13063-54-2

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-Corypalmine is used as a therapeutic agent for its anti-inflammatory, analgesic, and antinociceptive properties, making it suitable for the treatment of pain and inflammation-related conditions. Its unique stereochemistry ensures that the (R)-enantiomer is the biologically active form, which is crucial for its pharmacological effects.
Used in Antioxidant Applications:
(R)-(+)-Corypalmine is utilized as an antioxidant, which can help protect cells from oxidative stress and damage, potentially contributing to the prevention and treatment of various diseases associated with oxidative stress.
Used in Antitumor Applications:
(R)-(+)-Corypalmine is employed as an antitumor agent, indicating its potential to inhibit the growth of cancer cells and contribute to cancer treatment strategies.
Used in Neuroprotective Applications:
(R)-(+)-Corypalmine is used as a neuroprotective agent, suggesting its potential to protect neurons from damage and degeneration, which could be beneficial in the treatment of neurodegenerative diseases.

InChI:InChI=1/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 107538-88-5 14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine 
• 63909-29-5 3-benzyloxy-4-methoxy-β-nitrostyrene 
• 3621-38-3 Jatrorrhizine 
• 6681-15-8 jatrorrhizine hydrochloride 
• 4697-59-0 7,8-dimethoxyisochroman-3-one 
• 91421-51-1 N-<2-(3-Benzyloxy-4-methoxyphenyl)-ethyl>-(3,4-dimethoxy-2-hydroxymethyl)-phenylacetamide 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 
• 27313-88-8 o-Benzyloxy-(+/-)-corypalmine 
• 621-59-0 isovanillin 
• 1422431-45-5 6-((6-(benzyloxy)-7-methoxy-3,4-dihydroisoquinolin-1-yl)methyl)-2,3-dimethoxybenzyl acetate 
• 1131-94-8 homoisovanillic acid 
• 19626-36-9 methyl 2-(3-bromo-4-methoxyphenyl)acetate 
• 34918-57-5 methyl 3-bromo-4-hydroxyphenylacetate 

Downstream Products

• 483-14-7 tetrahydropalmatine 
• 518-90-1 3,4-dimethoxy-phthalic acid 
• 99866-19-0 4-ethoxy-5-methoxy-phthalic acid 

Relevant academic research and scientific papers

THE ABSOLUTE CONFIGURATION OF BERBERASTINE AND THALIDASTINE

Optical resolution of (+/-)-tetrahydrojatrorrhizine using (-)-O,O-di-p-toluoyl-d-tartaric acid gave rise to (+)-tetrahydrojatrorrhizine (6) of high optical purity and of known absolute configuration.Oxidation of this enantiomer with lead tetraacetate, followed by acid hydrolysis, furnished alcohols 10 and ll in a 2:1 ratio, whose relative stereochemistry was established from their nmr spectra.Iodine oxidation of the major alcohol 10 led to protoberberinium salt 14 which was found to be dextrorotatory.Since berberastine (1) and thalidastine (2) are also dextrorotatory, they must possess the same absolute configuration as 14.

UNUSUAL METHYL TRANSFER IN THE BIOSYNTHESIS OF APORPHINE AND PROTOBERBERINE ALKALOIDS

(S)-Reticuline was triply-labelled with 13C and administrered to cell cultures of Peumus boldus and Berberis stolonifera, which are sources of aporphines and protoberberines, respectively.During incorporation of the labelled precursor into alkaloids of both groups, unexpected transmethylations of the methyl groups were observed by 13C NMR spectroscopy which seem to proceed via demethylation, flux of 13C through the C-1 pool, and remethylation. Key Word Index: Peumus boldus; Berberis stolonifera; Berberidaceae; cell suspension cultures; 13C NMR; reticuline; aporphines; protoberberines; alkaloids; biosynthesis

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.

Phenolic Berbine Alkaloids: An Improved Total Synthesis of (+/-)-Corypalmine

An improved total synthesis of (+/-)-corypalmine (5) starting from 7,8-dimethoxyisochroman-3-one (1) is described.