83280-65-3

Basic information

• Product Name: 2-Acetylfuro-1,4-naphthoquinone
• Synonyms: 2-Acetylfuro-1,4-naphthoquinone;Naphtho[2,3-b]furan-4,9-dione, 2-acetyl-;Napabucasin;2-Acetylfuro-1,4-phthoquinone;Napabucasin (BBI608);2-acetylnaphtho[2,3-b]furan-4,9-quinone;Remimazolam besylate
• CAS NO: 83280-65-3
• Molecular Formula: C14H8O4
• Molecular Weight: 240.21092
• Mol File: 83280-65-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 225-226℃ (dichloromethane )
• Boiling Point: 444.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.385±0.06 g/cm3(Predicted)
• Storage Temp.: +2C to +8C
• Solubility: Soluble in DMSO (up to 20 mg/ml)
• 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.
• CAS DataBase Reference: 2-Acetylfuro-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetylfuro-1,4-naphthoquinone(83280-65-3)
• EPA Substance Registry System: 2-Acetylfuro-1,4-naphthoquinone(83280-65-3)

Safety Data

• Hazardous Substances Data: 83280-65-3(Hazardous Substances Data)

Usage

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.

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

Upstream product

• 13019-43-7 2-isopropylnaphtho[2,3-b]furan-4,9-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 25109-57-3 3,4-dibromobutan-2-one 
• 78-94-4 methyl vinyl ketone 
• 75-16-1 methylmagnesium bromide 
• 1203-39-0 3-bromolawsone 
• 15441-75-5 2-ethynyl-2-methyl-1,3-dioxolane 
• 130-15-4 [1,4]naphthoquinone 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 
• 18633-71-1 2-ethyl-4H,9H-naphtho[2,3-b]furan-4,9-dione 
• 155622-69-8 bromomethyl vinyl ketone 
• 61203-01-8 3-bromobut-3-en-2-one 
• 117560-06-2 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide 
• 84-79-7 Lapachol 

Downstream Products

• 83889-95-6 2-(1-hydroxy-ethyl)-naphtho[2,3-b]furan-4,9-dione 

Relevant articles and documents

FURANONAPHTHOQUINONES FROM TABEBUIA OCHRACEA

From the trunkwood of Tabebuia ochracea, β-sitosterol, cycloolivil, lapachol, and seven furanonaphthoquinones including the known 2-(1-hydroxyethyl)naphthofuran-4,9-quinone were isolated.The six new furanonaphthoquinones comprise three similar C2 alcohol-ketone pairs at C-2 as proved by oxidations with pyridinium chlorochromate. 2-Acetyl-6-methoxynaphthofuran-4,9-quinone was shown to be different from the synthetic 7-methoxy isomer, while 2-acetyl-8-methoxynaphthofuran-4,9-quinone and 2-acetyl-7,8-dimethoxynaphthofuran-4,9-quinone were identical to the synthetic compounds.

Conjugates Derived from Lapatinib Derivatives with Cancer Cell Stemness Inhibitors Effectively Reversed Drug Resistance in Triple-Negative Breast Cancer

Increasing evidence indicates that the cancer stem cell (CSC) subpopulation contributes to the therapeutic resistance and metastasis of tumors, leading to patient recurrence and death. Herein, we designed and synthesized several compounds by conjugating lapatinib derivatives with different CSC inhibitors to treat with lapatinib-induced MDA-MB-231 drug-resistant cells. In vitro biological studies indicated that 3a showed strong cytotoxicity and EGFR enzyme inhibitory activity and effectively reversed lapatinib-mediated resistance of MDA-MB-231 cells via inhibiting triple-negative breast cancer (TNBC) cell stemness and the AKT/ERK signaling pathway. In addition, 3a was capable of strongly suppressing the invasion and migration of TNBC cells by inhibiting the Wnt/β-catenin signaling pathway and MMP-2 and MMP-9 protein expression. In vivo tumorigenicity tests showed that 3a could inhibit the occurrence of TNBC by inhibiting BCSCs, proving 3a is a potential EGFR and CSC dual inhibitor for TNBC treatment.

METHOD FOR PRODUCING 2-ALKYLCARBONYLNAPHTHO[2,3-b]FURAN-4,9-DIONE-RELATED SUBSTANCE, AND SAID RELATED SUBSTANCE

Provided is a method for producing a 2-alkylcarbonylnaphtho[2,3-b]furan-4,9-dione-related substance, which is suitable for the production on an industrial scale. The present invention provides: a method for producing an intermediate for the production of