41823-67-0

Usage

InChI:InChI=1/C20H22BrNO4.ClH/c1-23-17-8-12-5-6-22-16(14(12)10-19(17)25-3)7-13-9-18(24-2)20(26-4)11-15(13)21;/h8-11H,5-7H2,1-4H3;1H

Upstream product

• 22185-91-7 2-(2-Bromo-4,5-dimethoxyphenyl)-N-<2-(3,4-dimethoxyphenyl)-ethyl>-acetamide 
• 4230-93-7 3,4-dimethoxynitrostyrene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 4697-57-8 methyl 2-(2-bromo-4,5-dimethoxyphenyl)acetate 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 4697-62-5 6-bromohomoveratric acid 
• 6831-57-8 2-bromo-4,5-dimethoxyphenylacetic acid chloride 

Downstream Products

• 80873-61-6 1-(2-bromo-4,5-dimethoxybenzoyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 81165-40-4 3-[1-(2-Bromo-4,5-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 2-{3-[1-(2-bromo-4,5-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-ethyl ester; compound with oxalic acid 
• 64229-12-5 C₅₀H₆₄Br₂N₂O₁₂⁽²⁺⁾*2CH₃O₃S^(1-) 
• 475-81-0 glaucine 
• 5574-24-3 oxoglaucine 
• 60372-14-7 1-(2-Bromo-4,5-dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 
• 59444-59-6 (+/-)-1-(2-bromo-4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 10211-78-6 8-oxypseudopalmatine 
• 20345-69-1 3,4-dihydropapaveraldine 
• 80041-82-3 1-(2-Bromo-4,5-dimethoxy-phenyl)-8,9-dimethoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-2,3-dione 

Relevant academic research and scientific papers

In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5-HT2 and α1 receptors

Compounds with activity at serotonin (5-hydroxytryptamine) 5-HT2 and α1 adrenergic receptors have potential for the treatment of central nervous system disorders, drug addiction or overdose. Isolaureline, dicentrine and glaucine enantiomers were synthesized, and their in vitro functional activities at human 5-HT2 and adrenergic α1 receptor subtypes were evaluated. The enantiomers of isolaureline and dicentrine acted as antagonists at 5-HT2 and α1 receptors with (R)-isolaureline showing the greatest potency (pKb?=?8.14 at the 5-HT2C receptor). Both (R)- and (S)-glaucine also antagonized α1 receptors, but they behaved very differently to the other compounds at 5-HT2 receptors: (S)-glaucine acted as a partial agonist at all three 5-HT2 receptor subtypes, whereas (R)-glaucine appeared to act as a positive allosteric modulator at the 5-HT2A receptor.

Enantioselective synthesis and anti-parasitic properties of aporphine natural products

Chagas disease and visceral leishmaniasis are neglected protozoan diseases with significant impact in developing countries. Due to the limited number and toxicity of current therapies, new drug leads are urgently needed. In this work, four aporphine natural products were synthesized using an enantioselective, modular and convergent strategy, comprising eight steps in the longest linear sequence; key steps included Bischler-Napieralski cyclization/Noyori asymmetric reduction to construct the tetrahydroisoquinolines, and palladium-catalyzed arylation to close the C ring. Norglaucine, nordicentrine and dicentrine showed promising bioactivity against T. cruzi and L. infantum, suggesting potential for further development of these scaffolds as antiparasitic agents.

Discovery of Aporphine Analogues as Potential Antiplatelet and Antioxidant Agents: Design, Synthesis, Structure–Activity Relationships, Biological Evaluations, and in silico Molecular Docking Studies

To explore the potential of aporphine alkaloids, a novel series of functionalized aporphine analogues with alkoxy (OCH3, OC2H5, OC3H7) functional groups at C1/C2 of ring A and an acyl (COCH3/sub

Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams

Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright

The palladium-catalyzed preparation of condensed tetracyclic heterocycles and their application to the synthesis of rac-mangochinine

Dihydroisoquinoline derivatives and their analogues, prepared by the Bischler-Napieralsky reaction, were converted to their indole-fused derivatives. Scope and limitations of the palladium-catalyzed reaction, proceeding through the tautomeric enamine forms of these compounds, were studied and the process was extended to the preparation of racemic mangochinine. Georg Thieme Verlag Stuttgart.