Chelidonine

Base Information

• Chemical Name: Chelidonine
• CAS No.: 476-32-4
• Molecular Formula: C20H19NO5
• Molecular Weight: 353.375
• Hs Code.: 2933990090
• European Community (EC) Number: 207-504-1
• UNII: 8K7EK8446J,4UDG3LY0GT
• DSSTox Substance ID: DTXSID10878474
• Nikkaji Number: J5.974I
• Wikipedia: Chelidonine
• Wikidata: Q1069066
• Metabolomics Workbench ID: 54393
• ChEMBL ID: CHEMBL496867
• Mol file: 476-32-4.mol

Synonyms:chelidonine;chelidonine bisulfate;chelidonine hydrochloride;chelidonine sulfate;chelidonine tartrate

Chemical Property of Chelidonine

Chemical Property:

• Vapor Pressure: 4.06E-11mmHg at 25°C
• Melting Point: 135-140 °C
• Refractive Index: 1.667
• Boiling Point: 507.4 °C at 760 mmHg
• PKA: 14.11±0.20(Predicted)
• Flash Point: 260.7 °C
• PSA: 60.39000
• Density: 1.422 g/cm³
• LogP: 2.26920
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 353.12632271
• Heavy Atom Count: 26
• Complexity: 560

Purity/Quality:

99% ^*data from raw suppliers

Chelidonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 25-20/21/22
• Safety Statements: 20-45-36/37

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CC2=C(C=CC3=C2OCO3)C4C1C5=CC6=C(C=C5CC4O)OCO6
• Isomeric SMILES: CN1CC2=C(C=CC3=C2OCO3)[C@@H]4[C@H]1C5=CC6=C(C=C5C[C@@H]4O)OCO6
• Description: Chelidonine, also named ranunculine, is a benzophenanthridine alkaloid isolated from the whole plant of Chelidonium majus. L. It has been used as a painkiller in clinical treatment based on its morphine-like analgesic effect. Pharmacological researches in recent years have demonstrated that chelidonine played a role in antitumor, antibacterial, spasmolysis activities, and so on. And the antitumor activity is drawing more and more attention. However, its mechanisms of function remain unclear, which needs to be clarified in the future. Chelidonine is an alkaloid fundamental parent, a benzophenanthridine alkaloid and an alkaloid antibiotic. Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity . Chelidonine is a benzophenanthridine alkaloid that has been isolated from C. majus. It induces Bcl-2- and caspase-dependent apoptosis in HepG2 human liver carcinoma cells with an LC50 value of 12 μM and in Jurkat human T cells when used at a concentration of 1 μM. Chelidonine also downregulates hTERT expression in HepG2 cells, reduces telomerase activity, and induces cell senescence. Chelidonine, also named ranunculine, is a kind of alkaloid isolated from the whole plant of Chelidonium majus. L . As a kind of traditional Chinese medicine, Chelidonium majus. L was firstly recorded in Chiu Huang Pen Ts’ao of Ming dynasty. In the seventeenth century, it has been used for the treatment of jaundice, biliary colic, and cholelithiasis. In 1941, a researcher from Soviet Union reported that it showed good effect for the treatment of cutaneous tuberculosis. This plant has multiple effects on different diseases, including anti-inflammatory, analgesia, relieving cough, inducing diuresis, anticancer, antifungal, relieving asthma, and detoxification. It was recorded in the Pharmacopoeia of the People’s Republic of China (1977) .The material basis for Chelidonium majus. L is alkaloid. Among which, chelidonine, a benzophenanthridine alkaloid, is the main effective ingredient . Although great progresses have been made in the chemical synthesis of chelidonine recently, the biosynthetic pathways of chelidonine remain unclear, which still need in-depth study and exploration in the future
• Uses: Chelidonine is the major alkaloid component of Chelidonium majus. Chelidonium majus L. is the only species of the tribe Chelidonieae of the Papaveraceae family. The Papaveraceae family is rich in specific alkaloids. C. majus contains various isoquinoline alkaloids with protopine, protoberberine and benzophenanthridine structures. This benzophenanthridine alkaloid can induce apoptosis in some transformed or malignant cell lines. D-Chelidonine, the main alkaloid of Chelidonium majus, was first isolated in 1839.? Chelidonine is a major bioactive, isoquinoline alkaloid ingredient in Chelidonium majus. Benzylisoquinoline alkaloids (BIAs) are a structurally diverse group of plant specialized metabolites with a long history of investigation. A restricted number of enzyme families have been implicated in BIA metabolism. Whereas some enzymes exhibit a relatively broad substrate range, others are highly substrate specific. A small number of plant species, including opium poppy (Papaver somniferum) and other members of the Ranunculales, have emerged as model systems to study BIA metabolism. Recently, the emergence of transcriptomics, proteomics and metabolomics has expedited the discovery of new BIA biosynthetic genes. Poison; central nervous system depres- sant causing sleepiness, depression, slowing of the pulse, coma and circulatory failure.
• Physical properties: Appearance: white crystal or crystalline powder, monoclinic prism crystal. Solubility: insoluble in water; soluble in ethanol, chloroform, and amyl alcohol. Melting point: 135–136 °C. Boiling point: 220 °C. Specific optical rotation: +115°.
• Clinical Use: Chelidonine has been used as a painkiller in clinical application due to its significant analgesic effect. Chelidonine phosphate can be used for treatment of gastrointestinal and ulcer pain, as a substitute of morphine preparations. Wei Tong Shu capsule is used to treat pain caused by gastric convulsion, chronic gastritis, gastric ulcer, and duodenal ulcer. Its main effective compositions are chelidonine and protopine. Fu Fang Zhong Yao Tong An injection has collateral dredging and analgesic effects and can be used for the treatment of moderate pain caused by chemoradiotherapy or non-chemoradiotherapy of gastric cancer, lung cancer, and liver cancer. Its two main components are chelidonine and sinomenine. Ukrain (NSC-631570), a phosphorothioate derivative of chelidonine, has been used in clinical treatment as an effective antitumor drug for the treatment of lung cancer, breast cancer, prostate cancer, and pancreatic cancer.

