20267-87-2

Basic information

• Product Name: CHELIDONINE MONOHYDRATE*
• Synonyms: CHELIDONINE MONOHYDRATE*;(+/-)-Chelidonine
• CAS NO: 20267-87-2
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 371.38384
• EINECS: 243-662-8
• Mol File: 20267-87-2.mol

Chemical Properties

• Melting Point: 135-136 °C(lit.)
• Boiling Point: 507.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.422±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 14.11±0.20(Predicted)
• Merck: 13,2061
• CAS DataBase Reference: CHELIDONINE MONOHYDRATE*(CAS DataBase Reference)
• NIST Chemistry Reference: CHELIDONINE MONOHYDRATE*(20267-87-2)
• EPA Substance Registry System: CHELIDONINE MONOHYDRATE*(20267-87-2)

Safety Data

• Hazardous Substances Data: 20267-87-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Chelidonine monohydrate is used as a therapeutic agent for its potential analgesic and anti-inflammatory properties, offering relief from pain and reducing inflammation in various conditions.
Used in Oncology:
Chelidonine monohydrate is used as an antitumor agent for its ability to inhibit the growth of cancer cells, induce apoptosis, and exhibit synergistic effects when combined with conventional chemotherapeutic drugs, enhancing their efficacy and overcoming drug resistance.
Used in Neurodegenerative Disorders Treatment:
Chelidonine monohydrate is used as a potential treatment for neurodegenerative disorders due to its potential neuroprotective and anti-inflammatory properties, which may help slow down the progression of these diseases.
Used in Autoimmune Diseases Treatment:
Chelidonine monohydrate is used as a potential treatment for autoimmune diseases, leveraging its anti-inflammatory properties to modulate the immune system and alleviate symptoms associated with these conditions.

Upstream product

• 6901-00-4 (+/-)-norchelidonine 
• 33458-78-5 (4bR^*,10bS^*)-5-benzyloxycarbonyl-2,3,7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzophenanthridin-11-one 
• 33458-79-6 (4bR^*,10bS^*,11R^*)-5-benzyloxycarbonyl-2,3,7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzophenanthridin-11-ol 
• 476-32-4 chelidonine 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 33316-44-8 4,5-methylenedioxybenzocyclobutene-1-carboxylic acid 
• 33316-45-9 benzyl N-(4,5-methylenedioxybenzocyclobuten-1-yl)carbamate 
• 29544-25-0 2,3-methylenedioxybenzylaminoacetaldehyde dimethylacetal 
• 33332-08-0 2-bromomethyl-3,4-methylenedioxystyrene 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 943-13-5 5-cyano-5,6-dihydrocyclobuta(f)-1,3-benzodioxole 
• 87091-25-6 (4,5-methylenedioxybenzocyclobuten-1-yl)carbonyl chloride 
• 87091-22-3 N,N-dimethyl-(5,6-methylenedioxy-2-vinyl)benzylamine 
• 86-51-1 2,3-dimethyoxybenzaldehyde 

Relevant articles and documents

A NOVEL AND BIOMIMETIC SYNTHESIS OF (+/-)-CHELAMINE, (+/-)-CHELIDONINE, SANGUINARINE, AND DIHYDROSANGUINARINE FROM COPTISINE VIA A COMMON INTERMEDIATE

(+/-)-Chelamine and (+/-)-chelidonine, B/C cis hexahydrobenzophenanthridine alkaloids were stereoselectively synthesized from coptisine via the key intermediate, which was also converted to fully aromatized benzophenanthridine alkaloids, sanguinarine and dihydrosanguinarine.

Total Synthesis of (+/-)-Chelidonine

Condensation of the Schiff base 8 with 3,4-(methylenedioxy)homophthalic anhydride (13) was exploited as the key step in a total synthesis of the benzophenanthridine alkaloid (+/-)-chelidonine (1).A variety of reaction conditions were investigated in order to maximize the production of the desired thermodynamically less stable cis diastereomer.A method was devised for the conversion of 24 to its acid chloride without production of the indenoisoquinoline 30.The migration of an aromatic ring was observed on treatment of the diazo ketone 26 with acid.This reaction is reminiscent of the Hayashi rearrangement.

A TOTAL SYNTHESIS OF CHELIDONINE

Condensation of homophthalic anhydride 3 with the Schiff base 4 is exploited as the key step in a total synthesis of the benzophenanthridine alkaloid (+/-)-chelidone (8).

Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2+2] cycloaddition cascade

Total syntheses of chelidonine and norchelidonine featuring an enamide-benzyne-[2 + 2] cycloaddition initiated cascade is described. The cascade includes a pericyclic ring-opening and intramolecular Diels-Alder reaction.