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1,2-Dihydro-2-oxo-6-(2,2-dimethylpropyl)-3-pyridinecarboxylic Acid, Analogues, and Derivatives. A New Class of Oral Hypoglycemic Agents

1,2-Dihydro-2-oxo-6-(2,2-dimethylpropyl)-3-pyridinecarboxylic Acid, Analogues, and Derivatives. A New Class of Oral Hypoglycemic Agents

G A Youngdale, T F Oglia

J Med Chem. 1985 Dec;28(12):1790-6.

PMID: 4068003

Abstract:

1,2-Dihydro-2-oxo-6-(2-methylpropyl)-3-pyridinecarboxylic acid was found to be a hypoglycemic agent but not to have the undesirable mechanism of action possessed by nicotinic acid. A series of 1,2-dihydro-2-oxo-3-pyridinecarboxylic acids with a substituent primarily at the 6-position was prepared by hydrolysis of the corresponding nitriles. The nitriles were prepared by reaction of the sodium enolate of the appropriate 3-substituted 3-oxopropionaldehyde with cyanoacetamide. The sodium enolates were synthesized from ethyl formate and the appropriate ketone and sodium or sodium hydride. The active 1,2-dihydro-2-oxo-3-pyridinecarboxylic acids, listed in order of decreasing hypoglycemic potency, had the following substituents: 6-(2,2-dimethylpropyl), 6-(2,2-dimethylbutyl), 6-(1,1-dimethylethyl), 6-(2-methylpropyl), 6-(1,1-dimethylpropyl), 1-methyl-6-(2-methylpropyl), 6-hydrogen. The inactive compounds were those with 6-methyl, 6-(1-methylethyl), 6-pentyl, 4-(2,2-dimethylpropyl), 6-(3-methylbutyl), 6-(1,1-dimethylheptyl), 6-(2,2-dimethyloctyl), 6-(1-cyclobutylmethyl), and 1-methyl-6-(2,2- dimethylpropyl) substituents. The corresponding alcohol, aldehyde, tetrazole, sodium salt, and ethyl ester of the most potent acid were also active compounds. The corresponding amide, decarboxyl compound, and 2-deoxo compound were inactive.

Chemicals Related in the Paper:

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LS7931257	1-(3-Methylbutyl)-1H-pyrazole-4-boronic acid			Price

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