Fexaramine

Base Information

• Chemical Name: Fexaramine
• CAS No.: 574013-66-4
• Molecular Formula: C₃₂H₃₆N₂O₃
• Molecular Weight: 496.649
• UNII: WTG9GFA65U
• DSSTox Substance ID: DTXSID80870369
• Nikkaji Number: J1.893.517A,J2.795.664E
• Wikipedia: Fexaramine
• Wikidata: Q19597241
• Pharos Ligand ID: NBZKKJ9SVRK5
• Metabolomics Workbench ID: 147123
• ChEMBL ID: CHEMBL192966
• Mol file: 574013-66-4.mol

Synonyms:fexaramine

Chemical Property of Fexaramine

Chemical Property:

• Boiling Point: 677.7±55.0 °C(Predicted)
• PKA: 4.95±0.24(Predicted)
• Flash Point: 363.7oC
• PSA: 49.85000
• Density: 1.158±0.06 g/cm3(Predicted)
• LogP: 6.71930
• Storage Temp.: Desiccate at +4°C
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 496.27259301
• Heavy Atom Count: 37
• Complexity: 743

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fexaramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)C2=CC=C(C=C2)CN(C3=CC=CC(=C3)C=CC(=O)OC)C(=O)C4CCCCC4
• Isomeric SMILES: CN(C)C1=CC=C(C=C1)C2=CC=C(C=C2)CN(C3=CC=CC(=C3)/C=C/C(=O)OC)C(=O)C4CCCCC4
• Description: The farnesoid X receptor (FXR) is a nuclear receptor that acts as a bile acid sensor, protecting cells and organs against bile acid toxicity and coordinating cholesterol metabolism, lipid homeostasis, and absorption of dietary fats and vitamins. Fexaramine is an FXR agonist (EC50 = 25 nM) that demonstrates 100-fold increased affinity to FXR compared to endogenous bile acids and 3-fold increased potency compared to the high affinity FXR agonist GW 4064 (; EC50 = 80 nM). Fexaramine does not display activity at the following nuclear receptors: hRXRα, hPPARαγδ, mPXR, hPXR, hLXRα, hTRβ, hRARβ, mCAR, mERRγ, or hVDR.
• Uses: Fexaramine has been used to study its action on RANKL (receptor activator of nuclear factor-κB ligand)-induced osteoclastogenesis in mouse model.

Technology Process of Fexaramine

There total 2 articles about Fexaramine 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:

methanol (67-56-1) + 4-(dimethylamino)benzene-boronic acid (28611-39-4) + 4-bromo-benzaldehyde (1122-91-4) + cyclohexanylcarbonyl chloride (2719-27-9) + 3-(3-tert-butoxycarbonylamino-phenyl)-acrylic acid (1041867-60-0) → (E)-methyl 3-(3-(N-((4’-(dimethylamino)-[1,1‘-biphenyl]-4-yl)methyl)cyclohexanecarboxamido)phenyl)acrylate (574013-66-4)

Guidance literature:

Multistep reaction.;

DOI:10.1039/b300525a

Reference yield:

→ (E)-methyl 3-(3-(N-((4’-(dimethylamino)-[1,1‘-biphenyl]-4-yl)methyl)cyclohexanecarboxamido)phenyl)acrylate (574013-66-4)

Guidance literature:

Reference yield:

(E)-methyl 3-(3-(N-((4’-(dimethylamino)-[1,1‘-biphenyl]-4-yl)methyl)cyclohexanecarboxamido)phenyl)acrylate (574013-66-4) → (E)-N-((4’-(dimethylamino)-[1,1‘-biphenyl]-4-yl)methyl)-N-(3-(3-(methylamino)-3-oxoprop-1-en-1-yl)phenyl)cyclohexanecarboxamide

Guidance literature:

Multi-step reaction with 2 steps

1.1: water; sodium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C

2.2: 0.5 h

With water; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

upstream raw materials:

methanol

4-(dimethylamino)benzene-boronic acid

4-bromo-benzaldehyde

cyclohexanylcarbonyl chloride

Refernces

• 1、 Nicolaou,Evans, Ronald M,Roecker,Hughes, Robert,Downes, Michael,Pfefferkorn, Jeffery A. "Discovery and optimization of non-steroidal FXR agonists from natural product-like libraries.". . p. 908 - 920. Retrieved 2007/10/03.