80949-07-1Relevant articles and documents
The synthesis, analysis, stability and biotransformation of N-(3-methylphenyl)-N'-cyanobenzamidine and analogues (author's transl)
Pfeifer,Barnikow,Schulz,Kraft,Fritsche
, p. 757 - 763 (2007/10/02)
The antivirally active N-(3-methylphenyl)-N'-cyanobenzamidine (1) and some of its analogues were synthetized by the reaction of the ethyl ester of N-cyanobenzimidic acid with the corresponding arylamines. The analytical profile of 1 and of some of its analogues, which is needed for stability and biotransformation studies, was established by means of the following techniques: solubility determination, TLC, UV, IR and MS. When 1 is heated with methanolic HCl and NaOH (0.5 mol/l) for 1 h, several hydrolysis products are formed: m-toluidine, benzoic acid, benzoic acid 3-toluidide, N-(3-methylphenyl)benzamidine, N-(3-methylphenyl)-N'-carboxamidobenzamidine, benzoylurea, However, 1 is fairly stable under physiological conditions so biotransformation studies are not affected. After oral application of 1 to rats, the 3-hydroxymethyl and the 3-methyl-5-hydroxy compound as well as its glucuronide and sulphate conjugate were detected in the urine. The faeces contained considerable amounts of unchanged 1 (incomplete absorption).
