10311-56-5Relevant academic research and scientific papers
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.
Preparation of Ortho-Substituted Benzoic Acids by the Copper(II)-Catalyzed Reaction of Diphenyliodonium-2-carboxylate with Anilines and Other Nucleophiles
Scherrer, Robert A.,Beatty, Helga R.
, p. 2127 - 2131 (2007/10/02)
Diphenyliodonium-2-carboxylate (DPIC) reacts readily in copper ion catalyzed condensations with a variety of nucleophiles to give ortho-substituted benzoic acids.These reactions occur at temperatures (80-100 deg C) below those at which benzyne formation and other side reactions become important.The nature of the Cu(II) catalysis appears to be different from the more common Cu(I) catalysis of diaryliodonium reactions in that high specificity in the displacement reaction is retained.Products obtained directly from DPIC condensations include N-anthranilic acid (5b), N-methyl-N-phenylanthranilic acid (5c), N-mesyl-N-(2,3-dimethylphenyl)anthranilic acid (5d), N-(3-chloro-2-methylphenyl)-N-tosylanthranilic acid (5e), and o-(2,3-dimethylphenoxy)benzoic acid (5f).Compound 5d has been cyclized to N-(2,3-dimethylphenyl)-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide (6).
