Fangchinoline

Base Information

• Chemical Name: Fangchinoline
• CAS No.: 436-77-1
• Molecular Formula: C₃₇H₄₀N₂O₆
• Molecular Weight: 608.734
• NSC Number: 77036
• UNII: 953592C3ZB
• DSSTox Substance ID: DTXSID40893498
• Nikkaji Number: J11.388C
• Wikipedia: Fangchinoline
• Wikidata: Q15410976
• Metabolomics Workbench ID: 140034
• ChEMBL ID: CHEMBL504256
• Mol file: 436-77-1.mol

Synonyms:(1beta)-isomer of fangchinoline;7-O-demethyl-tetrandrine;7-O-demethyltetrandrine;berbaman-7-ol, 6,6',12-trimethoxy-2,2'-dimethyl-, (1beta)-;fangchinoline;isofangchinoline;limacine;thaligine;thalrugosine

Chemical Property of Fangchinoline

Chemical Property:

• Vapor Pressure: 8.25E-21mmHg at 25°C
• Melting Point: 240～242℃
• Refractive Index: 1.601
• Boiling Point: 709.7 °C at 760 mmHg
• PKA: 9.38±0.20(Predicted)
• Flash Point: 383 °C
• PSA: 72.86000
• Density: 1.204 g/cm³
• LogP: 6.73520
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 608.28863700
• Heavy Atom Count: 45
• Complexity: 963

Purity/Quality:

more than 98% ^*data from raw suppliers

(+)-Fangchinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)O)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@H]6C7=C(O3)C(=C(C=C7CCN6C)OC)O)OC)OC
• 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.). 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.

Technology Process of Fangchinoline

There total 8 articles about Fangchinoline 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: 51.5%

Tetrandrin (518-34-3,5990-67-0) → fangchinoline (436-77-1,10172-02-8,33889-68-8,38769-07-2,53834-87-0,119478-08-9)

Guidance literature:

With hydrogen bromide; acetic acid; at 90 ℃; for 8h;

DOI:10.1016/j.bioorg.2021.104694

Reference yield: 35.0%

Tetrandrin (518-34-3,5990-67-0) → Atherospermoline (21008-67-3) + (+)-penduline (26137-45-1) + 6',7-Bis-(O-demethyl)-tetrandrine (83087-72-3) + fangchinoline (436-77-1,10172-02-8,33889-68-8,38769-07-2,53834-87-0,119478-08-9)

Guidance literature:

With hydrogen bromide; at 20 ℃; for 24h; Yield given. Further byproducts given;

DOI:10.1002/ardp.19823150705

Reference yield: 35.0%

Tetrandrin (518-34-3,5990-67-0) → Tetrakis-(O-demethyl)-tetrandrin (83113-25-1) + Atherospermoline (21008-67-3) + (+)-penduline (26137-45-1) + 6',7,12-Tris-(O-demethyl)-tetrandrine (83113-24-0) + 6',7-Bis-(O-demethyl)-tetrandrine (83087-72-3) + fangchinoline (436-77-1,10172-02-8,33889-68-8,38769-07-2,53834-87-0,119478-08-9)

Guidance literature:

With hydrogen bromide; at 20 ℃; for 24h; Product distribution; different concentration of HBr, different times and temperatures;

DOI:10.1002/ardp.19823150705

upstream raw materials:

Tetrandrin

(+)-isotetrandrine

Downstream raw materials:

(+)-isotetrandrine

7-isopropoxy fangchinoline

Hernandezine

Refernces

• 1、 Li, Jiayuan,Li, Li,Li, Xuyu,Liu, Yanfei,Shi, Guoru,Wang, Renzhong,Yu, Dequan,Yuan, Jiqiao,Zhou, Jie. "Bioactive bisbenzylisoquinoline alkaloids from the roots of Stephania tetrandra". . . Retrieved 2020/03/17.
• 2、 Pachaly,Praest. "Phenolic derivatives from the bisbenzylisoquinoline alkaloid tetrandrine by selective ether cleavage". . p. 589 - 597. Retrieved 2007/10/02.