7-Methoxy-1-tetralone

Names

[ Name ]:
7-Methoxy-1-tetralone

[Synonym ]:
EINECS 229-916-0
3,4-dihydro-7-methoxynaphthalen-1(2H)-one
7-Methoxy-3,4-dihydronaphthalen-1(2H)-one
1(2H)-Naphthalenone, 3,4-dihydro-7-methoxy-
MFCD00001696
7-Methoxy-3,4-dihydro-1(2H)-naphthalenone
7-methoxy-3,4-dihydro-2H-naphthalen-1-one

Biological Activity

[Description]:

7-Methoxy-1-tetralone is a potent antitumor agent. 7-Methoxy-1-tetralone inhibits cancer cell proliferation and migration, and induces hepatocellular carcinoma cell (HCC) apoptosis. 7-Methoxy-1-tetralone decreased the protein levels of NF-κB, matrix metallopeptidase 2 (MMP2)/MMP9, and p-AKT. 7-Methoxy-1-tetralone showed antitumor activity in nude mice and had no effect on body weight and liver, spleen and organ index[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> PI3K/Akt/mTOR >> Akt

Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> c-Met/HGFR

[In Vitro]

7-Methoxy-1-tetralone (31.25-1000 μM; 48 h) 抑制 LO2 和 HepG2 细胞的增殖活性[1]。 7-Methoxy-1-tetralone (40 μM, 100 μM, 250 μM; 48 h) 诱导 HepG2 细胞凋亡，调节细胞中 c-Met、p-AKT、AKT、NF-κB、MMP2、MMP9 蛋白的表达水平[1]。 Western Blot Analysis[1] Cell Line: HepG2 cells Concentration: 40 μM, 100 μM, and 250 μM Incubation Time: 48 h Result: Decreased the protein expression levels of c-Met, p-AKT, NF-κB, MMP2, and MMP9. Cell Proliferation Assay[1] Cell Line: LO2 and HepG2 cells Concentration: 31.25 μM, 62.5 μM, 125 μM, 250 μM, 500 μM, and 1000 μM Incubation Time: 24 h, 48 h, and 72 h Result: Exhibited anti-proliferative activity of MT on LO2 and HepG2 cells.

[In Vivo]

7-Methoxy-1-tetralone (80, 120, or 160 mg/kg/d；腹腔注射；共 19 次剂量) 抑制 HepG2 细胞皮下植入肿瘤模型的肿瘤生长[1]。 Animal Model: BALB/c nude mice (5-week-old) with subcutaneously implanted HepG2 cells[1] Dosage: 80, 120, or 160 mg/kg/d Administration: Intraperitoneal injection; sacrificed after 19 days Result: Resulted the tumor inhibition rates of 40.57% (80 mg/kg), 51.43% (120 mg/kg), 79.43% (160 mg/kg), respectively.

[References]

[1]. Wen Y, et al. 7-Methoxy-1-Tetralone Induces Apoptosis, Suppresses Cell Proliferation and Migration in Hepatocellular Carcinoma via Regulating c-Met, p-AKT, NF-κB, MMP2, and MMP9 Expression. Front Oncol. 2020 Feb 7;10:58.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
312.3±31.0 °C at 760 mmHg

[ Melting Point ]:
59-63 °C(lit.)

[ Molecular Formula ]:
C₁₁H₁₂O₂

[ Molecular Weight ]:
176.21

[ Flash Point ]:
145.8±18.4 °C

[ Exact Mass ]:
176.083725

[ PSA ]:
26.30000

[ LogP ]:
2.79

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.549

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

The reaction of 1-tetralones with thallium trinitrate supported on clay: ring contraction vs alpha-oxidation. Ferraz H, et al.

J. Braz. Chem. Soc. 12(5) , 680-684, (2001)

Substituted Derivatives of 3a, 4, 5, 6-Tetrahydrosuccinimido [3, 4-b] Acenaphthen-10-one. Campaigne E and Weddleton RF.

Proc. Indian Acad. Sci. A 95 , (2013)

13H-benzo [6-7] indolo [3, 2-c] quinolines (B [6, 7] IQ): optimization of their DNA triplex-specific stabilization properties. Schmitt P, et al.

Chem. Commun. (Camb.) 9 , 763-764, (2000)