses of 1-Bz-DHIQ alkaloids and analogues. In this article, we developed a novel Cu(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to the C-1 positions of various 1-Bn-DHIQs. It was observed that when 0.2 equiv. of Cu(OAc)2·2H2O was used as the catalyst, 3.0 equiv. of AcOH was used as the additive and air (O2) was used as a clean oxidant, various 1-Bn-DHIQs could be efficiently oxidized to corresponding 1-Bz-DHIQs at 25 °C in DMSO. Especially, almost no concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs was observed during the above reaction. In addition, this method was successfully applied in the first total synthesis of the alkaloid canelillinoxine.

2,3,9- and 2,3,11-Trisubstituted tetrahydroprotoberberines as D2 dopaminergic ligands

Dopamine-mediated neurotransmission plays an important role in relevant psychiatric and neurological disorders. Nowadays, there is an enormous interest in the development of new dopamine receptors (DR) acting drugs as potential new targets for the treatment of schizophrenia or Parkinson's disease. Previous studies have revealed that isoquinoline compounds such as tetrahydroisoquinolines (THIQs) and tetrahydroprotoberberines (THPBs) can behave as selective D2 dopaminergic alkaloids since they share structural similarities with dopamine. In the present study we have synthesized eleven 2,3,9- and 2,3,11-trisubstituted THPB compounds (six of them are described for the first time) and evaluated their potential dopaminergic activity. Binding studies on rat striatal membranes were used to evaluate their affinity and selectivity towards D1 and D2 DR and establish the structure-activity relationship (SAR) as dopaminergic agents. In general, all the tested THPBs with protected phenolic hydroxyls showed a lower affinity for D1 and D2 DR than their corresponding homologues with free hydroxyl groups. In previous studies in which dopaminergic affinity of 1-benzyl-THIQs (BTHIQs) was evaluated, the presence of a Cl into the A-ring resulted in increased affinity and selectivity towards D2 DR. This is in contrast with the current study since the existence of a chlorine atom into the A-ring of the THPBs caused increased affinity for D1 DR but dramatically reduced the selectivity for D2 DR. An OH group in position 9 of the THPB (9f) resulted in a higher affinity for DR than its homologue with an OH group in position 11 (9e) (250 fold for D2 DR). None of the compounds showed any cytotoxicity in freshly isolated human neutrophils. A molecular modelling study of three representative THPBs was carried out. The combination of MD simulations with DFT calculations provided a clear picture of the ligand binding interactions from a structural and energetic point of view. Therefore, it is likely that compound 9d (2,3,9-trihydroxy-THPB) behave as D2 DR agonist since serine residues cluster are crucial for agonist binding and receptor activation.

Synthesis of 8-oxoberbines and related benzolactams by Pd(OAc) 2-catalyzed direct aromatic carbonylation

A variety of alkoxy-substituted benzolactams with a berbine or yohimbane skeleton were prepared from 1-benzyl-1,2,3,4-tetrahydroisoquinolines or 1-benzyl-1,2,3,4-tetrahydro-β-carbolines by a phosphine-free Pd(II)-catalyzed direct aromatic carbonylation in a Pd(OAc)2-Cu(OAc) 2 catalytic system. The site selectivity was compared with that of the carbonylation with Pd(OAc)2 or Pd(OAc)2·2 PPh3, respectively.

Synthesis and structure activity relationship of tetrahydroisoquinoline- based potentiators of GluN2C and GluN2D containing N-Methyl-D-aspartate receptors

We describe here the synthesis and evaluation of a series of tetrahydroisoquinolines that show subunit-selective potentiation of NMDA receptors containing the GluN2C or GluN2D subunits. Bischler-Napieralski conditions were employed in the key step for the

Design, synthesis, and pharmacological evaluation of novel tetrahydroprotoberberine derivatives: Selective inhibitors of dopamine D 1 receptor

A series of new tetrahydroprotoberberine (THPB) derivatives were designed, synthesized, and tested for their binding affinity towards dopamine (D 1 and D2) and serotonin (5-HT1A and 5-HT 2A) receptors. Many of the THPB compounds exhibited high binding affinity and activity at the dopamine D1 receptor, as well as high selectivity for the D1 receptor over the D2, 5-HT 1A, and 5-HT2A receptors. Among these, compound 19c exhibited a promising D1 receptor binding affinity (Ki = 2.53 nM) and remarkable selectivity versus D2R (inhibition = 81.87%), 5-HT1AR (inhibition = 61.70%), and 5-HT2AR (inhibition = 24.96%). Compared with l-(S)-stepholidine (l-SPD) (D1 Ki = 6.23 nM, D2 Ki = 56.17 nM), compound 19c showed better binding affinity for the D1 receptor (2.5-fold higher) and excellent D2/D1 selectivity. Functional assays found compounds 18j, 18k, and 19c are pure D1 receptor antagonists. These results indicate that removing the C10 hydroxy group and introducing a methoxy group at C11 of the pharmacophore of l-SPD can reverse the function of THPB compounds at the D1 receptor. These results are in accord with molecular docking studies.

New synthesis of 1-[(3,4-dimethoxyphenyl)methoxymethyl]-6,7-dimethoxyisoquinoline (setigerine), a naturally occurring alkaloid, and some derivatives of papaverine

A novel and improved synthetic route for the preparation of the new alkaloid setigerine, isolated from Papaver setigerum DC, and some new 3,4-dihydropapaverine and papaverine derivatives is reported. This method is based on the side chain chlorination of 1-benzyl-3,4-dihydroisoquinolines using N-chlorosuccinimide (NCS) and subsequent reaction with sodium methoxide in methanol to give the corresponding isoquinolines.

Antiplatelet activity of synthetic pyrrolo-benzylisoquinolines

Pyrrolo-benzylisoquinolines were prepared as target compounds and their antiplatelet aggregation activity, adreno-receptor affinity, and cytotoxicity were screened. Compounds 1d-9d showed specific antiplatelet aggregation activity induced by arachidonic acid and collagen. Among them, 8d and 9d exhibited better activity than the reference drug, aspirin and 9d also showed inhibition of platelet aggregation by all four inducers.