[The synthesis, analysis, stability and biotransformation of N-(3-methylphenyl)-N'-cyanobenzamidine and analogues (author's transl)].
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).
D000578:Amidines / Q000138:chemical synthesis*; D000818:Animals; D000998:Antiviral Agents / Q000032:analysis / Q000138:chemical synthesis* / Q000378:metabolism; D001550:Benzamidines / Q000032:analysis / Q000138:chemical synthesis* / Q000378:metabolism; D001711:Biotransformation; D002855:Chromatography, Thin Layer; D004355:Drug Stability; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D012995:Solubility
D000578:Amidines; D000998:Antiviral Agents; D001550:Benzamidines; C033361:N-(3-methylphenyl)-N'-cyanobenzamidine
Synthese, Analytik, Stabilität und Biotransformation von N-(3-Methylphenyl)-N'-cyanbenzamidin und Analoga.