58472-36-9

Basic information

• Product Name: 7-fluoro-2-hydroxynaphthalene-1,4-dione
• Synonyms: 1,4-naphthalenedione, 7-fluoro-2-hydroxy-; 7-Fluoro-2-hydroxy-1,4-naphthoquinone
• CAS NO: 58472-36-9
• Molecular Formula: C₁₀H₅FO₃
• Molecular Weight: 192.1433
• Mol File: 58472-36-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 363.646°C at 760 mmHg
• Flash Point: 173.727°C
• Appearance: /
• Density: 1.578g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 7-fluoro-2-hydroxynaphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 7-fluoro-2-hydroxynaphthalene-1,4-dione(58472-36-9)
• EPA Substance Registry System: 7-fluoro-2-hydroxynaphthalene-1,4-dione(58472-36-9)

Safety Data

• Hazardous Substances Data: 58472-36-9(Hazardous Substances Data)

Usage

General Description

7-fluoro-2-hydroxynaphthalene-1,4-dione is a chemical compound with the molecular formula C10H5FO3. It is a derivative of naphthalene and is commonly used in the synthesis of pharmaceuticals and organic compounds. This chemical is known for its fluorescent properties and has been studied for its potential application in organic light-emitting diodes (OLEDs). Additionally, 7-fluoro-2-hydroxynaphthalene-1,4-dione has been investigated for its potential use as a fluorescent probe in biological and environmental monitoring applications. It is considered a valuable building block in organic chemistry and is commonly used as a precursor in the synthesis of various functional materials.

InChI:InChI=1/C10H5FO3/c11-5-1-2-6-7(3-5)10(14)9(13)4-8(6)12/h1-4,13H

Upstream product

• 703-67-3 6-fluoro-3,4-dihydronaphthalen-1(2H)-one 
• 589-06-0 4-(4-fluorophenyl)butanoic acid 
• 2840-44-0 7-fluoro-3,4-dihydronaphthalen-1(2H)-one 

Relevant articles and documents

Design, synthesis, and biological evaluation of 3-(1-benzotriazole)-nor-β-lapachones as NQO1-directed antitumor agents

A series of novel 3-(1-benzotriazole)-nor-β-lapachones 5a–5l were synthesized as the NQO1-targeted anticancer agents. Most of these compounds displayed good antiproliferative activity against the breast cancer MCF-7, lung cancer A549 and hepatocellular ca

Bifunctional Naphtho[2,3- d][1,2,3]triazole-4,9-dione Compounds Exhibit Antitumor Effects in Vitro and in Vivo by Inhibiting Dihydroorotate Dehydrogenase and Inducing Reactive Oxygen Species Production

Human dihydroorotate dehydrogenase (hDHODH) is an attractive target for cancer therapy. Based on its crystal structure, we designed and synthesized a focused compound library containing the structural moiety of 1,4-benzoquinone, which possesses reactive oxygen species (ROS) induction capacity. Compound 3s with a naphtho[2,3-d][1,2,3]triazole-4,9-dione scaffold exhibited inhibitory activity against hDHODH. Further optimization led to compounds 11k and 11l, which inhibited hDHODH activity with IC50 values of 9 and 4.5 nM, respectively. Protein-ligand cocrystal structures clearly depicted hydrogen bond and hydrophobic interactions of 11k and 11l with hDHODH. Compounds 11k and 11l significantly inhibited leukemia cell and solid tumor cell proliferation and induced ROS production, mitochondrial dysfunction, apoptosis, and cell cycle arrest. Nanocrystallization of compound 11l displayed significant in vivo antitumor effects in the Raji xenograft model. Overall, this study provides a novel bifunctional compound 11l with hDHODH inhibition and ROS induction efficacy, which represents a promising anticancer lead worthy of further exploration.

AZIRIDINYL AND AMINO DIMERIC NAPHTHOQUINONE COMPOUNDS AND USE FOR ACUTE MYELOID LEUKEMIA

The invention relates to new amino dimeric naphthoquinone compounds with antileukemic activity. Compounds of the invention demonstrated increased aqueous solubility compared to previously available dimeric naphthoquinones and potent nanomolar inhibition of cell survival in AML cells. Preferred compounds contained an aziridine or a secondary amino alcohol pharmacophore.