42946-36-1Relevant academic research and scientific papers
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
Pelevin,Markovich,Nazarov,Galan,Kudryavtseva,Brylev
, p. 590 - 592 (2011)
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.
Synthesis, cytotoxicity evaluation, and molecular modeling studies of 2,N10-substituted acridones as DNA-intercalating agents
Chimnoi, Nitirat,Eurtivong, Chatchakorn,Jumpathong, Watthanachai,Khunnawutmanotham, Nisachon,Techasakul, Supanna
, p. 410 - 425 (2020/03/23)
Acridine-based compounds possess anticancer activities by intercalating to DNA. Although they have chemotherapeutic potential, acridine-based compounds are not used to treat cancer. In this study, 2,N10-acridone derivatives are designed and synthesized based on acridone, a ketone derivative of acridine. Herein, acridone is functionalized with alkyl side chains containing terminal nitrogen-based moieties at the N10-position and substituted at the C2-position. The products are evaluated for in vitro cytotoxicity against four cancer cell lines: Molt-3, HepG2, A549, and HuCCA-1. The derivative bearing two butyl piperidine side chains at the C2- and N10-positions is the most active, with IC50 values ranging from 2.96 to 9.46 μM. Molecular modeling studies supported the binding of the derivatives to DNA by intercalation, thereby confirming the observed cytotoxic effects.
Nitric oxide releasing acridone carboxamide derivatives as reverters of doxorubicin resistance in MCF7/Dx cancer cells
Rajendra Prasad,Deepak Reddy,Kathmann, Ietje,Amareswararao,Peters
, p. 51 - 58 (2015/12/17)
A series of nitric oxide donating acridone derivatives are synthesized and evaluated for in vitro cytotoxic activity against different sensitive and resistant cancer cell lines MCF7/Wt, MCF7/Mr (BCRP overexpression) and MCF7/Dx (P-gp expression). The resu
Developing bivalent ligands to target CUG triplet repeats, the causative agent of myotonic dystrophy type 1
Jahromi, Amin Haghighat,Fu, Yuan,Miller, Kali A.,Nguyen, Lien,Luu, Long M.,Baranger, Anne M.,Zimmerman, Steven C.
supporting information, p. 9471 - 9481 (2014/01/06)
An expanded CUG repeat transcript (CUGexp) is the causative agent of myotonic dystrophy type 1 (DM1) by sequestering muscleblind-like 1 protein (MBNL1), a regulator of alternative splicing. On the basis of a ligand (1) that was previously reported to be active in an in vitro assay, we present the synthesis of a small library containing 10 dimeric ligands (4-13) that differ in length, composition, and attachment point of the linking chain. The oligoamino linkers gave a greater gain in affinity for CUG RNA and were more effective when compared to oligoether linkers. The most potent in vitro ligand (9) was shown to be aqueous-soluble and both cell- and nucleus-permeable, displaying almost complete dispersion of MBNL1 ribonuclear foci in a DM1 cell model. Direct evidence for the bioactivity of 9 was observed in its ability to disperse ribonuclear foci in individual live DM1 model cells using time-lapse confocal fluorescence microscopy.
Kinetic parameters of the intramolecular condensation of diphenylamine-2-carboxylic acid under microwave radiation
Markovich,Kudryavtseva,Brylev,Markovich,Koroleva
experimental part, p. 149 - 152 (2012/06/04)
The cyclization of diphenylamine-2-carboxylic acid under microwave radiation was investigated. The kinetic parameters of the processes were measured. The use of microwave radiation was found to reduce the reaction duration and to increase the target produ
Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity
Goodell, John R.,Madhok, Avni A.,Hiasa, Hiroshi,Ferguson, David M.
, p. 5467 - 5480 (2007/10/03)
The discovery of new non-nucleoside antiviral compounds is of significant and growing interest for treating herpes virus infections due to the emergence of nucleoside-resistant strains. Using a whole cell virus-induced cytopathogenic assay, we tested a se
Synthesis and photophysics of acridine derivatives
Szymanska,Wiczk,Lankiewicz
, p. 801 - 808 (2007/10/03)
Highly fluorescent acridine derivatives were prepared by a multistep synthesis starting from 2-chlorobenzoic acid and the appropriate (aminophenyl)alkanoic acid by means of a modified Ullmann-Jourdan reaction followed by a cyclodehydration step, and by am
Synthesis and structure-activity relationships of anti-inflammatory 9,10-dihydro-9-oxo-2-acridine-alkanoic acids and 4-(2-carboxyphenyl)aminobenzenealkanoic acids
Taraporewala,Kauffman
, p. 173 - 178 (2007/10/02)
Eighteen test compounds, in three chemical series, were prepared as potential anti-inflammatory agents and evaluated by the rat hindpaw carrageenan-induced edema assay. The compounds, isosteric with known anti-inflammatory and antiallergic cyclo-oxygenase
Acridone-dicarboxylic acids
-
, (2008/06/13)
Certain acridone and xanthone compounds, each of which is 2-substituted by a carboxyl group or a salt, ester or optionally substituted amide thereof and each of which is optionally substituted in the 5-, 6-, 7- or 8-position, by a second carboxyl group, s
