Mercapto heterocyclic carboxylic acids, analogues of 3-mercaptopicolinic acid.
3-Mercaptopicolinic acid (3-MPA), a potent hypoglycemic agent in fasted rats, provided the impetus for substituting this compound with a 5-mercapto group (1), a 6-carboxyl group (2), and a 5-mercapto and 6-carboxyl group (3) and for replacing the pyridine ring with other heterocycles: quinoline (4), thiazole (5), pyrazine (6), isoquinoline (7), and indole (8). The methyl sulfoxide (9) and sulfone (10) of 3-MPA were also prepared. The new compounds 1-10, with the exception of 8, did not lower blood glucose levels in 48-h fasted rats. 8 was toxic at doses which were hypoglycemic.
D000818:Animals; D007004:Hypoglycemic Agents / Q000138:chemical synthesis; D008297:Male; D008722:Methods; D010848:Picolinic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
D007004:Hypoglycemic Agents; D010848:Picolinic Acids; D013438:Sulfhydryl Compounds; C008363:3-mercaptopicolinic acid