ChemicalBook--->CAS DataBase List--->83280-65-3

83280-65-3

83280-65-3 Structure

83280-65-3 Structure
IdentificationBack Directory
[Name]

2-Acetylfuro-1,4-naphthoquinone
[CAS]

83280-65-3
[Synonyms]

139057
CS-945
BBI-606
Napabucasin
Napabucasin (BBI608)
Remimazolam besylate
Napabucasin Impurity
2-Acetylfuro-1,4-phthoquinone
2-Acetylfuro-1,4-naphthoquinone
2-acetylbenzo[f][1]benzofuran-4,9-dione
2-acetylnaphtho[2,3-b]furan-4,9-quinone
Naphtho[2,3-b]furan-4,9-dione, 2-acetyl-
Cancer Stemness Inhibitor, BBI608 - CAS 83280-65-3 - Calbiochem
[Molecular Formula]

C14H8O4
[MDL Number]

MFCD28155270
[MOL File]

83280-65-3.mol
[Molecular Weight]

240.211
Chemical PropertiesBack Directory
[Melting point ]

225-226℃ (dichloromethane )
[Boiling point ]

444.4±45.0 °C(Predicted)
[density ]

1.385±0.06 g/cm3(Predicted)
[storage temp. ]

+2C to +8C
[solubility ]

Soluble in DMSO (up to 20 mg/ml)
[form ]

Brown solid
[color ]

Yellow
[λmax]

272nm(EtOH)(lit.)
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
[InChI]

InChI=1S/C14H8O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-6H,1H3
[InChIKey]

DPHUWDIXHNQOSY-UHFFFAOYSA-N
[SMILES]

O1C(C(C)=O)=CC2C(=O)C3=C(C(=O)C1=2)C=CC=C3
Safety DataBack Directory
[WGK Germany ]

WGK 3
[HS Code ]

2932.99.7000
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

Napabucasin is an inhibitor of cancer cell stemness. It reduces growth in a panel of cancer cells enriched for high stemness (IC50s = 0.291-1.249 μM) and decreases protein and gene expression of various self-renewal and pro-survival markers including Nanog, Smo, Axl, Atm, and Bmi-1 in a concentration-dependent manner in FaDu head and neck squamous cell carcinoma (HNSCC) cells. In vivo, napabucasin (20 mg/kg per day) inhibits tumor growth in a PaCa-2 mouse xenograft model and prevents tumor regrowth after cessation of treatment. It blocks formation of spleen and liver metastases in an HT29 intrasplenic nude mouse model system (ISMS) model. Napabucasin (40 mg/kg, i.p.) also reduces tumor volume in PC3 and 22RV1 prostate cancer mouse xenograft models.
[Uses]

Napabucasin is a cancer cell stemness inhibitor which attenuates the progression of prostate cancer.
[in vivo]

Napabucasin (40 mg/kg) or Docetaxel significantly reduces xenograft tumor growth and tumor volume (TV) compared with PBS (P<0.05). Notably, while no differences are observed between the Napabucasin and the docetaxel groups in PC-3 mouse xenograft models, the TV in Napabucasin group is even lower than docetaxel group in 22RV1 mouse xenograft models (P<0.05). Additionally, Napabucasin or docetaxel also significantly reduces tumor weight compared with PBS (P<0.05)[1].

[IC 50]

STAT3
[storage]

Store at -20°C
[References]

1) Li et al. (2015), Suppression of cancer relapse and metastasis by inhibiting cancer stemness; Proc. Natl. Acad. Sci. USA, 112 1839 2) Hubbard and Grothey (2017), Napabucasin: an Update on the First-in-Class Cancer Stemness Inhibitor; Drugs, 77 1091 3) Zhang et al. (2016), Suppression of prostate cancer progression by cancer cell stemness inhibitor napabucasin; Cancer Med., 5 1251 4) MacDonagh et al. (2018), BBI608 inhibits cancer stemness and reverses cisplatin resistance in NSCLC; Cancer Lett., 428 117
Spectrum DetailBack Directory
[Spectrum Detail]

2-Acetylfuro-1,4-naphthoquinone(83280-65-3)1HNMR
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