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ChemicalBook--->CAS DataBase List--->436-77-1

436-77-1

436-77-1 Structure

436-77-1 Structure
IdentificationBack Directory
[Name]

(+)-FANGCHINOLINE
[CAS]

436-77-1
[Synonyms]

(+)-limacine
Tetrandrine B
Hanfangichin B
FANGCHINO-LINE
(+)-FANGCHINOLINE
FANGCHINOLINE (RG)
7-o-demethyltetrandrine
12-O-MethylatherosperMoline
Hanfangchin B(Fangchinoline)
Fangchinoline, Demethyltetrandrine
6,6',12-TRIMETHOXY-2,2'-DIMETHYLBERBAMAN-7-OL
(1S)-6,6',12-Trimethoxy-2,2'-dimethylberbaman-7-ol
2’-dimethyl-6,6’,12-trimethoxy-(1-beta)-berbaman-7-o
(1-beta)-2,2’-dimethyl-6,6’,12-trimethoxyberbaman-7-ol
Berbaman-7-ol,6,6',12-trimethoxy-2,2'-dimethyl-, (1β)-
(1S)-7-Hydroxy-6,6',12-trimethoxy-2,2'-dimethylberbaman
[Molecular Formula]

C37H40N2O6
[MDL Number]

MFCD00221726
[MOL File]

436-77-1.mol
[Molecular Weight]

608.72
Chemical PropertiesBack Directory
[Melting point ]

240~242℃
[Boiling point ]

709.7±60.0 °C(Predicted)
[density ]

1.204±0.06 g/cm3(Predicted)
[storage temp. ]

4°C, protect from light
[solubility ]

Soluble in chloroform and methanol;
[form ]

powder to crystal
[pka]

9.38±0.20(Predicted)
[color ]

White to Orange to Green
[Water Solubility ]

slightly soluble in water
Safety DataBack Directory
[HS Code ]

2939.79.0000
Hazard InformationBack Directory
[Description]

A bisbenzylisoquino!ine alkaloid obtained from Limacia cuspidata (Miers.) Hook. f. et Thorn., the base crystallizes from Me2CO in the form of long, colourless needles. It is strongly laevorotatory with [α]D - 2120 (CHCI3) and has been shown to be the optical antipode of fanchinoline (q.v.).
[Description]

Fangchinoline is an alkaloid that has been found in S. tetrandrae and has diverse biological activities, including anti-inflammatory, neuroprotective, and anticancer properties. It inhibits the activity of sheep COX and decreases IL-6-induced proliferation of MH60 mouse hybridoma cells with IC50 values of 129 and 3.7 μM, respectively. Fangchinoline (1 and 10 μM) reduces cyanide-induced increases in secreted glutamate levels and cell death in primary neonatal rat cerebellar granule neurons. It decreases proliferation of PC3 human prostate cancer cells by 63 and 86% when used at concentrations of 20 and 30 μM, respectively. Fangchinoline reduces tumor growth in a PC3 mouse xenograft model when administered at a dose of 5 mg/kg per day for 12 days.
[Uses]

(+)-Fangchinoline is an isolate from Stephania Tetrandra that shows anti-cancer activity. It inhibits breast adenocarcinoma proliferation through apoptosis induction. In addition, it has been shown to inhibit HIV-Type 1 replication.
[Definition]

ChEBI: A bisbenzylisoquinoline alkaloid that is (1beta)- berbaman which has been substituted by methyl groups at the 2 and 2' positions, by methoxy groups at the 6, 6', and 12 positions, and by a hydroxy group at position 7. Isolated from S ephania tetrandra, it has been found to possess neuroprotective and anti-tumour activity.
[References]

Tomita, Furukawa., Tetrahedron Lett., 4293 (1966)
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