6957-27-3

Usage

Uses

Used in Pharmaceutical Industry:
1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline is used as an impurity in Papaverine, a smooth muscle relaxant and vasodilator found in opium. Its presence in Papaverine may contribute to the overall pharmacological effects of the drug, particularly in its use as a vasodilator for cerebral circulation.
Used in Chemical Research:
As a member of the isoquinoline family, 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline can be utilized in chemical research for the development of new compounds with potential therapeutic applications. Its unique structure may offer insights into the design of novel drugs targeting specific biological pathways or receptors.
Used in Drug Synthesis:
1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline may also serve as a key intermediate in the synthesis of other pharmaceutically relevant molecules. Its presence in the synthesis process could lead to the development of new drugs with improved efficacy, safety, or pharmacokinetic properties.

InChI:InChI=1/C20H23NO4.BrH/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16;/h5-6,10-12H,7-9H2,1-4H3;1H

Upstream product

• 27160-08-3 2-(3,4-dimethoxyphenyl)-ethylchloride 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 796074-04-9 (2,3-dimethoxy-phenyl)-acetic acid-(2,3-dimethoxy-phenethylamide) 
• 72527-19-6 2-(3,4-dimethoxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]thioacetamide 
• 96625-09-1 {1-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl}-carbamic acid ethyl ester 
• 13074-31-2 Tetrahydropapaverine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 863132-09-6 2-[2-(3,4-dimethoxy-phenylethynyl)-4,5-dimethoxy-phenyl]-ethylamine 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 14301-36-1 N-[2-(3,4-dimethoxyphenyl)ethyl]formamide 

Downstream Products

• 82044-12-0 1-{1-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl}-2-phenyl-ethanone 
• 82044-11-9 1-{1-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl}-2-phenyl-ethanone 
• 68346-10-1 2'-hydroxymethyl-3,4-dihydropapaverine 
• 96625-09-1 {1-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl}-carbamic acid ethyl ester 
• 81165-68-6 C₅₀H₆₆N₂O₈⁽²⁺⁾*2I^(1-) 
• 154013-05-5 (E)-1-<(3,4-Dimethoxyphenyl)methylene>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 61348-95-6 (Z)-1-<(3,4-Dimethoxyphenyl)methylene>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 104621-37-6 (Z)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 104621-38-7 (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 104621-47-8 (E)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 17366-51-7 (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 81305-66-0 5,6,7,8,13,13a-hexahydro-13a-(3',4'-dimethoxybenzyl)-2,3-dimethoxy-8-oxoisoquinolo<1,2-b>quinazoline 
• 104621-39-8 (Z)-2-(p-Bromobenzoyl)-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 82064-37-7 1-(3,4-Dimethoxy-phenyl)-1-[6,7-dimethoxy-2-phenylacetyl-3,4-dihydro-2H-isoquinolin-(1E)-ylidene]-3-phenyl-propan-2-one 

Relevant academic research and scientific papers

COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING NASH, NAFLD, AND OBESITY

The present technology relates to methods of treating NASH, NAFLD and/or obesity using compounds of Formulas I, II, III, IV, V, and/or VI. The methods include administering to a subject suffering from one or more of non-alcoholic steatohepatitis (NASH), non- alcoholic fatty liver disease (NAFLD) and/or obesity a therapeutically effective amount of such a compound

Preparation method of papaverine

The invention discloses a preparation method of papaverine. The invention provides a preparation method of papaverine, which comprises the following steps: (1) in a solvent, in the presence of a cyclization agent, carrying out cyclization reaction as shown in the specification on a compound as shown in a formula I to obtain a compound as shown in a formula II; and (2) in a solvent, in the presence of a dehydrogenation catalyst, carrying out dehydrogenation reaction as shown in the specification on the compound as shown in the formula II to obtain papaverine. The compound as shown in the formula II prepared in the step (1) is directly used in the step (2) without being purified. The method is simple in process, easy to operate, low in cost and suitable for industrial production, and the product is high in yield and purity.

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.

One-Pot Synthesis of Papaverine Hydrochloride and Identification of Impurities

Abstract: A one-pot synthesis of papaverine hydrochloride with 99.6% purity was performed using xylene as solvent for the entire process. The critical parameters of each step, as well as the impurities generated, were identified. The overall yield was improved to 63%. The proposed synthetic procedure is suitable for industrial production.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.

Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C-N and C-C Bond Formation

A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus PIII/PV redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successive C-N and C-C bond-forming dehydration events via the serial action of a catalytic bromophosphonium intermediate. These results demonstrate the capacity of PIII/PV redox catalysis to enable iterative redox-neutral transformations in complement to the common reductive driving force of the PIII/PV couple.

Oxidative route to pyrroloisoquinoline-2,3-dione

We herein report an efficient constructive method for synthesis of structurally important Pyrroloisoquinoline-2,3-dione from dihydroisoquinoline through oxidative cyclisation. Process is optimised to give best efficiency at gram scale and laborious purification techniques such as column chromatography or recrystallisation were avoided in all steps further featuring uniqueness of this method as compared to the available literature.

Domino Reactions of 1-Aroyl-3,4-dihydroisoquinolines with α,β-Unsaturated Aldehydes

An efficient synthesis of pyrrolo[2,1- a ]isoquinolines by a domino reaction from a variety of 3,4-dihydropyrrolo[2,1- a ]isoquinolines and α,β-unsaturated aldehydes in the absence of catalyst in good yields under microwave irradiation, is reported.

Preparation methods of papaverine and papaverine hydrochloride

The invention discloses a preparation method of papaverine. The preparation method comprises 1, dissolving 3, 4-dihydropapaverine hydrochloride in water and adjusting pH of the solution to greater than 7, 2, through trimethylbenzene, carrying out extraction on the aqueous solution obtained through the step 1, and 3, adding a dehydrogenation reaction catalyst into the obtained organic phase, carrying out a dehydrogenation reaction process at a temperature of 50-180 DEG C and then treating the product to obtain papaverine. The invention also discloses a method for preparing papaverine hydrochloride from the papaverine. Through use of trimethylbenzene as a dehydrogenation reaction solvent, a dehydrogenation reaction temperature is reduced, peroxide production is avoided and production safety is greatly improved. The preparation method realizes recycle of trimethylbenzene and reduces a production cost of papaverine or papaverine hydrochloride.

Effect of 1-Substitution on Tetrahydroisoquinolines as Selective Antagonists for the Orexin-1 Receptor

Selective blockade of the orexin-1 receptor (OX1) has been suggested as a potential approach to drug addiction therapy because of its role in modulating the brain's reward system. We have recently reported a series of tetrahydroisoquinoline-based OX1 selective antagonists. Aimed at elucidating structure-activity relationship requirements in other regions of the molecule and further enhancing OX1 potency and selectivity, we have designed and synthesized a series of analogues bearing a variety of substituents at the 1-position of the tetrahydroisoquinoline. The results show that an optimally substituted benzyl group is required for activity at the OX1 receptor. Several compounds with improved potency and/or selectivity have been identified. When combined with structural modifications that were previously found to improve selectivity, we have identified compound 73 (RTIOX-251) with an apparent dissociation constant (Ke) of 16.1 nM at the OX1 receptor and >620-fold selectivity over the OX2 receptor. In vivo, compound 73 was shown to block the development of locomotor sensitization to cocaine in rats. (Chemical Equation Presented).