Chelidonine

Chelidonine

Names
IUPAC name (5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol
Identifiers
CAS Number	476-32-4
3D model (JSmol)	Interactive image
ChemSpider	171216
ECHA InfoCard	100.006.823
PubChem CID	197810
InChI InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1 Key: GHKISGDRQRSCII-ZOCIIQOWSA-N InChI=1/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1 Key: GHKISGDRQRSCII-ZOCIIQOWBJ
SMILES CN1CC2=C(C=CC3=C2OCO3)[C@@H]4[C@H]1C5=CC6=C(C=C5C[C@@H]4O)OCO6
Properties
Chemical formula	C20H19NO5
Molar mass	353.37 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

( Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.

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. The supposed healing properties of greater celandine (Chelidonium majus) were believed in throughout Europe and Asia during the Emperial Roman period (Pliny 1966), and New World aboriginal cultures used BIA-containing plants by using sap or root extracts to treat minor cuts and infections.

The amide was heated in boiling bromobenzene to form the transfused compound. By contrast, thermolysis of the more flexible urethane afforded the desired cis fused product. The building blocks required for the synthesis of chelidonine are urathane and benzyl bromide. The urathane was obtained by first using nitrile, duo to hydrolysis carboxylic acid was generated. The carboxylic acid which on Curtius degradation yielded crude isocyanate (N=C=O). The reaction of crude isocyanate with benzyl alcohol made the urethane, with the NHCOOC7H7 side group. The benzyl bromide was obtained by the conversion of 2,3-methylenedioxybenzaldehyde to 1,2,3,4 - tetrahydro-7,8-methylenedioxyisoquinol by the successive Hofmann and von Braun degradations.

Condensation of urethane and benzyl bromide led to the formation of the oily styrene. From this structure the liquid acetylene was formed. Next, the crystalline tetrahydrobenz[c]phenanthridine was formed. hydroboration and oxidation produced an alcohol. Jones oxidation gave rise to the ketone. And by processing the ketone the desired cis,cis-alcohol was formed. After hydrogenolysis of the benzyloxycarbonyl group, dl-norchelidonine was synthesized.