13407-95-9

Usage

Molecular weight

369.45 g/mol

Molecular structure

A complex structure with a central isoquinoline ring system, featuring four methoxy groups attached to specific carbon atoms.

Class

Isoquinoline alkaloids

Biological activity

Potential for medicinal properties and therapeutic applications.

Pharmacological and biochemical actions

Requires further study to explore its potential.

Drug development

A potential candidate for the development of new drugs.

Position of methoxy groups

The four methoxy groups are positioned at carbons 2, 3, 10, and 11.

Hydrogen atoms

The compound has 27 hydrogen atoms.

Nitrogen atom

The compound has one nitrogen atom.

Oxygen atoms

The compound has four oxygen atoms.

Upstream product

• 16135-49-2 N-<2-(3,4-dimethoxyphenyl)-ethyl>-(4,5-dimethoxy-2-hydroxymethyl)-phenylacetamide 
• 10211-78-6 8-oxypseudopalmatine 
• 101481-10-1 5,8,13,14-tetrahydro-12-hydroxy-2,3,10,11-tetremethoxy-6H-dibenzoquinolizine 
• 106544-61-0 2-(4,5-dimethoxy-2-((trimethylsilyl)methyl)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinolinium perchlorate 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 4927-55-3 1,2-bis(3,4-dimethoxyphenyl)ethanone 
• 63490-92-6 polycarpine 
• 83392-75-0 [2-(3,4-Dimethoxy-phenyl)-ethyl]-(4,5-dimethoxy-2-trimethylsilanylmethyl-benzyl)-amine 
• 83392-72-7 (2-bromo-4,5-dimethoxybenzyl)trimethylsilane 
• 83392-73-8 4,5-dimetoxy-2-((trimethylsilyl)methyl)benzaldehyde 
• 83392-71-6 <(3,4-dimethoxyphenyl)methyl>trimethylsilane 
• 21763-07-5 6,7-Dimethoxy-1,4-dihydro-2H-isoquinoline-3-one 
• 40173-90-8 3,4-dimethoxyphenethyl bromide 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 

Downstream Products

• 57129-74-5 (+/-)-N-methylxylopinine iodide 
• 120021-26-3 3-(2-vinyl-4,5-dimethoxyphenyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 6899-65-6 (+/-)-O-methylcorytenchirine 
• 19716-66-6 pseudopalmatine 
• 52194-51-1 (+/-)-Xylopinin-trans-methiodid 

Relevant academic research and scientific papers

THE PROTOBERBERINE ALKALAOIDS OF STEPHANIA SUBEROSA

Six new protoberberines were found in Stephania suberosa root extracts: (-)-tetrahydrostephabine, (-)-stephabinamine, stephabine, 8-oxopseudopalmatine, (-)-trans-xylopinine N-oxide and (-)-cis-xylopinine N-oxide.Ten known alkaloids were also detected: (-)-tetrahydropalmatine, (-)tetrahydropalmatrubine, (-)-stepholidine, (-)-kikemanine, (-)-capaurimine, (-)-coreximine, (-)-corytenchine, (-)-discretine, pseudopalmatine and (-)-xylopinine. Key Word Index--Stephania suberosa; Menispermaceae; roots ; protoberberines; alkaloids.

2-(o-tolyl)-4,4-dimethyl-2-oxazolines - A new vehicle for facile convergent synthesis of protoberberine alkaloids

A single step synthesis of 8-oxotetrahydroprotoberberines (57-82%) by the addition of lithiated 2-(o-tolyl)-4,4-dimethyl-2-oxazolines on 3,4- dihydroisoquinolines is described.

One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds

Fused indolizidines and quinolizidines are important skeletons in a variety of natural products and pharmacologically important compounds. A one-pot tandem route from amide to fused indolizidines and quinolizidines is disclosed. This method is conducted in mild conditions and shows well tolerance of functional groups. It is also easy to be scaled up to gram scale and can be applied smoothly to the total synthesis of alkaloids such as (±)-crispine A, (±)-xylopinine, (±)-desbromoarborescidine A, (±)-harmicine and other bioactive substances.

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

Stereoselective construction of a berberine C-8 benzyl group for the synthesis of javaberine derivatives

Diastereoselective synthesis of 8-benzyltetrahydroprotoberberines was examined. Although Stevens rearrangement of N-benzylxylopinine resulted in poor yield and diastereoselectivity, benzylation of tetracyclic iminium successfully gave H8-H14 trans-benzyltetrahydroprotoberberines with high stereoselectivity.

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.

Green synthesis technology of rotundine sulfate

The invention provides a green synthesis technology of rotundine sulfate. The green synthesis technology comprises the following steps: firstly, taking pyrocatechol as a starting reactant, and carrying out esterification, acylation and nitration; then carrying out deoxygenation reduction to obtain 3,4-dimethoxyphenethylamine; then carrying out condensation on the obtained 3,4-dimethoxyphenethylamine and 2,3-dimethoxy benzaldehyde and reducing to obtain (3,4-dimethoxy)phenethyl(2,3-dimethoxy)benzylamine; finally, carrying out cyclization, reduction and sulfation on the obtained (3,4-dimethoxy)phenethyl(2,3-dimethoxy)benzylamine, so as to obtain finished-product rotundine sulfate. The invention develops a full-synthesis technology taking the pyrocatechol as a raw material, and provides an environment-friendly, low-cost and high-yield green synthesis technology for synthesizing the rotundine sulfate.

A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps

A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.

HEXAHYDRODIBENZO[A,G]QUINOLIZINE COMPOUND, PREPARATION METHOD THEREOF, PHARMACEUTICAL COMPOSITION AND USE THEREOF

The present invention relates to a novel hexahydrodibenzo[a,g]quinoline compound represented by general formula (I) and its derivatives, enantiomer, diastereoisomer, raceme and mixtures thereof, as well as pharmaceutically acceptable salts thereof. The pr

HEXAHYDRODIBENZO[A,G]QUINOLIZINE COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION AND USE THEREOF

The present invention relates to a novel hexahydrodibenzo[a,g]quinoline compound represented by general formula (I) and its derivatives, enantiomer, diastereoisomer, raceme and mixtures thereof, as well as pharmaceutically acceptable salts thereof. The present invention further relates to a method for preparing the compound, and the compound has good prevention and treatment effect on neurological diseases, especially diseases associated with dopamine receptor and 5-hydroxytryptamine receptor. The bioactivity experiment demonstrates that, the compound is expected to be developed into a novel and potent chemical entity for treating diseases associated with dopamine receptor and 5-hydroxytryptamine receptor, especially schizophrenia, Parkinson's disease, drug addiction, migraine and so on.