Technology Process of Chelidonine

There total 21 articles about Chelidonine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

C27H21NO7 (1032645-05-8) → chelidonine (476-32-4)

Guidance literature:

With lithium aluminium tetrahydride; In 1,4-dioxane; at 20 ℃; for 19h; Reflux; Inert atmosphere;

DOI:10.1002/chem.200701775

Reference yield: 82.0%

methyl (5bR,5cR,6aS,11bS)-5b,6a,11b,13-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]oxireno[2,3-a]phenanthridine-12(5cH)-carboxylate → chelidonine (476-32-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; 1,4-dioxane; for 17h; Reflux;

DOI:10.1002/anie.202005151

Reference yield:

(+)-11,12-isopropylidenedioxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridine (1337985-43-9) → chelidonine (476-32-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 50 ℃; for 22h; Inert atmosphere;

DOI:10.1016/j.tet.2011.07.091

upstream raw materials:

ethanol

(+)-Didehydrochelidonin

C₂₇H₂₁NO₇

(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b,11,12-tetrahydrobenzo[c]phenanthridin-6(5H)-one

Downstream raw materials:

(+/-)-chelidonine

Refernces

• 1、 Fyfe, James W. B.,Hutchings-Goetz, Luke S.,Snaddon, Thomas N.,Yang, Chao. "Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis". . p. 17556 - 17564. Retrieved 2020/08/14.
• 2、 Fleming, Matthew J.,McManus, Helen A.,Rudolph, Alena,Chan, Walter H.,Ruiz, Jeremy,Dockendorff, Chris,Lautens, Mark. "Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a PdII-catalyzed ring-opening strategy". experimental part. p. 2112 - 2124. Retrieved 2009/04/06.