Mansuy, Daniel published the artcileMetabolic hydroxylation of the thiophene ring: isolation of 5-hydroxytienilic acid as the major urinary metabolite of tienilic acid in man and rat, Application In Synthesis of 40180-04-9, the main research area is tienilate metabolism.
The metabolism of tienilic acid (I) [40180-04-9], a drug containing a thiophene ring, was reinvestigated with man, rat and dog. The major urinary metabolite in man and rat was isolated and completely characterized by comparison with a synthetic compound This metabolite derives from the hydroxylation of the thiophene ring of tienilic acid in position 5. Its isomers, 3- [90966-20-4] and 4-hydroxytienilic acid [90966-19-1], were synthesized but could be detected neither in man nor in rat urine. Because of its particular behavior toward electrophiles, 5-hydroxytienilic acid [90966-18-0] reacted with diazomethane with the formation of a complex mixture of methylated products. This made difficult its measurement by a previously described GLC technique, after acidic extraction and methylation by diazomethane. A new very simple assay using HPLC and direct injection of urine is described in this paper. This assay led to a very precise and reproducible determination of tienilic acid and its hydroxylated metabolite in urine. Up to 50% of tienilic acid is excreted in man or rat urine as 5-hydroxytienilic acid whereas this metabolite does not appear in dog urine. These data describe the first example of metabolic hydroxylation of the thiophene ring.
Biochemical Pharmacology published new progress about tienilate metabolism. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Application In Synthesis of 40180-04-9.
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem