31327-97-6

Usage

Synthesis Reference(s)

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

Upstream product

• 24782-64-7 9-Oxoacridan-4-carboxylic 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 academic research and scientific papers

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.

Cell-specific and nuclear targeting with [M(CO)3]+ (M = 99mTc, Re)-based complexes conjugated to acridine orange and bombesin

Receptor-specific nuclear targeting requires trifunctional metal complexes. We have synthesized [M(L2-pept)(L1-acr)(CO)3] (pept = peptide: acr = acridine-based agent) in which the fac-[M(CO) 3]+ moicty (1st function, M = 99mTc. Re) couples an acridine-based nuclear-targeting agent (2nd function. L 1-acr) and the specific cell-receptor-binding peptide bombesin (3rd function, L2-pept). The metalmediated coupling is based on the mixed ligand [2+1] principle. The nuclear targeting agents have been derivatised with an isocyanide group for monodentate (L1) and bombesin (BBN) with a bidentate ligand (L2) for complexation to fac-[M(CO)3]+. For nuclear uptake studies, the model complexes [Re(L2)(L 1-acr)(CO)3] (L2 = pyridine-2-carhoxylic acid and pyridine2.4-dicarhoxylic acid) were synthesized and structurally characterized. We selected acridine derivatives as nucleartargeting agents, because they are very good nucleus-staining agents and exhibit strong fluorescence. Despite the bulky metal complexes attached to acridine. all [Re(L2)(L1-acr)(CO)3] showed high accumulation in the nuclei of PC3 and B16F1 cells, as evidenced by fluorescence microscopy. For radio-pharmaceutical purposes, the 99mTc analogues have been prepared and radioactivity distribution confirmed the fluorescence results. Coupling of BBN to L2 gave the receptor-selective complexes [M(L 2-BBN)(L1-acr)(CO)3]. Whereas no internalization was found with B16F1 cells, fluorescence microscopy on PC3 cells bearing the BBN receptor showed high and rapid uptake by receptor-mediated endocytosis into the cytoplasm, but not into the nucleus.

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.

Process for the preparation of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide

PCT No. PCT/GB97/02884 Sec. 371 Date Jun. 18, 1999 Sec. 102(e) Date Jun. 18, 1999 PCT Filed Oct. 17, 1997 PCT Pub. No. WO98/17649 PCT Pub. Date Apr. 30, 1998A process for producing an acridine carboxamide of formula (I): wherein each of R1, R2, R5 and R6,

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.

A new synthesis of substituted acridine-4-carboxylic acids and the anticancer drug N-[2-dimethylamino)ethyl]acridine-4-carboxamide (DACA)

A new synthesis of substituted acridine-4-carboxylic acids 2 from methyl 2-[N-(2-carboxyphenyl)amino]benzoates (4) is reported, via NaBH4 reduction of the corresponding imidazolides (5), oxidation of the resulting alcohols 6 to aldehyde 7, and cyclisation of these with trifluoroacetic acid to the methyl acridine-4-carboxylates (8), followed by base hydrolysis. Direct amidation of 8a provides a new route to the clinical anticancer drug DACA (3) which avoids use of the irritant acid 2a.

Structure-activity relationships for acridine-substituted analogues of the mixed topoisomerase I/II inhibitor N-[2-(dimethylamino)ethyl] acridine- 4-carboxamide

The mixed topoisomerase I/II inhibitor N-[2- (dimethylamino)ethyl]acridine-4-carboxamide (DACA) is currently in clinical trial as an anticancer drug. A series of acridine-substituted analogues were prepared, using a new synthetic route to substituted acri

Potential Antitumor Agents. 50. In Vivo Solid-Tumor Activity of Derivatives of N-acridine-4-carboxamide

The synthesis, physicochemical properties, and antitumor activity of a series of N-acridine-4-carboxamides are reported.The compounds bind to DNA by intercalation, but exist under physiological conditions as monocations due to the w

Acridinecarboxamide compounds

4-Carboxamidoacridine compounds represented by the general formula (I), STR1 where R1 represents H, CH3 or NHR3, where R3 is H, COCH3, SO2 CH3, COPh, SO2 Ph or lower alkyl optionally substituted with hydroxyl and/or amino functions; R2 represents H or up to two of the groups CH3, OCH3, halogen, CF3, NO2, NH2, NHCOCH3, and NHCOOCH3 placed at positions 1-3 or 5-8; Y represents C(NH)NH2, NHC(NH)NH2, or NR4 R5, where each of R4 and R5 is H or lower alkyl optionally substituted with hydroxyl and/or amino functions; and x is from 2 to 6, and the acid addition salts thereof, possess antibacterial and antitumor properties.