N-Arylanthranilic acid

Boltze, K. H. and Kreisfeld, H. [On the chemistry of etofenamate, a novel anti-inflammatory agent from the series of N-arylanthranilic acid derivatives (author s transl)], Arzneim.-Forsch./Drug Res. 

N-Arylanthranilie Acids (2). In equations 21 and 22 it can be seen tnat the N-arylanthranilic acids are similar to phenols (eq 12, 13) in the effect of pKa on activity. The more acidic the anthranilic acid, the more potent it will be as an uncoupler for any given log P. In contrast, binding to bovine serum albumin for some of the same compounds is satisfied by an equation in log D alone (eq 23). The pKa terms in eq 21 and 22 may not be significant enough to make anything of the difference in magnitude of the pKj, coefficients between heart and liver mitochondria, but this is a potential tool for this type of compar-i son. 

Bajaj, S., Sambi, S.S. and Madan, A.K. (2005) Prediction of anti-inflammatory activity of N-arylanthranilic acids computational approach using refined Zagreb indices. Croat. Chan. Acta, 78, 165-174. 

Duffy, J.C., Dearden, J.C. and Rostron, C. (1996) A QSAR study of antiinflammatory N-arylanthranilic acids. J. Pharm. Pharmacol., 48, 883-886. 

The structural analogues of N-arylanthranilic acid opened an altogether new horizon of antipyretic, analgesic and anti-inflammatoiy compounds which have recently gained recognition in the therapeutic armamentarium. A few compounds belonging to this category are discussed here. 

Structural analogues of N-arylanthranilic acid yielded some potent antipyretic, analgesic and anti-inflammatory compounds . Justify the statement with two important examples along with their synthesis. 

The pKa values of the N-arylanthranilic acids (4.0-4.2) resemble those of the arylalkanoic acids thus, it is not surprising that they are strongly bound to plasma proteins and that interactions with other highly protein bound drugs are very probable. The most common interactions reported are those of mefenamic acid and meclofenamic acid with oral anticoagulants. Concurrent administration of aspirin results in a reduction of plasma levels of meclofenamic acid. 

A few reactions of aryl chlorides catalyzed by ligated copper complexes have been reported. The reaction of phenyl chloride with diphenylamine to form triarylamines catalyzed by the complexes of CuL(PPh3)Br in which L is 1,10-phenanthroline, neocuproine, or 2,2 -bipyridine occurred in about 50% yield. The favorable effect of potentially coordinating ortho substituents on the rates of Ullmann reactions has been exploited to couple o-chlorobenzoic acids with anilines to form N-arylanthranilic acids in aqueous or DMF solutions in the presence of pyridine. ... 

The reagent does not replace nitrogen atoms, and N-alkyl or N-aryl anthranilic acids yield 2,l-benzisothiazoline-3-thiones (94) on heating with phosphorus pentasulfide in xylene. Curiously, when alkyl iV-arylanthranilates are treated in the same way, only a very small proportion—less than 10%— of 94 is obtained. The major product (80%) is the cyclic phosphorus-containing compound (95), the identification of which gives some clue about the structures of possible intermediates.122... 

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