32728-75-9

Basic information

• Product Name: Cavidine
• Synonyms: Cavidine
• CAS NO: 32728-75-9
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.416
• Mol File: 32728-75-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 463.6 °C at 760 mmHg
• Flash Point: 133.8 °C
• Appearance: /
• Density: 1.3 g/cm³
• Vapor Pressure: 8.96E-09mmHg at 25°C
• Refractive Index: 1.643
• PKA: 6.57±0.40(Predicted)
• CAS DataBase Reference: Cavidine(CAS DataBase Reference)
• NIST Chemistry Reference: Cavidine(32728-75-9)
• EPA Substance Registry System: Cavidine(32728-75-9)

Safety Data

• Hazardous Substances Data: 32728-75-9(Hazardous Substances Data)

Usage

General Description

Cavidine is a benzylisoquinoline alkaloid found in several plant species, including the Corydalis yanhusuo plant. It has been traditionally used in Chinese medicine for its anti-inflammatory, analgesic, and sedative properties. Cavidine has also shown potential in inhibiting the growth of cancer cells and inducing apoptosis in various cancer cell lines. Additionally, it has been studied for its potential in treating cardiovascular diseases and neurological disorders. Cavidine is thought to exert its pharmacological effects by modulating the activity of various molecular targets, including ion channels and signaling pathways. Its diverse medicinal properties make it a promising candidate for further research and potential therapeutic applications.

InChI:InChI=1/C21H23NO4/c1-12-14-4-5-17-21(26-11-25-17)16(14)10-22-7-6-13-8-18(23-2)19(24-3)9-15(13)20(12)22/h4-5,8-9,12,20H,6-7,10-11H2,1-3H3/t12-,20+/m0/s1

Upstream product

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• 79055-77-9 (+)-trans-2,3-Dimethoxy-8-oxo-9,10-(methylenedioxy)-13-carboxytetrahydroprotoberberine 
• 79055-79-1 (+)-trans-2,3-Dimethoxy-8-oxo-9,10-(methylenedioxy)-13-(methoxycarbonyl)tetrahydroprotoberberine 
• 79082-09-0 (+)-cis-2,3-Dimethoxy-8-oxo-9,10-(methylenedioxy)-13-(hydroxymethyl)tetrahydroprotoberberine 
• 79055-81-5 (+)-cis-2,3-Dimethoxy-8-oxo-9,10-(methylenedioxy)-13-(methoxycarbonyl)tetrahydroprotoberberine 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 72744-54-8 5-bromo-benzo[1,3]dioxole-4-carbaldehyde 

Relevant articles and documents

Three-Step Catalytic Asymmetric Total Syntheses of 13-Methyltetrahydroprotoberberine Alkaloids

(S,R)-N-PINAP was identified to be the chiral ligand for highly enantioselective CuI-catalyzed reaction of tetrahydroisoquinolines (THIQs), alkynes, and 2-bromobenzaldehyde derivatives. This enables us to accomplish the first asymmetric total synthesis of 12 natural 13-methyltetrahydroprotoberberine (13-MeTHPB) alkaloids in only three catalytic steps with 47-64% overall yields. In addition, the Pd-catalyzed reductive Heck cyclization was successfully extended to three Pd-catalyzed domino reactions (Heck/Suzuki, Heck/Sonogashira, and Heck/Heck), which greatly expands the synthetic utility of this catalytic strategy and allows expeditious access to 13-substituted tetrahydroprotoberberines for further bioactivity evaluation.

Absolute Configurations of the cis- and trans-13-Methyltetrahydroprotoberberines. Total Synthesis of (+)-Thalictricavine, (+)-Canadine, (+/-)-, (-)-, and (+)-Thalictrifoline, and (+/-)-, (-)-, and (+)-Cavidine

The tetrahydroprotoberberine alkaloids (+)-thalictricavine and (+)-canadine have been synthesized from an optically resolved (+)-13-carboxy-7,8,13,14-tetrahydro-9-oxoprotoberberine .This establishes the absolute configuration of (+)-thalictricavine as 13S,14R. (+)-Thalictrifoline and (+)-cavidine have also been prepared from a common intermediate, (+)-32, whose absolute configuration was established by correlation with (+)-26.This determines the absolute configuration of (+)-thalictrifoline as 13R,14R, of (+)-corydalic acid methyl ester (22) as 3R,4R, and of the protopine (+)-corycavine (20) as 13R.