58472-36-9

Usage

Uses

Used in Pharmaceutical Synthesis:
7-fluoro-2-hydroxynaphthalene-1,4-dione is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with improved properties.
Used in Organic Compounds Synthesis:
As a valuable building block in organic chemistry, 7-fluoro-2-hydroxynaphthalene-1,4-dione is used in the synthesis of various functional materials, enhancing the range of organic compounds available for different applications.
Used in Organic Light-Emitting Diodes (OLEDs):
Leveraging its fluorescent properties, 7-fluoro-2-hydroxynaphthalene-1,4-dione is used as a component in the development of organic light-emitting diodes, contributing to the advancement of display and lighting technologies.
Used as a Fluorescent Probe in Research:
7-fluoro-2-hydroxynaphthalene-1,4-dione is utilized as a fluorescent probe in biological and environmental monitoring applications, providing a tool for researchers to track and monitor various processes and substances effectively.

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

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

Relevant academic research and scientific papers

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

Suppression of Drug-Resistant Non-Small-Cell Lung Cancer with Inhibitors Targeting Minichromosomal Maintenance Protein

Drug resistance has been a major threat in cancer therapies that necessitates the development of new strategies to overcome this problem. We report here a cell-based high-throughput screen of a library containing two-million molecules for the compounds that inhibit the proliferation of non-small-cell lung cancer (NSCLC). Through the process of phenotypic screening, target deconvolution, and structure-activity relationship (SAR) analysis, a compound of furanonaphthoquinone-based small molecule, AS4583, was identified that exhibited potent activity in tyrosine kinase inhibitor (TKI)-sensitive and TKI-resistant NSCLC cells (IC50 = 77 nM) and in xenograft mice. The mechanistic studies revealed that AS4583 inhibited cell-cycle progression and reduced DNA replication by disrupting the formation of the minichromosomal maintenance protein (MCM) complex. Subsequent SAR study of AS4583 gave compound RJ-LC-07-48 which exhibited greater potency in drug-resistant NSCLC cells (IC50 = 17 nM) and in mice with H1975 xenograft tumor.

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.

Synthesis and biological evaluation of β-lapachone-monastrol hybrids as potential anticancer agents

A series of novel β-lapachone analogs was designed and synthesized by replacing pyran ring of β-lapachone with tetrahydropyrimidinethione moiety of monastrol. These hybrids had potent antiproliferative activity against NQO1-rich cell lines (HepG2 and A549

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.

NAPTHOQUINONES, PRO-DRUGS, AND METHODS OF USE THEREOF

Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R1, R2, R3, R4, R5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

4,9-DIOXO-4,9-DIHYDRONAPHTHO(2,3-B)FURAN-3-CARBOXMIDE DERIVATIVES AND USES THEREOF FOR TREATING PROLIFERATIVE DISEASES AND INFECTIOUS DISEASES

The present disclosure provides compounds of Formulas (I), (II), and pharmaceutically acceptable salts thereof. The compounds described herein are useful in treating proliferative diseases, for example, cancer (e.g., lung cancer), and infectious diseases (e.g., bacterial infections).

Identification of β-lapachone analogs as novel MALT1 inhibitors to treat an aggressive subtype of diffuse large B-cell lymphoma

The treatment of activated B cell-like DLBCL (ABC-DLBCL) is one of the urgent unmet medical needs because it is the most resistant DLBCL subtype to current therapies eagerly awaiting effective therapeutic strategies. Recently, the paracaspase MALT1 has emerged as a promising therapeutic target for the treatment of ABC-DLBCL. Herein, we report a new class of MALT1 inhibitors developed by high-throughput screening and structure-based drug design. The original hit, 4-amino-1,2-naphthoquinone series inhibited MALT1 activity but suffered from poor cellular activity. The extensive pharmacophore search led to the discovery of structurally similar β-lapachone that is a direct inhibitor of MALT1 and possesses favorable physicochemical properties. Molecular simulation studies suggested the possibility of the formation of a covalent bond between MALT1 and β-lapachone, which was corroborated by experimental wash-out studies. Inspired by this, we explored the structure-activity relationships by incorporating electron-withdrawing substituents at C8 position of β-lapachone. These MALT1 inhibitors exhibited potent antiproliferative activity to OCI-LY3 cell line and inhibited the cleavage of CYLD mediated MALT1.

Synthesis and antiallergic activity of 2 hydroxy 3 nitro 1,4 naphthoquinones

A selection of novel 2-hydroxy-3-nitro-1,4-naphthoquinones are shown to be potent inhibitors of rat passive cutaneous anaphylaxis (PCA) and to have highest potency with alkyl substitution at both C-6 and C-7. The most potent compounds were 7c and 7e which produced a 50% inhibition in the rat PCA test at doses of about 10 μM/kg following subcutaneous administration and showed activity after oral administration. Related 4-hydroxy-3-nitro-2(1H)-naphthalenones had no effect on rat PCA in doses up to 500 μM/kg.