13625-57-5Relevant articles and documents
A study on the interaction between p60c-Src receptor tyrosine kinase and arylcarboxylic and arylacetic acid derivatives based on docking modes and in vitro activity
Altuntas, Tunca Gul,Olgen, Sureyya,Nebioglu, Dogu,Akaho, Eiichi
, p. 61 - 65 (2004)
The fundamental role that receptor tyrosine kinases play in cancer and other proliferative diseases has provided the impetus for an extensive effort on the part of both academic and pharmaceutical laboratories to develop highly specific inhibitors. In thi
TiO2-modified MALDI target for in vitro modeling of the oxidative biotransformation of diclofenac
Babakov, Vladimir N.,Bardin, Alexander A.,Gorbunov, Alexander Yu.,Keltsieva, Olga A.,Krasnov, Konstantin A.,Podolskaya, Ekaterina P.
, p. 220 - 222 (2020)
The UV-induced photocatalytic oxidation in the presence of TiO2 nanoparticles (UV/TiO2-PCO) is a more adequate approach than electrochemical oxidation to simulate the oxidative metabolism of diclofenac based on the comparative analysis of oxidation products using high-resolution tandem mass spectrometry. A simple and fast high-throughput technique is proposed for modeling the oxidative metabolism, which involves UV/TiO2-PCO performed directly on a MALDI target and subsequent analysis by matrix-assisted laser desorption/ionization mass spectrometry. The ranges and yields of diclofenac oxidation products obtained by the conventional bulk UV/TiO2-PCO and the proposed on-target version are in excellent agreement.
Preparation of labelled 2-methoxy-3-alkylpyrazines: Synthesis and characterization of deuterated 2-methoxy-3-isopropylyrazine and 2-methoxy-3-isobutylpyrazine
Gerritsma, David A.,Brindle, Ian D.,Jones, Timothy R.B.,Capretta, Alfredo
, p. 243 - 253 (2003)
Efficient synthetic routes for a number of deuterated analogues of 2-methoxy-3-isopropylpyrazines and 2-methoxy-3-isobutylpyrazines have been developed involving the condensation of glyoxal with an α-amino acid amide followed by methylation with iodomethane. In this way [2H3]2-methoxy-3-isopropylpyrazine, 2-methoxy-3-isopropyl-[2H2]pyrazine, [2H3]2-methoxy-3-isopropyl- [2H2]pyrazine, [2H3]2-methoxy-3-isobutylpyrazine; 2-methoxy-3-isobutyl-[2H2]pyrazine and [2H3]2-methoxy-3-isobutyl- [2H2]pyrazine were prepared and characterized by NMR and MS. Copyright
Polymorphism and cocrystal salt formation of 2-((2,6-dichlorophenyl)amino)benzoic acid, harvest of a second form of 2-((2,6-dimethylphenyl)amino)benzoic acid, and isomorphism between the two systems
Guo, Ju,Li, Tonglei,Li, Yuping,Long, Sihui,Parkin, Sean,Yu, Faquan,Zhang, Mingtao,Zhoujin, Yunping
, p. 681 - 690 (2022/01/28)
2-((2,6-Dichlorophenyl)amino)benzoic acid (2-DCABA), a potential non-steroidal anti-inflammatory drug and an analog of 2-((2,6-dimethylphenyl)amino)benzoic acid (HDMPA) was synthesized and its polymorphism was studied to investigate the effect of double Cl-CH3 exchange. Three forms-two polymorphs (I and II) and one cocrystal salt (S)-were obtained through polymorph screening in a variety of solvents, and the elusive single crystals of form II of HDMPA were harvested through melt crystallization. The crystal forms were characterized by single-crystal X-ray diffraction, powder X-ray diffraction (PXRD), DSC, and FT-IR. Isomorphism and isostructurality were observed between the form I of each system. The polymorphism of 2-DCABA seems to stem from the conformational flexibility of the molecule, similar to that of HDMPA. Hirshfeld analysis revealed different intermolecular interactions contributing to the stability of the crystal form I of 2-DCABA and HDMPA-I, despite their structural similarity. This journal is
Thyroid hormone uptake by hepatocytes: Structure-activity relationships of phenylanthranilic acids with inhibitory activity
Chalmers,Scholz,Topliss,Kolliniatis,Munro,Craik,Iskander,Stockigt
, p. 1272 - 1277 (2007/10/02)
The synthesis of a series of mono- and disubstituted N-phenylanthranilic acids is described. Substituents on the phenyl ring include Cl, CN, OH, CF3, Br, I, CH3, OCH3, and OCF2CF2H. These compounds have been tested for their inhibitory effect on triiodothyronine (T3) uptake by H4 hepatocytes. The nonsteroidal antiinflammatory drugs flufenamic acid, mefenamic acid, and meclofenamic acid and the structurally related compounds 2,3- dimethyldiphenylamine and diclofenac were also tested. The most potent compounds were found to be, in order of decreasing activity, meclofenamic acid (2,6-Cl2,3-CH3), flufenamic acid (3-CF3), mefenamic acid (2,3- (CH3)2), and the compounds with 3,5-Cl2 and 3-OCF2CF2H substituents. The least potent compounds had 3-CN and 3-OH substituents. An analysis of quantitative structure-activity relationships (QSAR) for the series of phenylanthranilic acids showed that the inhibition of T3 uptake is highly dependent on the hydrophobicity of the compound. The relationship between uptake inhibition and the calculated octanol-water partition coefficient (clogP) was found to be parabolic, with optimum inhibitory activity found when the clogP of the phenylanthranilic acid was 5.7. It was also found that the 1-carboxylic acid group of the phenylanthranilic acids was not a prerequisite for uptake inhibition to occur, but its removal or alteration resulted in reduced inhibition.
Structure-activity relationships in a series of anti-inflammatory N-arylanthranilic acids
Kaltenbronn,Scherrer,Short,Jones,Beatty,Saka,Winder,Wax,Williamson
, p. 621 - 627 (2007/10/02)
A large series of N-arylanthranilic acids has been prepared. Many of these compounds show high anti-inflammatory activity as measured by the anti-UV-erythema test. From this series have come the clinically useful nonsteroidal anti-inflammatory agents, flufenamic acid (Arlef), mefenamic acid (Ponstel), and the latest and most potent agent, N-(2,6-dichloro-m-tolyl)anthranilic acid (meclofenamic acid, Meclomen = the sodium salt). The structure-activity relationships of this series is discussed and a graphical representation is presented which allows the prediction of activity of new agents.
