4572-59-2

Basic information

• Product Name: 1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione
• Synonyms: 1H-naphth[2,3-d]imidazole-4,9-dione, 1,2-dimethyl-
• CAS NO: 4572-59-2
• Molecular Formula: C₁₃H₁₀N₂O₂
• Molecular Weight: 226.2307
• Mol File: 4572-59-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 469.9°C at 760 mmHg
• Flash Point: 238°C
• Density: 1.37g/cm³
• Vapor Pressure: 5.31E-09mmHg at 25°C
• Refractive Index: 1.692
• CAS DataBase Reference: 1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione(4572-59-2)
• EPA Substance Registry System: 1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione(4572-59-2)

Safety Data

• Hazardous Substances Data: 4572-59-2(Hazardous Substances Data)

Usage

Class

Naphthoimidazoles

Molecular Structure

Complex

Potency

Potent antitumor agent

Potential Use

Cancer treatment

Specific Cancers

Leukemia and solid tumors

Activity

Exhibits cytotoxic activity against various cancer cell lines

Preclinical Studies

Shown promise

Additional Investigation

Potential as a photosensitizer in photodynamic therapy

Photodynamic Therapy

Treatment using light-sensitive drugs to destroy cancer cells

Ongoing Research

Exploring therapeutic potential and applications in medical science

Upstream product

• 156904-71-1 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho<2,3-d>imidazol-4,9-dione 
• 2797-51-5 quinoclamine 
• 54010-92-3 NSC₁₃₀₄₄₀ 
• 156904-74-4 2-chloroacetylamino-3-methylamino-1,4-naphthoquinone 
• 1792-36-5 1H-2-methylnaphtho[2,3-d]imidazole 
• 771-97-1 2,3-Diaminonaphthalene 
• 71675-75-7 1,2-dimethyl-1H-naphtho-[2,3-d]imidazole 
• 15252-69-4 2-chloro-1,4-dihydro-3-methylamino-1,4-dioxonaphthalene 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 5397-78-4 2-acetamido-3-chloro-1,4-naphthoquinone 
• 1676-56-8 N-[3-(methylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]acetamide 

Relevant articles and documents

Preparation and in vitro antiprotozoan activity of new naphthoimidazolediones

The original compound bearing the coplanar quinone and imidazole systems, 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho[2,3-d] imidazol-4,9-dione reacted with various nitronate anions to afford, in moderate to rood yields, new naphtho- imidazolediones bearing a trisubstituted ethylenic double bond at the 2-position. These compounds were evaluated as potential antiprotozoan agents. Some derivatives were found to have a significant activity, but the naphthoquinone was found to be a less efficient pharmacophore than the nitro group.

Antimalarial N1, N3-Dialkyldioxonaphthoimidazoliums: Synthesis, Biological Activity, and Structure-activity Relationships

Here we report the nanomolar potencies of N1,N3-dialkyldioxonaphthoimidazoliums against asexual forms of sensitive and resistant Plasmodium falciparum. Activity was dependent on the presence of the fused quinone-imidazolium entity and lipophilicity imparted by the N1/N3 alkyl residues on the scaffold. Gametocytocidal activity was also detected, with most members active at IC50 1 μM. A representative analog with good solubility, limited PAMPA permeability, and microsomal stability demonstrated oral efficacy on a humanized mouse model of P. falciparum.

Use of tricyclic derivatives of 1,4-dihydro-1,4-dioxo-1H-naphthalene, novel compounds obtained and their application in theraphy

The invention concerns the therapeutic use of tricyclic salts and their pharmaceutically acceptable salts having the general formula: in which: A is either a sulfur atom, an oxygen atom, or an R3N radical where R3is a hydrogen atom,