4496-30-4

Basic information

• Product Name: 1H-naphtho[2,3-d]imidazole-4,9-dione
• CAS NO: 4496-30-4
• Molecular Formula: C₁₁H₆N₂O₂
• Molecular Weight: 198.1775
• Mol File: 4496-30-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 520.5°C at 760 mmHg
• Flash Point: 263.1°C
• Density: 1.517g/cm³
• Vapor Pressure: 6.2E-11mmHg at 25°C
• Refractive Index: 1.712
• CAS DataBase Reference: 1H-naphtho[2,3-d]imidazole-4,9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-naphtho[2,3-d]imidazole-4,9-dione(4496-30-4)
• EPA Substance Registry System: 1H-naphtho[2,3-d]imidazole-4,9-dione(4496-30-4)

Safety Data

• Hazardous Substances Data: 4496-30-4(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic

Structure

Naphtalene ring fused with an imidazole ring

Usage

Production of dyes and pigments, building block in organic synthesis, potential applications in pharmaceutical industry and organic electronic devices and materials.

Upstream product

• 13755-96-9 2-acetamido-3-amino-1,4-naphthoquinone 
• 122-51-0 orthoformic acid triethyl ester 
• 50-00-0 formaldehyd 
• 13755-95-8 2,3-diamino-1,4-naphthoquinone 
• 64-18-6 formic acid 
• 5397-78-4 2-acetamido-3-chloro-1,4-naphthoquinone 
• 2797-51-5 quinoclamine 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 771-97-1 2,3-Diaminonaphthalene 
• 269-07-8 naphtho[2,3-d]imidazole 

Downstream Products

• 15030-17-8 1-phenyl-1H-naphtho[2,3-d]imidazole-4,9-dione 

Relevant articles and documents

Synthesis and biological evaluation of naphthoquinone phenacylimidazolium derivatives

In order to expand structural diversity and improve antitumor efficiency, forty new naphthoquinone phenacylimidazolium derivatives were designed, synthesized and evaluated. Good synthetic yields were obtained under mild conditions using easily available starting materials. Cytotoxicity of these compounds was evaluated in vitro against a panel of human tumor cell lines: human breast carcinoma cell lines (MCF-7), human cervical carcinoma cell lines (HeLa), and human lung carcinoma cell lines (A549). Among them, the optimal compound 7m showed splendid antiproliferative activity with low to 50 nM IC50 values against MCF-7 and excellent selectivity of 256-fold compared with the normal cell lines L929. Compound 7m induced apoptosis in a dose-dependent manner. Further mechanism experiments showed that compound 7m dramatically inhibited the expression of survivin and activated the pro-apoptotic protein caspase-3. Our results indicated that the structural modification on the 1,3-substituents of naphthoquinone imidazoliums without 2-substituent is also promising to obtain new antitumor compounds.

Design, synthesis and biological evaluation of novel naphthoquinone derivatives as IDO1 inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) mediated kynurenine pathway of tryptophan degradation is identified as an appealing and novel target in immunotherapy for the treatment of cancer. In this study, a novel series of naphthoquinone derivatives were synthesized, characterized and evaluated for their inhibitory activities against IDO1, and their structure?activity relationship was investigated. Among them, compounds T16, T44, T47, T49, T53 and T54 displayed potent IDO1 inhibitory activities with IC50 values ranging between 18 and 61 nM, which are more potent than INCB024360 undergoing clinical trial III evaluation. In addition, compounds T28, T44 and T53 decreased the kynurenine levels in rat plasma by 30%–50%. Compounds exhibiting excellent IDO1 inhibitory activities were also evaluated for their inhibitory activities against tryptophan 2,3-dioxygenase (TDO). Of which, compound T28 (IDO1 IC50 = 120 nM) showed promising TDO inhibition (IC50 72 nM) and was identified as an IDO1/TDO dual inhibitor.