Chelidonine supplier | CasNO.476-32-4

Name
CHELIDONINE
EINECS 207-504-1
CAS No. 476-32-4
Article Data4
CAS DataBase
Density 1.422 g/cm³
Solubility
Melting Point 135-140 °C
Formula C₂₀H₁₉NO₅
Boiling Point 507.4 °C at 760 mmHg
Molecular Weight 353.375
Flash Point 260.7 °C
Transport Information UN 2811
Appearance
Safety 20-45-36/37
Risk Codes 25-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms Chelidonine(6CI,7CI,8CI);[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol,5b,6,7,12b,13,14-hexahydro-13-methyl-, [5bR-(5ba,6b,12ba)]-;(+)-Chelidonine;Chelidonin;Stylophorine;[5bR-(5ba,6b,12ba)]-5b,6,7,12b,13,14-Hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol;
PSA 60.39000
LogP 2.26920

Synthetic route

: 1032645-05-8
C27H21NO7

: 476-32-4
chelidonine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In 1,4-dioxane at 20℃; for 19h; Reflux; Inert atmosphere;	88%

: 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

: 476-32-4
chelidonine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; 1,4-dioxane for 17h; Reflux;	82%

: 64-17-5
ethanol

: 24181-71-3
(+)-Didehydrochelidonin

NaBH4: NaBH4

: 476-32-4
chelidonine

...Expand

: 1337985-26-8
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b,11,12-tetrahydrobenzo[c]phenanthridin-6(5H)-one

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 7 h / 85 °C / Inert atmosphere 2.1: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere 3.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 4.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 4.2: 2 h / 0 °C / Inert atmosphere 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 6.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 7.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 8.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 8 steps
1.1: potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 7 h / 85 °C / Inert atmosphere
2.1: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere
3.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C
4.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere
4.2: 2 h / 0 °C / Inert atmosphere
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C
6.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere
7.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr
8.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere
View Scheme

: 1337985-30-4
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b-dihydrobenzo[c]phenanthridin-6(5H)-one

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere 2.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 3.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 3.2: 2 h / 0 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 5.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 6.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 steps
1.1: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere
2.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C
3.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere
3.2: 2 h / 0 °C / Inert atmosphere
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C
5.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere
6.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr
7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere
View Scheme

: 1337985-33-7
(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 2.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 2.2: 2 h / 0 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 5.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 6 steps
1.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C
2.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere
2.2: 2 h / 0 °C / Inert atmosphere
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C
4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere
5.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr
6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere
View Scheme

: C22H19NO6

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C 2: potassium hydroxide / 2 h / 0 - 20 °C 3: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C 5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 6: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 7: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 8: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme

Yield

Multi-step reaction with 8 steps
1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C
2: potassium hydroxide / 2 h / 0 - 20 °C
3: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C
4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C
5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere
6: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C
7: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C
8: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux
View Scheme

: methyl ((1S,2R)-2-(4-(hydroxymethyl)benzo[d][1,3]dioxol-5-yl)-1-(6-vinylbenzo[d][1,3]dioxol-5-yl)but-3-en-1-yl)carbamate

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C 3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 4: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 5: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 6: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C
2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C
3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere
4: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C
5: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C
6: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux
View Scheme

: methyl (6R,7S)-6-vinyl-7-(6-vinylbenzo[d][1,3]dioxol-5-yl)-6,9-dihydro-[1,3]dioxolo[4,5-h]isoquinoline-8(7H)-carboxylate

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 2: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 3: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 4: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme

Yield

Multi-step reaction with 4 steps
1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere
2: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C
3: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C
4: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux
View Scheme

: methyl (5bR,12bS)-5b,14-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine-13(12bH)-carboxylate

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 2: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 3: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme

: methyl (5bR,6S,7S,12bS)-6-bromo-7-hydroxy-5b,7,12b,14-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine-13(6H)-carboxylate

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 2: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme

: C23H22BrNO6

: 476-32-4
chelidonine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 3: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 4: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 5: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme

Yield

Multi-step reaction with 5 steps
1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C
2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere
3: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C
4: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C
5: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux
View Scheme

