31327-97-6

Basic information

• Product Name: Acridine-4-carboxylic acid
• Synonyms: Acridine-4-carboxylic acid;4-Acridinecarboxylic acid
• CAS NO: 31327-97-6
• Molecular Formula: C₁₄H₉NO₂
• Molecular Weight: 223.23
• Mol File: 31327-97-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 202-204 °C(Solv: acetone (67-64-1))
• Boiling Point: 480.4±18.0 °C(Predicted)
• Appearance: /
• Density: 1.366±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.49±0.30(Predicted)
• CAS DataBase Reference: Acridine-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Acridine-4-carboxylic acid(31327-97-6)
• EPA Substance Registry System: Acridine-4-carboxylic acid(31327-97-6)

Safety Data

• Hazardous Substances Data: 31327-97-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 38, p. 699, 1997 DOI: 10.1016/S0040-4039(96)02396-9

Upstream product

• 27574-29-4 acridine-4,9-dicarboxylic acid 
• 188054-37-7 N-(2-Hydroxymethylphenyl)anthranilsaeuremethylester 
• 188054-38-8 N-(2-Formylphenyl)anthranilsaeuremethylester 
• 100038-81-1 methyl 2-benzoate 
• 190845-20-6 2-[N-(2-carboxyphenyl)amino]phenylpyruvic acid 
• 3486-31-5 isatin sodium salt 
• 16463-39-1 2-iodobenzoic acid potassium salt 
• 253120-47-7 2-amino-3-(methoxycarbonyl)benzoic acid 
• 253120-48-8 methyl 2-amino-3-(hydroxymethyl)benzoate 
• 253120-49-9 methyl 2-amino-3-formylbenzoate 
• 103030-10-0 methyl 7-isatincarboxylate 
• 25128-35-2 isatin-7-carboxylic acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 579-92-0 Vanadox 

Downstream Products

• 106626-64-6 Acridine-4-carboxylic acid [2-(2-hydroxy-ethylamino)-ethyl]-amide 
• 106626-63-5 acridine-4-carboxylic acid (2-aminoethyl)amide 
• 89459-25-6 N-[2-(dimethylamino)ethyl]acridine-4-carboxamide 
• 106626-57-7 Acridine-4-carboxylic acid (3-dimethylamino-propyl)-amide 
• 106626-61-3 N-(2-diethylaminoethyl)-acridine-4-carboxamide 
• 106626-58-8 N-(2-(dimethylamino)butyl)acridine-4-carboxamide 
• 106626-59-9 Acridine-4-carboxylic acid (5-dimethylamino-pentyl)-amide 
• 106626-60-2 N-(2-(dimethylamino)hexyl)acridine-4-carboxamide 
• 106626-62-4 N-(2-(methylamino)ethyl)acridine-4-carboxamide 
• 745014-27-1 (2S)-N-{4-[2'-(4-acridinylcarboxamido)-ethyl]-oxy-5-methoxy-2-nitrobenzo-yl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 745014-33-9 (2S)-N-{4-[2'-(4-acridinylcarboxamido)-propyl]-oxy-5-methoxy-2-nitroben-zoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 745014-28-2 (2S)-N-{4-[2'-(4-acridinylcarboxamido)-ethyl]-oxy-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 745014-34-0 (2S)-N-{4-[3'-(4-acridi-nylcarboxamido)-propyl]-oxy-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 142038-90-2 Acridine-4-carboxylic acid [6-(2-amino-ethylamino)-hexyl]-amide 

Relevant articles and documents

Design, synthesis, and DNA sequence selectivity of formaldehyde-mediated DNA-adducts of the novel N-(4-aminobutyl) acridine-4-carboxamide

A novel derivative of the anti-tumor agent N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) was prepared by reduction of 9-oxoacridan-4-carboxylic acid to acridine-4-carboxylic acid with subsequent conversion to N-(4-aminobutyl)acridine-4-carboxamide (C4-DACA). Molecular modeling studies suggested that a DACA analogue comprising a side chain length of four carbons was optimal to form formaldehyde-mediated drug-DNA adducts via the minor groove. An in vitro transcription assay revealed that formaldehyde-mediated C4-DACA-DNA adducts selectively formed at CpG and CpA dinucleotide sequences, which is strikingly similar to that of formaldehyde-activated anthracenediones such as pixantrone.

Synthesis of C8-linked pyrrolo[2,1-c][1,4]benzodiazepine-acridone/acridine hybrids as potential DNA-binding agents

Pyrrolobenzodiazepine hybrids linked to acridone/acridine ring systems at C8-position have been designed and prepared that exhibit significant DNA-binding affinity, and a representative compound shows promising in vitro anticancer activity.

A preparation of methyl 2-amino-3-formylbenzoate and its use in Friedlander synthesis

The title compound has been prepared in four steps from methyl isatin-7- carboxylate. Condensations with 1-indanone and analogs gave 11H-indeno[1,2- b]quinoline-6-carboxylic acids, and with cyclohexanones gave acridine-4- carboxylic acids.