4-PHENOXYBENZYLAMINE Chemical Properties

Boiling point:

138°C 5mm

Density 

1,12 g/cm³

refractive index 

1.59

Flash point:

150℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in DMSO

form 

clear liquid

pka

9.13±0.10(Predicted)

color 

Colorless to Light orange to Yellow

InChI

InChI=1S/C13H13NO/c14-10-11-6-8-13(9-7-11)15-12-4-2-1-3-5-12/h1-9H,10,14H2

InChIKey

CCAZAGUSBMVSAR-UHFFFAOYSA-N

SMILES

C1(CN)=CC=C(OC2=CC=CC=C2)C=C1

CAS DataBase Reference

107622-80-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi,N,T

Risk Statements 

36/37/38-50-41-37/38-25

Safety Statements 

26-36/37/39-61-45-39

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

2922290090

4-PHENOXYBENZYLAMINE Usage And Synthesis

Uses

4-Phenoxybenzylamine inhibits the function of the NS3 protein by stabilizing an inactive conformation with an IC50 of about 500 μM against FL NS3/4a.

Biological Activity

4-Phenoxybenzylamine inhibits the function of NS3 protein by stabilizing the inactive conformation, and inhibits FL NS3/4a with an IC50 value of approximately 500 μM.

Synthesis

The general procedure for the synthesis of 4-phenoxybenzylamine from 4-phenoxybenzonitrile was as follows: 4-phenoxybenzonitrile (200 mg, 1.00 mmol) was dissolved in 8 mL of methanol, and 5% Pd/C catalyst (0.2 equiv, 400 mg) was added. The reaction was stirred under hydrogen atmosphere for 3 h. The reaction was filtered through diatomaceous earth after completion. The filtrate was purified by preparative thin layer chromatography (pTLC) to afford 4-phenoxybenzylamine as a white solid (179 mg, 88% yield) using a dichloromethane solution containing 10% methanol and 2% triethylamine as an unfolding agent. Subsequently, compound 42 (1.1 eq., 22 mg) was dissolved in toluene and 2,5-dimethoxyaniline (1 eq., 8 mg), BINAP (0.3 eq., 11 mg), Pd(OAc)2 (0.15 eq., 2 mg), and Cs2CO3 (2.5 eq., 46 mg) were added and the mixture was stirred and reacted for 15 hr at 105 °C. At the end of the reaction, the solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography using ethyl acetate as eluent. Finally, the compound was further purified by preparative thin layer chromatography (pTLC) using hexane solution containing 50% ethyl acetate as the unfolding agent to afford compound 34 as a colorless oil (12.4 mg, 48% yield).

in vitro

target

References

[1] Saalau-Bethell SM, et al. Discovery of an allosteric mechanism for the regulation of HCV NS3 protein function. Nat Chem Biol. 2012 Nov;8(11):920-5. DOI:10.1038/nchembio.1081

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