944261-79-4

Basic information

• Product Name: 5-(4-Chlorophenyl)-furan-2-carboxylic acid 3,5-dimethoxyphenylamide
• Synonyms: 5-(4-Chlorophenyl)-furan-2-carboxylic acid 3,5-dimethoxyphenylamide;A 803467;5-(4-Chlorophenyl)-N-(3,5-dimethoxyphenyl)-2-furancarboxamide;5-(4-Chlorophenyl)-N-(3,5-dimethoxyphenyl)-;5-4(-Chlorophenyl)-N-(3,5-diMethoxyphenyl)furan-2-carboxaMide;2-FurancarboxaMide,5-(4-chlorophenyl)-N-(3,5-diMethoxyphenyl)-;5-(4-Chlorophenyl)-furan-2-carboxylic acid 3,5;A-803467, >=99%
• CAS NO: 944261-79-4
• Molecular Formula: C₁₉H₁₆ClNO₄
• Molecular Weight: 357.791
• Product Categories: Sodium channel;Ion Channels;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 944261-79-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 128-130?C
• Boiling Point: 450.6 °C at 760 mmHg
• Flash Point: 226.3 °C
• Appearance: white to tan/
• Density: 1.294 g/cm³
• Vapor Pressure: 2.6E-08mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: Store at +4°C
• Solubility: DMSO: >10mg/mL
• PKA: 11.72±0.70(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: 5-(4-Chlorophenyl)-furan-2-carboxylic acid 3,5-dimethoxyphenylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-Chlorophenyl)-furan-2-carboxylic acid 3,5-dimethoxyphenylamide(944261-79-4)
• EPA Substance Registry System: 5-(4-Chlorophenyl)-furan-2-carboxylic acid 3,5-dimethoxyphenylamide(944261-79-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 944261-79-4(Hazardous Substances Data)

Usage

Description

5-(4-Chlorophenyl)-furan-2-carboxylic acid 3,5-dimethoxyphenylamide is a sodium channel blocker with high affinity and selectivity for inhibiting human Nav1.8 sodium channels. It is effective in reducing behavioral responses in various neuropathic and inflammatory pain models.
Used in Pharmaceutical Industry:
5-(4-Chlorophenyl)-furan-2-carboxylic acid 3,5-dimethoxyphenylamide is used as an analgesic for reducing behavioral measures of chronic pain. Its high selectivity and affinity for Nav1.8 sodium channels make it a promising candidate for the development of novel pain therapeutics.

Biological Activity

Selective blocker of Na V 1.8 channels (IC 50 values are 8, 2450, 6740, 7340 and 7380 nM for hNa V 1.8, hNa V 1.3, hNa V 1.7, hNa V 1.5 and hNa V 1.2 channels respectively). Shows no significant activity against TRPV1, P2X 2/3 , Ca V 2.2 and KCNQ2/3 channels. Antinociceptive; potently attenuates mechanical allodynia in two models of neuropathic pain following i.p. administration.

Biochem/physiol Actions

A-803467 blocks Nav1.8 in both half-maximal inactive and resting states with an IC50 of 8 nM and IC50 of 79 nM, respectively. A-803467 is over 100-fold more selective vs. human Nav1.2, 1.3, 1.5 and 1.7.

References

1) Jarvis et al. (2007), A-803467, a potent and selective Nav1.8 sodium channel blocker, attenuates neuropathic and inflammatory pain in the rat; Proc. Natl. Acad. Sci. USA, 104 8520 2) McGaraughty et al. (2008), A selective Nav1.8 sodium channel blocker, A-803467 [5-(4-chlorophenyl-N-(3,5-dimethoxyphenyl)furan-2-carboxamide], attenuates spinal neuronal activity in neuropathic rats; J. Pharmacol. Exp. Ther., 324 1204

InChI:InChI=1/C19H16ClNO4/c1-23-15-9-14(10-16(11-15)24-2)21-19(22)18-8-7-17(25-18)12-3-5-13(20)6-4-12/h3-11H,1-2H3,(H,21,22)

Upstream product

• 585-70-6 5-bromo-furan-2-carboxylic acid 
• 57753-81-8 5-(4-chlorophenyl)furan-2-carboxamide 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 57753-80-7 5-(4-chloro-phenyl)-furan-2-carbonyl chloride 
• 10272-07-8 3.5-dimethoxyaniline 

Relevant articles and documents

T-BuXPhos: A highly efficient ligand for Buchwald-Hartwig coupling in water

An efficient and versatile 'green' catalytic system for the Buchwald-Hartwig cross-coupling reaction in water is reported. In an aqueous micellar medium, the combination of t-BuXPhos with [(cinnamyl)PdCl]2 showed excellent performance for coupling arylbromides or chlorides with a large set of amines, amides, ureas and carbamates. The method is functional-group tolerant, proceeds smoothly (30 to 50 °C) and provides rapid access to the target compounds in good to excellent isolated yields. When applied to the synthesis of a known NaV1.8 modulator, this method led to a significant improvement of the E-factor in comparison with classical organic synthesis. the Partner Organisations 2014.