4572-59-2

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 academic research and scientific papers

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.

Synthesis and biological activity of imidazole based 1,4-naphthoquinones

Design and development of drugs in multi-drug resistant (MDR) infections have been of growing interest. We report the syntheses, and antibacterial and antifungal activities of imidazole-based 1,4-naphthoquinones (I-1toI-4; 1-alkyl-2-methyl-1H-naphtho[2,3-d]imidazole-4,9-dione (alkyl = methyl to butyl)) and their precursors (B-3;N-(3-chloro-1,-dioxo-1,4-dihydronaphthalen-2-yl)acetamide) andA-1toA-4;N-(3-(alkylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide (alkyl = methyl to butyl). Crystal structures ofB-3A-1toA-3andI-2toI-4were obtained through single crystal X-ray diffraction experiments. Electronic structure and charge distribution have further been characterized with the use of Density Functional Theory. Seven of these derivatives display a broad spectrum of antibacterial activity against few selected bacterial strains (Gram-positive and Gram-negative). As demonstrated MIC values withB-2andB-3against bacterial isolates were 8-64 μg ml?1and those against pathogenic yeast,C. albicans, were observed in the range of 128-256 μg ml?1. MIC data of these derivatives suggest them to be promising against pathogens.

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.

Oxidation products of fused 2-hetarylimidazole derivatives

Oxidation of 5-(1-methyl-1H-benzimidazol-2-yl)thiophene-, and -selenophene-2-carbaldehydes with potassium dichromate in 20% aqueous sulfuric acid afforded the corresponding carboxylic acids. Analogous reaction with 5-(1-methyl-1H-benzimidazol-2-yl)furan-2-carbaldehyde led to the formation of 1- methyl-1H-benzimidazole as a result of decarboxylation of the primary oxidation product and subsequent decomposition of the furan ring. Probable factors responsible for instability of 5-(1H-benzimidazol-2-yl)- hetarene-2-carboxylic acids were considered. The oxidation of 2-furylnaphtho[2,3-d]- and 2-hetarylphenanthro- [9,10-d]imidazoles gave, respectively, an anthraquinone analog and 6,7-quinones. ?-Electron-rich heterocycles in 2-furyl- and 2-pyrrolylphenanthro[9,10-d]imidazoles were oxidized completely, being replaced by hydrogen. Pleiades Publishing, Ltd., 2011.

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,