Clara K. Miao

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.

1,2-Diacyl-sn-glycerols and 2,3-diacyl-sn-glycerols.

Abstract This is an example of a facile synthesis of both enantiomeric 1,2-diglycerides from one common intermediate which is applicable to polyunsaturated groups esterified to glycerol.

Metabolism of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline, a phenylethanolamine N-methyltransferase inhibitor. II. Species difference in metabolism and synthesis of its metabolites

1. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (DCTQ), a potent reversible inhibitor of phenylethanolamine N-methyltransferase, was well absorbed, readily metabolized and excreted mainly in urine. 2. Its pathways of metabolism in rats and dogs were markedly different. In the dog, N-methylation was followed by N-oxidation to give the corresponding N-methyl-N-oxide as the final metabolic product. This was not observed in the rat. 3. In the rat, major pathways are aromatization of DCTQ to the corresponding isoquinoline and subsequent hydroxylation in the hetero ring to all three possible isomeric hydroxy-isoquinolines. 4. Authentic metabolites were synthesized for comparison with metabolites isolated from urine.