97620-82-1

Basic information

• Product Name: 3-HYDROXYBENZO[B]NAPHTHO[2,3-D]FURAN-6,11-DIONE
• Synonyms: 3-HYDROXYBENZO[B]NAPHTHO[2,3-D]FURAN-6,11-DIONE
• CAS NO: 97620-82-1
• Molecular Formula: C16H8O4
• Molecular Weight: 264.23
• Product Categories: pharmacetical
• Mol File: 97620-82-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 362.5°Cat760mmHg
• Flash Point: 173.1°C
• Appearance: /
• Density: 1.515g/cm³
• Vapor Pressure: 9.2E-06mmHg at 25°C
• Refractive Index: 1.744
• CAS DataBase Reference: 3-HYDROXYBENZO[B]NAPHTHO[2,3-D]FURAN-6,11-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYBENZO[B]NAPHTHO[2,3-D]FURAN-6,11-DIONE(97620-82-1)
• EPA Substance Registry System: 3-HYDROXYBENZO[B]NAPHTHO[2,3-D]FURAN-6,11-DIONE(97620-82-1)

Safety Data

• Hazardous Substances Data: 97620-82-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H8O4/c17-8-5-6-11-12(7-8)20-16-13(11)14(18)9-3-1-2-4-10(9)15(16)19/h1-7,17H

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 108-46-3 recorcinol 

Relevant articles and documents

Synthesis, cytotoxicity, and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones

Benzofuroquinolinediones (7c and 7d) were synthesized by base-catalyzed condensation of dichloroquinolinediones with phenolic derivatives. Their dialkylaminoalkoxy derivatives (8i-8p) were prepared by reaction with various dialkylaminoalkyl chlorides. The cytotoxicity of the synthesized compounds was evaluated against eight types of human cancer cell lines, and their topoisomerase II inhibition was assessed. In general, the cytotoxicity of benzofuroquinolinediones (8i-8p) was similar or superior to that of doxorubicin and showed more potent inhibitory activity than naphthofurandiones (8a-8h). Also, most of the compounds exhibited excellent topoisomerase II inhibitory activity at a concentration of 5 μM and two compounds, 8d and 8i, showed IC50 values of 1.19 and 0.68 μM, respectively, and were much more potent than etoposide (IC50 = 78.4 μM), but similar to doxorubicin (IC50 = 2.67 μM). However their inhibitory activity on topoisomerase I was lower, and 8d and 8i showed IC50 values of 42.0 and 64.3 μM, respectively.

Synthesis, in vitro and in vivo activity of benzophenone-based inhibitors of steroid sulfatase

Steroid sulfatase (STS) is an important new therapeutic target in oncology. Attempts to design nonsteroidal STS inhibitors, because of the oestrogenicity of the original lead oestrone 3-O-sulfamate in rodents, have led to the discovery of benzophenone-4,4′-O,O-bis-sulfamate (BENZOMATE, 3). The nonfused bicyclic BENZOMATE is a highly potent STS inhibitor in vitro, inhibiting STS activity in intact MCF-7 breast cancer cells by >70% at 0.1μM and in placental microsomes by >98% at 10μM. When MCF-7 cells were pre-treated with 3 at 1μM and then washed to remove unbound inhibitor, the initial 94% inhibition was reduced to 89% suggesting that 3, like other sulfamate-based STS inhibitors, inhibits the enzyme irreversibly. This agent also inhibits rat liver STS activity by 84% and 93% respectively 24h after a single dose of 1 or 10mg/kg, demonstrating that BENZOMATE possesses similar in vivo potency to the established potent nonsteroidal inhibitor 667COUMATE. Several modifications were made to BENZOMATE structurally and effects on in vitro activity were examined. These structure-activity relationship studies show that its carbonyl and bis-sulfamate groups are pivotal for activity, although conformational flexibility is not required. Two rigid anthraquinone-based sulfamate derivatives however showed inhibitory activity significantly better than BENZOMATE in the MCF-7 cell assay. BENZOMATE and related analogues therefore represent an important class of non-steroidal STS inhibitor and lead compounds for future drug design.