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

Nav1.8 is a tetrodotoxin-resistant (TTX-R) sodium channel with high activation threshold and slow inactivating kinetics that is highly expressed in small-diameter sensory neurons and has been implicated in signaling various types of pain. A-803467 is a sodium channel blocker with high-affinity and selectivity for inhibiting human Nav1.8 sodium channels (IC50 = 8 nM when stimulated at half-maximal inactivation and IC50 = 79 nM at a resting state). This compound is unusual in that it blocks hNav1.8 at negative resting membrane potentials (many small molecule sodium channel blockers show a reduced affinity for the resting state) and does not demonstrate significant frequency-dependent block during a 10 Hz pulse train. A-803467 dose-dependently reduces behavioral responses in a variety of neuropathic and inflammatory pain models.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 944261-79-4 differently. You can refer to the following data:
1. A selective NaV1.8 sodium channel blocker, reduces behavioral measures of chronic pain.
2. A selective NaV1.8 sodium channel blocker, reduces behavioral measures of chronic pain. Analgesic.

General Description

The small molecule A-803467 is a potent and selective Nav1.8 sodium channel blocker. Nav1.8 is a tetrodotoxin-resistant (TTX-R) sodium channel that contributes to pain sensation by transmitting pain stimuli in peripheral sensory neurons; blockage of this channel by A-803467 reduces pain with varying effectiveness in a number of different models. A-803467 has been used to further understand the role of Nav1.8 in transmitting pain stimuli and also can be used as an analgesic.

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

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

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.