Mercapto heterocyclic carboxylic acids, analogs 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),...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1977-04, Vol.20 (4), p.572-576
Main Authors: Blank, Benjamin, DiTullio, Nicholas W, Owings, Franklin F, Deviney, Linda, Miao, Clara K, Saunders, Harry L
Format: Article
Language:English
Subjects:
Animals
Hypoglycemic Agents - chemical synthesis
Male
Methods
Picolinic Acids - chemical synthesis
Picolinic Acids - pharmacology
Rats
Structure-Activity Relationship
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - pharmacology
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00214a023