66073-40-3

Basic information

• Product Name: 1-amino-10H-acridin-9-one
• Synonyms: 1-amino-10H-acridin-9-one
• CAS NO: 66073-40-3
• Molecular Formula: C13H10N2O
• Molecular Weight: 210.2313
• Mol File: 66073-40-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 422.7°Cat760mmHg
• Flash Point: 209.4°C
• Appearance: /
• Density: 1.306g/cm³
• Vapor Pressure: 2.36E-07mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 1-amino-10H-acridin-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-10H-acridin-9-one(66073-40-3)
• EPA Substance Registry System: 1-amino-10H-acridin-9-one(66073-40-3)

Safety Data

• Hazardous Substances Data: 66073-40-3(Hazardous Substances Data)

Usage

General Description

1-Amino-10H-acridin-9-one is a chemical compound with the molecular formula C13H10N2O. It belongs to the acridine family and consists of a central acridine molecule with an amino group (NH2) attached at the 1-position and a carbonyl group (C=O) attached at the 10-position. 1-amino-10H-acridin-9-one has potential applications in organic synthesis, pharmaceuticals, and materials science due to its unique structure and reactivity. Its properties and behavior are of interest for researchers studying the interactions of acridine derivatives with biological systems and their potential for medicinal use. Additionally, 1-Amino-10H-acridin-9-one may also be used as a fluorescent probe and as a precursor in the synthesis of various functional materials.

InChI:InChI=1/C13H10N2O/c14-9-5-3-7-11-12(9)13(16)8-4-1-2-6-10(8)15-11/h1-7H,14H2,(H,15,16)

Upstream product

• 35118-96-8 2-acetylamino-6-anilino-benzoic acid 
• 857616-10-5 1-amino-9-oxo-9,10-dihydro-acridine-4-carboxylic acid 
• 25293-29-2 N-(3-amino-phenyl)-anthranilic acid 
• 4533-39-5 nitracrine 
• 3483-12-3 diothiothreitol 
• 62-53-3 aniline 
• 19407-42-2 2-(acetylamino)-6-chlorobenzoic acid 
• 118-92-3 anthranilic acid 
• 71835-14-8 2-((2-carboxyphenyl)amino)-4-nitrobenzoic acid 
• 71507-04-5 1-nitro-9-oxo-9,10-dihydroacridine-4-carboxylic acid 
• 27693-70-5 N-(3-nitrophenyl)anthranilic acid 
• 99-60-5 2-chloro-4-nitrobenzoic acid 
• 40239-75-6 1-nitro-9-acridanone 

Downstream Products

• 578-06-3 acridin-1-ylamine 
• 148902-85-6 1-(acetylamino)acridone 
• 121083-77-0 1-amino (10H)-acridine-9-thione 
• 676456-12-5 1-(p-aminobenzenesulphonylamino)acridone 

Relevant articles and documents

Products of metabolic activation of the antitumor drug ledakrin (Nitracrine) in vitro

The aim of this work was to characterize the products of metabolic activation of the antitumor drug ledakrin (Nitracrine) in model metabolic systems, where formation of drug - DNA adducts was previously discovered. The metabolic products obtained in different biological systems were compared with those obtained in experiments where chemical reducing agents were applied. Therefore, activation products were obtained in the presence of the microsomal fraction of rat liver and in the experiments with the reducing agents dithiothreitol, hydrazine hydrate, and SnCl2. Furthermore, transformations of the drug with oxidoreductase enzymes DTdiaphorase and xanthine oxidase were observed. The ledakrin transformation products were separated and analyzed by HPLC with diode array detection. Structural studies of the products were performed by means of ESI-MS and NMR. Proton, carbon, and nitrogen assignments were made based upon DQF-COSY, ROESY, TOCSY, HSQC, and HMBC experiments. It was demonstrated during the reduction of ledakrin that a key metabolite, a compound with an additional five-membered ring attached to positions 1 and 9 of the acridine core and with the retained 9-aminoalkyl side chain, was formed in all the systems that were studied. It was determined that the reactive nitrogen atoms of this additional ring underwent further transformations resulting in the formation of a six-membered ring produced by the addition of a carbon atom to the dihydropyrazoloacridine ring. Furthermore, it was observed that positions 2 and 4 of ledakrin's acridine ring are susceptible to nucleophilic substitution as revealed by the studies with dithiothreitol. Additionally, although most products from the reduction of ledakrin were-extremely unstable, 1-aminoacridinone, produced enzymatically and with dithiothreitol, exhibited persistent stability under the studied conditions.

Research on tumour inhibiting compounds. Part LXIX. Reactions of 1-nitroacridines and 1-nitro-9-acridones with hydrogen sulfide

Reaction of 1-nitro-9-(3-N,N-dimethylaminopropylamino)acridine with hydrogen sulfide in pyridine affording unstable 1,9-dithiolacridine, 1-amino-4-thiol-9-thioacridone, 1-amino-2,4-dithiol-9-thioacridone and 1-hydroxylamino-9-thioacridone has been described.Unstable products were identified as 1,9-dithiolacridine, S-methyl derivatives of aminothioacridone and 1-acetylamino-9-thioacridone, respectively.Moreover, reactions of 1-nitro-9-acridones with hydrogen sulfide affording 1-amino- and 1-hydroxylamino-9-acridones have been described.