7251-00-5

Usage

Uses

Used in Pharmaceutical Industry:
2-nitro-10H-acridin-9-one is used as an active pharmaceutical ingredient for its anti-inflammatory and analgesic effects, providing relief from pain and reducing inflammation in various medical conditions.
Used in Dye Production:
2-nitro-10H-acridin-9-one is used as a key intermediate in the synthesis of dyes, contributing to the development of vibrant and stable colorants for various applications.
Used in Fluorescent Material Production:
2-nitro-10H-acridin-9-one is used as a component in the production of fluorescent materials, taking advantage of its photophysical properties to create materials with specific light-emitting characteristics.
Used in Molecular Imaging and Fluorescence Microscopy:
2-nitro-10H-acridin-9-one is used as a fluorescent probe in molecular imaging and fluorescence microscopy, enabling the visualization and tracking of biological processes at the molecular level.

InChI:InChI=1/C13H8N2O3/c16-13-9-3-1-2-4-11(9)14-12-6-5-8(15(17)18)7-10(12)13/h1-7H,(H,14,16)

Upstream product

• 29808-81-9 2-Nitroacridine 
• 89459-28-9 7-nitro-9,10-dihydro-9-oxo-4-acridine carboxylic acid 
• 6237-22-5 3-nitro-9-(3'-dimethylaminopropylamino)acridine 
• 108-86-1 bromobenzene 
• 56946-45-3 2-Anilino-5-nitrobenzoyl-chlorid 
• 616-79-5 2-amino-5-nitro-benzoic acid 
• 578-95-0 10H-acridin-9-one 
• 100-01-6 4-nitro-aniline 
• 62-53-3 aniline 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 
• 24782-64-7 9-Oxoacridan-4-carboxylic acid 
• 97741-93-0 1,7-dinitroacridinone 
• 40239-75-6 1-nitro-9-acridanone 
• 260-94-6 acridine 

Downstream Products

• 581-28-2 2-aminoacridine 
• 58658-02-9 10-methyl-2-nitroacridin-9(10H)-one 
• 58658-03-0 2-amino-10-methyl-9-acridanone 
• 22817-17-0 acridin-2-ol 
• 27918-14-5 2-aminoacridone 
• 61639-26-7 9,10-dihydro-acridin-2-ylamine 
• 776299-27-5 2-(p-acetylaminobenzenesulphonylamino)-acridone 
• 676456-13-6 2-(p-aminobenzenesulphonylamino)acridone 

Relevant academic research and scientific papers

SULFONATED 2(7)-AMINOACRIDONE AND 1-AMINOPYRENE DYES AND THEIR USE AS FLUORESCENT TAGS, IN PARTICULAR FOR CARBOHYDRATE ANALYSIS

Sulfonated 2(7)-aminoacridone and 1-aminopyrene dyes and their use as fluorescent tags, in particular for carbohydrate analysis The invention relates to fluorescent dyes with multiple negatively charged groups in their ionized form which are aminoacridone

Fluorescent nitric oxide donor for the detection and killing of: Pseudomonas aeruginosa

The epidemic of multidrug-resistant bacteria calls for the improvement of both detection methods for bacterial infections and methods of treatment. Nitric oxide is a known potent antibacterial agent, but due to its gaseous and highly reactive nature, it is difficult to incorporate into a stable antibacterial compound. In this paper, we synthesize a nitric oxide donor attached to a fluorescent compound, creating a material that can both detect and kill the deadly multi-drug resistant bacteria strain Pseudomonas aeruginosa. Detection occurs through a bacterial enzyme-activated color change, showing a clear and obvious change from blue to yellow under UV light. The synthesized compound spontaneously releases 853 μmol of nitric oxide/g from a 10 mM initial concentration. Antibacterial efficacy studies after exposing Pseudomonas aeruginosa to a 10 mM dose of the synthesized compound show a 55-75% reduction in bacteria after 24 hours. This work is the first instance of a small molecule dual-function material that can both detect and kill bacteria.

Improving the fluorescent probe acridonylalanine through a combination of theory and experiment

Acridonylalanine (Acd) is a useful fluorophore for studying proteins by fluorescence spectroscopy, but it can potentially be improved by being made longer wavelength or brighter. Here, we report the synthesis of Acd core derivatives and their photophysical characterization. We also performed ab initio calculations of the absorption and emission spectra of Acd derivatives, which agree well with experimental measurements. The amino acid aminoacridonylalanine (Aad) was synthesized in forms appropriate for genetic incorporation and peptide synthesis. We show that Aad is a superior F?rster resonance energy transfer acceptor to Acd in a peptide cleavage assay and that Aad can be activated by an aminoacyl tRNA synthetase for genetic incorporation. Together, these results show that we can use computation to design enhanced Acd derivatives, which can be used in peptides and proteins.