: 3744-87-4, 7764-95-6, 15761-38-3
N-t-butyloxycarbonyl-DL-alanine

: 476-32-4
chelidonine

: O-(N-tert-butoxycarbonyl-alanyl) chelidonine

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	95.4%

: 118-48-9
isatoic anhydride

: 476-32-4
chelidonine

: C27H24N2O6

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 60℃; for 7h;	95.1%

: 476-32-4
chelidonine

A: 76786-86-2, 98302-76-2, 98302-77-3
(+)-chelidonine N-oxide

B: 76786-86-2, 98302-76-2, 98302-77-3
(+)-chelidonine N-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 0.666667h; Ambient temperature;	A 14.5% B 83%
With 3-chloro-benzenecarboperoxoic acid In chloroform for 1h; Ambient temperature;	A 14.5% B 83%

: 122-01-0
4-chloro-benzoyl chloride

: 476-32-4
chelidonine

: O-(4-chlorobenzoyl) chelidonine

Conditions

Conditions	Yield
With pyridine In dichloromethane	81%

: 543-27-1
isobutyl chloroformate

: 476-32-4
chelidonine

: O-isobutoxycarbonyl chelidonine

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 10h;	78.1%

: 501-53-1
benzyl chloroformate

: 476-32-4
chelidonine

: C28H25NO7

Conditions

Conditions	Yield
With pyridine In chloroform at 20℃;	77.3%

: 98-88-4
benzoyl chloride

: 476-32-4
chelidonine

: C27H23NO6

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	71.1%

: 541-41-3
chloroformic acid ethyl ester

: 476-32-4
chelidonine

: C23H23NO7

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 5h;	70.5%

: 49609-84-9
2-Chloronicotinoyl chloride

: 476-32-4
chelidonine

: O-(2-chloronicotinoyl) chelidonine

Conditions

Conditions	Yield
With pyridine In chloroform	67.2%

: 4635-59-0
4-Chlorobutanoyl chloride

: 476-32-4
chelidonine

: O-(4-chlorobutyryl) chelidonine

Conditions

Conditions	Yield
With pyridine In dichloromethane	58.1%

: 112-67-4
n-hexadecanoyl chloride

: 476-32-4
chelidonine

: O-palmitoyl chelidonine

Conditions

Conditions	Yield
With pyridine In chloroform	50.8%

: 110-53-2
1-Bromopentane

: 476-32-4
chelidonine

: O-(n-pentyl) chelidonine

Conditions

Conditions	Yield
With sodium hydride	50.4%

: 98-59-9
p-toluenesulfonyl chloride

: 476-32-4
chelidonine

: O-(p-toluenesulfonyl) chelidonine

Conditions

Conditions	Yield
With pyridine In chloroform at 20℃; for 10h;	50%

: 1186196-67-7
C18H22N2O9S

: 476-32-4
chelidonine

: 4-((6-((4-(((6S)-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-yl)oxy)-4-oxobutanoyl)oxy)hexyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	47%

: 122-04-3
4-nitro-benzoyl chloride

: 476-32-4
chelidonine

: C27H22N2O8

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃;	46%

: 1186196-66-6
4-(2-(2-((3-carboxypropanoyl)oxy)ethoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide

: 476-32-4
chelidonine

: 4-(2-(2-((4-(((6S)-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-yl)oxy)-4-oxobutanoyl)oxy)ethoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	46%

: 4-(2-(3-carboxypropanamido)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide

: 476-32-4
chelidonine

: 4-(2-(4-(((6S)-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-yl)oxy)-4-oxobutanamido)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	45%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;	45%

: 1393477-78-5
C17H20N2O9S

: 476-32-4
chelidonine

: 4-(4-((5-(((6S)-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-yl)oxy)-5-oxopentanoyl)oxy)butoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	45%

: C17H16N2O9S

: 476-32-4
chelidonine

: 4-((4-((5-(((6S)-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-yl)oxy)-5-oxopentanoyl)oxy)but-2-yn-1-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	44%

: C15H17N3O8S

: 476-32-4
chelidonine

: 4-(2-(5-(((6S)-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-yl)oxy)-5-oxopentanamido)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	43%

