(R)-2-(6-Methoxynaphthalen-2-yl)propanoic acid

Names

[ Name ]:
(R)-2-(6-Methoxynaphthalen-2-yl)propanoic acid

[Synonym ]:
piproxen
2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (αR)-
(+)-(S)-Naproxen
Anaprox
(R)-Naproxen
2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (αS)-
MFCD00870716
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
(2R)-2-(6-Methoxy-2-naphthyl)propanoic acid
NAPRELAN
(2S)-2-(6-Methoxy-2-naphthyl)propanoic acid
2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (S)-
(2S)-2-(6-Methoxynaphth-2-yl)propanoic acid
2-naphthaleneacetic acid, 6-methoxy-a-methyl-, (aS)-
Naproxen
Apronax
EINECS 245-966-6
(+)-NAPROXEN
(S)-(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid
(S)-(+)-Naproxen
ALEVE
(S)-naproxen
Naprosyn

Biological Activity

[Description]:

l-Naproxen ((R)-Naproxen) is an enantiomer of (S)-Naproxen. l-Naproxen can inhibit Cdc42 and Rac1 (EC50=96 μM and 212 μM, respectively), and show anti-tumor activity[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

l-Naproxen (30-1000 μM; 2 h) inhibits Rac1 and Cdc42 activity selectively in cells[3]. l-Naproxen (0-300 μM; 48 h) inhibits migration of immortalized human ovarian cancer cells[3]. l-Naproxen (300 μM; 48 h) shows activity via a COX-independent mechanism[3]. Cell Viability Assay[3] Cell Line: HeLa cells Concentration: 30-1000 μM Incubation Time: 2 hour Result: Inhibited Rac1 and Cdc42 activity in a dose dependent manner with the EC50 values of 212 μM and 96 μM, respectively. Cell Migration Assay [3] Cell Line: OvCa429 and OvCa433 cells Concentration: 0-300 μM Incubation Time: 48 hour Result: Had a statistically significant inhibitory effect at 300 μM compared to untreated controls. Western Blot Analysis[3] Cell Line: OvCa433 cells Concentration: 300 μM Incubation Time: 48 hour Result: Exhibited higher levels of phosphorylated EGFR (pEGFR) and (pERK) compared to unstimulated controls.

[References]

[1]. Sonika Batra, et al. Enantiomeric Resolution of (RS)-Naproxen and Application of (S)- Naproxen in the Direct and Indirect Enantioseparation of Racemic Compounds by Liquid Chromatography: A Review. Curr Med Chem. 2017;24(8):758-780.

[2]. M Iwaki, et al. Stereoselective disposition of naproxen glucuronide in the rat. Drug Metab Dispos. 1995 Oct;23(10):1099-103.

[3]. Tudor I Oprea, et al. Novel Activities of Select NSAID R-Enantiomers against Rac1 and Cdc42 GTPases. PLoS One. 2015 Nov 11;10(11):e0142182.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
403.9±20.0 °C at 760 mmHg

[ Melting Point ]:
156-158ºC(lit.)

[ Molecular Formula ]:
C₁₄H₁₄O₃

[ Molecular Weight ]:
230.259

[ Flash Point ]:
154.5±15.3 °C

[ Exact Mass ]:
230.094299

[ PSA ]:
46.53000

[ LogP ]:
3.00

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.609

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36/S37

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3.0

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%