79809-15-7

Upstream product

• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 34918-57-5 methyl 3-bromo-4-hydroxyphenylacetate 
• 19626-36-9 methyl 2-(3-bromo-4-methoxyphenyl)acetate 
• 1131-94-8 homoisovanillic acid 
• 56201-87-7 8-hydroxy-7-methoxyisobenzofuranyltetrahydropyran-3-one 
• 4230-93-7 1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 
• 79809-14-6 N,N-dimethyl-3,4-dimethoxy-2-hydroxymethyl-benzylamine 
• 65495-21-8 N,N-dimethyl-3,4-dimethoxybenzylamine 
• 4697-59-0 7,8-dimethoxyisochroman-3-one 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 1422431-12-6 6-(2-(3,4-dimethoxyphenethylamino)-2-oxoethyl)-2,3-dimethoxyphenyl acetate 
• 2934-97-6 (+/-)-tetrahydropalmatine 

Relevant academic research and scientific papers

SYNTHESES OF 7,8-DIMETHOXY AND 7,8-METHYLENEDIOXY ISOCHROMAN-3-ONES AN EFFICIENT SYNTHESIS OF (+/-) TETRAHYDROPALMATINE AND (+) CANADINE

Efficient syntheses of the title compounds, using heteroatom directed lithiation reaction, is described.

Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors

Cocaine addiction remains a serious challenge for clinical and medical research because there is no effective pharmacological treatment. L-THP, a natural product isolated from Corydalis yanhusuo W.T. Wang, is one of the most frequently used traditional herbs to treat drug addiction in China. Our laboratory first reported that its demethylated metabolites L-ICP, L-CD, and L-CP had high affinity at dopamine D1, D2, and D5 receptors. Here we report the chemical synthesis of these metabolites and other derivatives and their binding affinities at dopamine receptors. The synthesis of these bioactive metabolites will allow further in vivo study of their potential in treating cocaine addiction.

Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D1, D2 and serotonin 5-HT1A multi-action profile

An effective and rapid method for the microwave-assisted preparation of the key intermediate for the total synthesis of tetrahydroprotoberberines (THPBs) including l-stepholidine (l-SPD) was developed. Thirty-one THPB derivatives with diverse substituents on A and D ring were synthesized, and their binding affinity to dopamine D1, D2 and serotonin 5-HT 1A and 5-HT2A receptors were determined. Compounds 18k and 18m were identified as partial agonists at the D1 receptor with Ki values of 50 and 6.3 nM, while both compounds act as D2 receptor antagonists (Ki = 305 and 145 nM, respectively) and 5-HT1A receptor full agonists (Ki = 149 and 908 nM, respectively). These two THPBs compounds exerted antipsychotic actions in animal models. Further electrophysiological studies employing single-unit recording in intact animals demonstrated that 18k-excited dopaminergic (DA) neurons are associated with its 5-HT1A receptor agonistic activity. These results suggest that these two compounds targeted to multiple neurotransmitter receptors may present novel lead drugs with new pharmacological profiles for the treatment of schizophrenia.

SYNTHETIC APPLICATION OF LITHIATION REACTIONS - XVI: SYNTHESES OF (+/-)TETRAHYDROPALMATINE, (+/-)CANADINE, (+/-)STYLOPINE AND (+/-)SINACTINE

N,N-Dimethyl-3,4-dimethoxy- and methylenedioxybenzylamines were lithiated and the organolithium intermediates treated with paraformaldehyde to give the 2-hydroxymethyl derivatives.The latter were converted to 7,8-dimethoxy- and methylenedioxyisochroman-3-ones through successive reaction with ClCOOEt, KCN and KOH.The isochromanones on condensation with homoveratrylamine or homopiperonylamine, followed by cyclisation and reduction furnished the protoberberine alkaloids.