7461-02-1

Basic information

• Product Name: STYLOPINE, (-)-(RG)(CALL)
• Synonyms: STYLOPINE, (-)-(RG)(CALL);Coptisine, tetrahydro-;Nsc404529
• CAS NO: 7461-02-1
• Molecular Formula: C₁₉H₁₇NO₄
• Molecular Weight: 323.34258
• Product Categories: Alkaloids
• Mol File: 7461-02-1.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 466.6°Cat760mmHg
• Flash Point: 142.5°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 7E-09mmHg at 25°C
• Refractive Index: 1.722
• CAS DataBase Reference: STYLOPINE, (-)-(RG)(CALL)(CAS DataBase Reference)
• NIST Chemistry Reference: STYLOPINE, (-)-(RG)(CALL)(7461-02-1)
• EPA Substance Registry System: STYLOPINE, (-)-(RG)(CALL)(7461-02-1)

Safety Data

• Hazardous Substances Data: 7461-02-1(Hazardous Substances Data)

Usage

General Description

Stylopine, also known as (-)-(RG)(CALL), is an alkaloid chemical compound found in various plant species such as Stylophorum diphyllum and Chelidonium majus. It is a bioactive compound with potential pharmaceutical and therapeutic properties, including anti-inflammatory and analgesic effects. Research has shown that stylopine may also have anticancer properties and could potentially be useful in the development of new drugs for the treatment of various diseases. Additionally, it has been studied for its potential use in the treatment of neurodegenerative disorders and as a natural antifungal agent. Overall, stylopine is a promising chemical compound with a wide range of potential applications in medicine and pharmacology.

InChI:InChI=1/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2

Upstream product

• 41431-72-5 rac-7-methyl-2,3;9,10-bis-methylenedioxy-berbinium; chloride 
• 65826-53-1 14-bromo-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline 
• 6020-18-4 coptisine chloride 
• 113557-44-1 7,8-methylenedioxy-2-(3,4-methylenedioxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-3-one 
• 87167-71-3 N-<2-(3,4-methylenedioxyphenyl)ethyl>(3,4-methylenedioxy-2-hydroxymethyl)-phenylacetamide 
• 106544-66-5 2-(2,3-(methylenedioxy)-6-((trimethylsilyl)methyl)benzyl)-6,7-(methylenedioxy)-3,4-dihydroisoquinolinium perchlorate 
• 76177-42-9 (±)-8-oxostylopine 
• 75-09-2 dichloromethane 
• 53777-78-9 Dihydrocoptisine 
• 53777-79-0 N-methyl-13,14-dehydrostylopinium chloride 
• 130-86-9 protopine 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 63375-82-6 2-(6-bromo-benzo[1,3]dioxol-5-yl)-ethylamine 
• 113557-36-1 2-bromo-4,5-methylenedioxy-N-2,3-methylenedioxyphenethylamine 

Downstream Products

• 130-86-9 protopine 
• 49870-84-0 corydamine 
• 6020-18-4 coptisine chloride 

Relevant articles and documents

A unified total synthesis of benzo[: D] [1,3]dioxole-type benzylisoquinoline alkaloids of aporphines, coptisines, and dibenzopyrrocolines

The first total synthesis of (S)-(+)-ovigerine, (S)-(+)-N-formylovigerine, and (6aS,6a'S)-(+)-ovigeridimerine of aporphine alkaloids with a benzo[d][1,3]dioxole structure feature was established. The strategy was based upon the well-known Pd-catalyzed arylation to set the aporphine framework, and Noyori asymmetric hydrogenation followed by diastereoselective resolution to achieve excellent enantioselectivity. By slightly modifying the total synthetic route and strategically combining it with a aza-Michael addition, Bischler-Napieralski reaction and N-arylation, this methodology was also applied to the total syntheses of benzo[d][1,3]dioxole-type benzylisoquinoline alkaloids of coptisines and dibenzopyrrocolines, including two impatiens, tetrahydrocoptisine, and quaternary coptisine bromide of coptisines and two dibenzopyrrocoline analogues, with the syntheses of all of these target compounds being efficient. Among the nine synthesized compounds, the total syntheses of the three aporphines and the two impatiens, all with ee values of greater than 99%, were reported for the first time. This work also represents the first unification of synthetic routes for the total synthesis of benzo[d][1,3]dioxole-type aporphines, coptisines, and dibenzopyrrocolines. This journal is

Berberine-based derivative and preparation method thereof, pharmaceutical composition, and antitumor uses of berberine-based derivative and pharmaceutical composition

The invention discloses a berberine-based derivative and a synthesis method thereof, and applications of the berberine-based derivative in preparation of products for prevention, alleviation and/or treatment of tumors, wherein the berberine-based derivative is a 12-aminotetrahydroberberine-based derivative represented by a general formula I or a physiologically acceptable salt thereof, a 12-N,N-disubstituted aminotetrahydroberberine-based derivative or a physiologically acceptable salt thereof, a 12-amino berberine quaternary ammonium salt derivative represented by a general formula II or a physiologically acceptable salt thereof, and a 12-N,N-disubstituted amino baterine quaternary ammonium salt derivative or a physiologically acceptable salt thereof. According to the present invention, the solubility of the berberine-based derivative is significantly improved compared to the raw material chlorinated berberine quaternary ammonium salt compound; and the obtained berberine-based derivative can provide inhibition activity on the growth of tumor cell lines, and can be used for preparing products for prevention, alleviation and/or treatment of tumors, wherein the action intensity of the berberine-based derivative is significantly higher than the berberine quaternary ammonium salt raw material, or is comparable to the positive control drug, or is higher than the positive control. The general formulas I and II are defined in the specification.

Synthesis and Structure-Activity Relationships of Quaternary Coptisine Derivatives as Potential Anti-ulcerative Colitis Agents

Thirty quaternary coptisine derivatives from a synthesized library were found to activate the in vitro transcription of x-box-binding protein 1 (XBP1). Among these, the dihydrocoptisines were demonstrated by in vitro XBP1 transcriptional activity assays and animal experiments to be much more active anti-ulcerative colitis (UC) agents than quaternary coptisines, tetrahydrocoptisines, and the positive control. Unsubstituted dihydrocoptisine exhibited more significant anti-UC efficacy than dihydrocoptisines substituted at the C-8 or C-13 position. The EC50 value of dihydrocoptisine for XBP1 transcriptional activation was 2.25 nM. Dihydrocoptisine exhibited a significant dose-effect relationship, as indicated by biomarkers in in vitro and in vivo experiments. According to this study, the starting material's reductive states and the substitution patterns of the dihydrocoptisines were determined to be the critical parameters for modulating their anti-UC efficacy, and the dihydrocoptisine skeleton was designated as the key pharmacophore. The synthesized dihydrocoptisine is a promising lead for developing anti-UC drugs.