: C16H19N3O8S

: 476-32-4
chelidonine

: 4-(3-(5-(((6S)-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-yl)oxy)-5-oxopentanamido)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	41%

: C15H17N3O8S

: 476-32-4
chelidonine

: 4-((1-(4-(((6S)-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-yl)oxy)-4-oxobutanamido)propan-2-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	38%

: 1393477-75-2
4-(4-((3-carboxypropanoyl)oxy)n-propoxy)-3-benzenesulfonyl-1,2,5-oxadiazole-2-oxide

: 476-32-4
chelidonine

: 4-(3-((4-(((6S)-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-yl)oxy)-4-oxobutanoyl)oxy)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	38%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 10h;	38%

: 542-69-8
1-iodo-butane

: 476-32-4
chelidonine

: C24H27NO5

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 10h;	36.5%

: 1393477-77-4
C16H18N2O9S

: 476-32-4
chelidonine

: 4-(3-((5-(((6S)-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-yl)oxy)-5-oxopentanoyl)oxy)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	36%

: C19H24N2O9S

: 476-32-4
chelidonine

: 4-((6-((5-(((6S)-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-yl)oxy)-5-oxopentanoyl)oxy)hexyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	35%

: 4-(3-(3-carboxypropanamido)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide

: 476-32-4
chelidonine

: 4-(3-(4-(((6S)-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-yl)oxy)-4-oxobutanamido)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	34%

: C17H20N2O10S

: 476-32-4
chelidonine

: 4-(2-(2-((5-(((6S)-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-yl)oxy)-5-oxopentanoyl)oxy)ethoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	33%

Chelidonine Specification

Chelidonine is an organic compound with the formula C₂₀H₁₉NO₅, and its systematic name is the same with the product name. With the CAS registry number 476-32-4, it is also named as (5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol. It belongs to the product categories of Alkaloids. Its EINECS number is 207-504-1. In addition, the molecular weight is 353.37. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Natural Product.

Physical properties of Chelidonine are: (1)ACD/LogP: 2.899; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.91; (4)ACD/LogD (pH 7.4): 2.85; (5)ACD/BCF (pH 5.5): 9.53; (6)ACD/BCF (pH 7.4): 84.51; (7)ACD/KOC (pH 5.5): 91.21; (8)ACD/KOC (pH 7.4): 808.63; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 60.39 Å²; (13)Index of Refraction: 1.667; (14)Molar Refractivity: 92.483 cm³; (15)Molar Volume: 248.441 cm³; (16)Polarizability: 36.663×10^-24cm³; (17)Surface Tension: 58.78 dyne/cm; (18)Density: 1.422 g/cm³; (19)Flash Point: 260.66 °C; (20)Enthalpy of Vaporization: 81.866 kJ/mol; (21)Boiling Point: 507.389 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of Chelidonine: it can be used to produce O-ethoxycarbonyl chelidonine at the temperature of 20 °C. It will need reagent pyridine and solvent CH₂Cl₂ with the reaction time of 5 hours. The yield is about 70.5%.

Chelidonine can be used to produce O-ethoxycarbonyl chelidonine at the temperature of 20 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic if swallowed. It is harmful by inhalation, in contact with skin and if swallowed. When using it, you should not eat or drink. Moreover, you need to wear suitable protective clothing and gloves. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O1c2c(OC1)c3c(cc2)[C@@H]5[C@H](N(C3)C)c4cc6OCOc6cc4C[C@@H]5O
(2)Std. 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
(3)Std. InChIKey: GHKISGDRQRSCII-ZOCIIQOWSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
cat	LD50	subcutaneous	140mg/kg (140mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
dog	LD50	subcutaneous	500mg/kg (500mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
frog	LD50	subcutaneous	160mg/kg (160mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
mouse	LD50	intravenous	35mg/kg (35mg/kg)	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 5, Pg. 163, 1946.
mouse	LD50	subcutaneous	125mg/kg (125mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.
mouse	LD50	unreported	2750mg/kg (2750mg/kg)	Herba Polonica. Vol. 25, Pg. 209, 1979.
rabbit	LD50	subcutaneous	360mg/kg (360mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

Product Name

CHELIDONINE

Synthetic route

Chelidonine Specification

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