66073-40-3

Usage

Family

Acridine

Structure

Central acridine molecule with an amino group (NH2) at the 1-position and a carbonyl group (C=O) at the 10-position

Applications

a. Organic synthesis
b. Pharmaceuticals
c. Materials science

Relevance

Unique structure and reactivity make it of interest for researchers studying interactions with biological systems and potential medicinal use

Additional uses

a. Fluorescent probe
b. 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

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

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 academic research and scientific papers

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.

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.

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.

NUCLEOPHILIC SUBSTITUTION OF HYDROGEN ATOM IN 1-NITROACRIDINE DERIVATIVES. PART II. MECHANISM OF 1-NITRO-9-PIPERIDINOACRIDINE REACTION WITH PIPERIDINE. INTRAMOLECULAR TRANSFER OF OXYGEN ATOM FROM THE NITRO GROUP TO ACRIDINE RING

The mechanism of 1-amino-2,4-dipiperidinoacridone formation in reaction of 1-nitro-9-piperidinoacridine with piperidine was investigated.Formation of acridone was proved to be due to non-typical stabilization of Meisenheimer complex.It was found that intramolecular nucleophilic substitution of the acridine ring with the oxygen atom was originated by the 1-nitro group.