Potent acetylcholinesterase inhibitors: Synthesis, biological assay and docking study of nitro acridone derivatives

The reaction of o-halobenzoic acid with aniline derivatives and their subsequent cyclization reaction yielded the acridone derivatives. The series of nitro acridone derivatives were prepared by Ullmann condensation in presence of copper as catalyst and we

Evaluation of synthetic acridones and 4-quinolinones as potent inhibitors of cathepsins L and v

Cathepsins, also known as lysosomal cysteine peptidases, are members of the papain-like peptidase family, involved in different physiological processes. In addition, cathepsins are implicated in many pathological conditions. This report describes the synthesis and evaluation of a series of N-arylanthranilic acids, acridones, and 4-quinolinones as inhibitors of cathepsins V and L. The kinetics revealed that compounds of the classes of acridones are reversible competitive inhibitors of the target enzyme with affinities in the low micromolar range. They represent promising lead candidates for the discovery of novel competitive cathepsin inhibitors with enhanced selectivity and potency. On the other hand, 4-quinolinones were noncompetitive inhibitors and N-arylanthranilic acids were uncompetitive inhibitors.

The rate of cyclization of 2′- and 4′-substituted diphenylamine-2-carboxylic acids in sulfuric acid as a function of the electronic properties of substituents

The kinetic regularities of cyclization of 2′- and 4′-substituted diphenylamine-2-carboxylic acids in sulfuric acid were determined. The rate of cyclization of diphenylamine-2-carboxylic acids is linearly dependent on the nature of substituents in the meta-position relative to the reaction site in accordance with the two-parameter Hammett equation.

Novel synthetic 2-amino-10-(3,5-dimethoxy)benzyl-9(10H)-acridinone derivatives as potent DNA-binding antiproliferative agents

A series of novel 9(10H)-acridinone derivatives with terminal amino substituents at C2 position on the acridinone ring were synthesized and studied for their antiproliferative activity and underlying mechanisms. These compounds demonstrated promising cytotoxicity to leukemia cells CCRF-CEM, displaying IC50 values in the low micromolar range. Structure-activity relationships (SAR) indicated that the compound 6d bearing a pyrrolidine substituent and 8a with a methyl ammonium side chain displayed higher cytotoxicity to CCRF-CEM cells and also solid tumor cells A549, HepG2, and MCF7. Furthermore, the compounds 6d and 8a had strong binding activity to calf thymus DNA (ct DNA), as detected by UV absorption and fluorescence quenching assays, but limited inhibitory activity to human topoisomerase 1 (topo 1). Taken together, this study discovered a series of new synthetic 9(10H)-acridinone derivatives with potent DNA binding and anticancer activity.

Acridone derivatives as labels for fluorescence detection of target materials

Disclosed are new acridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the acridone dyes and use of the labelled materials in biological assays. The acridone derivatives have the following structure:in which Z1 and Z2 represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R2, R3, R4 and R5 are selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C1-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-C6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quatemary ammonium, the group —E—F and the group —(CH2—)nY; R1 is selected from hydrogen, mono- or di-nitro-substituted benzyl, C1-C20 alkyl, aralkyl, the group —E—F and the group —(CH2—)nY; where E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6. The invention also relates to a set of different fluorescent acridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis.

New sulphonamides with acridinic nucleus

Twelve new sulphonamides with acridonic and acridinic nucleus were synthesized, in which the sulphonamidic group appears in positions 1, 2, 3 and 4. We also obtained the corresponding acridanes, but we did not isolate them. We proved that in the case of 2-nitroacridone synthesis, by ring closure of 4-nitrodiphenylamine-2-carboxylic acid, working in the presence of sulphuric acid, sulphonation takes place. To reduce some nitroacridones we used hydrazine hydrate in the presence of Ni from formiate and Ni Raney, a method not yet mentioned in the literature for compounds of this class, and which presents many advantages. We proved that sulphonamides with acridonic nucleus can be transformed into the corresponding acridines, by reduction with Na-amalgam. The studied new substances show a noteworthy activity against microorganisms.

Substituent Effects on the Hydrolysis of Analogues of Nitracrine -1-nitroacridine>

Studies of the hydrolysis of the hypoxia-selective cytotoxic agent 9--1-nitroacridine (nitracrine) and several of its 4-substituted analogues and nitro-positional isomers have been carried out.Examination of the effects of pH and temperature on the hydrolysis of nitracrine itself shows that the reaction is subject to acid catalysis.The value of ΔH(excit.) increases from 46 to 63 kJ mol-1 as the pH falls from 6 to 3, while the value of ΔS(excit.) increases from -195 to -138 J k-1 mol-1.The rate constants for hydrolysis and the acid dissociation constants have been measured at pH 5 and 60 deg C.Both the rate constants of hydrolysis, corrected for the substrate-protonation equilibrium, and the substrate-acid association constants are well fitted by the Ehrenson-Brownlee-Taft dual-substituent-parameter ?R- relationship.The Swain-Unger-Rosenquist-Swain relationship shows weak correlation but the linear free-energy relationships of Hammett and Yukawa-Tsuno are not fitted.The results are discussed in terms of the resonance interactions of the possible intermediates in the hydrolysis pathways.