84954-91-6

Upstream product

• 16463-38-0 potassium 2-chlorobenzoate 
• 95-76-1 m,p-dichloroaniline 
• 16497-87-3 potassium o-bromobenzoate 
• 118-91-2 ortho-chlorobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 

Downstream Products

• 116631-92-6 3,4-dichloro-N-phenylaniline 

Relevant academic research and scientific papers

Thyroid hormone uptake by hepatocytes: Structure-activity relationships of phenylanthranilic acids with inhibitory activity

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.

Use of amino-substituted benzoic acids as remedies for diarrhea, and medicaments based on these compounds

A description is given of the use of amino-substituted benzoic acid derivatives of the formula I STR1 in which R1 and R2 denote hydrogen, (cyclo)alkyl, unsubstituted or substituted phenyl or naphthyl, or R1 and R2 together denote a chain --(CH2)m -- with m=3 to 6, or together denote a chain --(CH=CH)n -- with n equal to 2 or 3; R3 denotes hydrogen, halogen or alkyl; R4 denotes hydrogen or NO2 ; R5 denotes hydrogen or a radical which can be eliminated under physiological conditions; for the preparation of a remedy for diarrhea.

Structure-activity relationships in a series of anti-inflammatory N-arylanthranilic acids

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.