64397-10-0

Usage

Uses

1. Used in Pharmaceutical Industry:
SIBIRICINE is used as a bioactive compound for its potential therapeutic applications. Its unique structure and natural origin make it a promising candidate for the development of new drugs and treatments.
2. Used in Research and Development:
SIBIRICINE serves as a valuable research tool for scientists studying the chemical properties and pharmacological effects of spiro base compounds. Its structure and potential applications can provide insights into the development of novel therapeutic agents.
3. Used in Drug Discovery:
SIBIRICINE is used as a lead compound in drug discovery, where its unique properties and potential pharmacological activities can be further explored and optimized for specific therapeutic targets.
4. Used in Traditional Medicine:
As a constituent of Corydalis sibirica, SIBIRICINE may be used in traditional medicine practices, where the plant is known for its analgesic and anti-inflammatory properties.
5. Used in Neuroprotective Applications:
Given its potential pharmacological properties, SIBIRICINE could be investigated for its neuroprotective effects, particularly in the context of neurodegenerative diseases.
6. Used in Antidepressant Applications:
SIBIRICINE may also be explored for its potential antidepressant effects, as some alkaloids have been shown to modulate mood and alleviate depressive symptoms.
7. Used in Pain Management:
Considering the analgesic properties of Corydalis sibirica, SIBIRICINE could be investigated for its potential use in pain management, particularly for chronic pain conditions.
8. Used in Anticancer Applications:
Similar to other alkaloids, SIBIRICINE may be studied for its potential anticancer properties, exploring its ability to target cancer cells and inhibit tumor growth.
9. Used in Drug Delivery Systems:
SIBIRICINE could be incorporated into novel drug delivery systems to improve its bioavailability, targeting, and therapeutic outcomes in various medical applications.
10. Used in Toxicology Studies:
As a naturally occurring compound, SIBIRICINE may be used in toxicology studies to understand its safety profile and potential side effects, ensuring its safe use in medical applications.

References

Manske et al., Can. J. Chem., 47, 3585 (1969)

Upstream product

• 64361-54-2 dehydrobicuculline 
• 494-55-3 N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 71622-48-5 C₂₀H₁₅NO₆ 
• 84229-91-4 7,8,6',8'-tetrahydro-6H-(7'rN)-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6't,8'c-diol 
• 62-31-7 dopamine hydrochloride 
• 50506-19-9 2'-formyl-8t-hydroxy-6',7'-bis-methoxycarbonyloxy-3',4'-dihydro-8H,2'H-(7rN)-spiro[indeno[4,5-d][1,3]dioxole-7,1'-isoquinolin]-6-one 
• 50506-20-2 6-formyl-8't-hydroxy-7,8-dihydro-6H,8'H-(7'rN)-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxol]-6'-one 
• 64361-52-0 8't-hydroxy-7,8-dihydro-6H,8'H-(7'rN)-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxol]-6'-one 
• 64395-08-0 8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxole-6-carboxylic acid (2-benzo[1,3]dioxol-5-yl-ethyl)-methyl-amide 
• 71622-64-5 8-bromo-8H-indeno[4,5-d][1,3]dioxole-6,7-dione 
• 99132-03-3 C₂₀H₁₅NO₆ 
• 99132-04-4 C₂₁H₁₉NO₇ 
• 96860-74-1 Protoberberine 
• 75267-17-3 5-Formyl-benzo[1,3]dioxole-4-carboxylic acid ethyl ester 

Downstream Products

• 24181-64-4 severzinine 
• 24181-64-4 (+/-)-sewercinine 

Relevant academic research and scientific papers

γ-Alkoxylactones as Autounmasking Synthons for a One-step Construction of 1,3-Oxygenated Cyclopentanes. Synthesis of Fredericamycin A Core and Spirobenzylisoquinoline Alkaloids

Reaction of γ-alkoxyphthalide 7a with 3-indenyllithium leads to fredericamycin A core compound 5, whereas condensation of methylenedioxyphthalide 7b or 8 with lithiated N-methyltetrahydroisoquinoline-BF3 complex 9 affords spirobenzylisoquinoline alkaloids raddeanine 12, corydaine 13 and yenhusomidine 13.

A NOVEL AND HIGHLY STEREOSELECTIVE SYNTHESIS OF (+/-)-SIBIRICINE

A novel and stereoselective synthesis of (+/-)-sibiricine (1), a spirobenzylisoquinoline alkaloid, from the corresponding protoberberine (3) was developed using photo-oxygenation and photo-isomerization.

A TOTAL SYNTHESIS OF (+/-)-CORYDAINE FROM COPTISINE

Regioselective protection of C8-hydroxy of the spiro-diol (6b) derived from coptisine (1b), followed by oxidation of C13-hydroxy afforded the keto-oxazolidine (8b) which was treated with sodium cyanoborohydride to provide (+/-)-corydaine (5b) in an excellent yield.