C (2)-Methylation abolishes DA1 dopamine agonist activity of 2-amino-6, 7-dihydroxy-1, 2, 3, 4-tetrahydronaphthalene (6, 7-ADTN): steric intolerance by the receptor

…, JN Jacob, AJ Hoffman, JD Kohli, D Glock

Index: Nichols, David E.; Jacob, James N.; Hoffman, Andrew J.; Kohli, Jai D.; Glock, Dana Journal of Medicinal Chemistry, 1984 , vol. 27, # 12 p. 1701 - 1705

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Citation Number: 9

Abstract

The synthesis of 2-amino-2-methyl-6, 7-dihydroxy-1, 2, 3, 4-tetrahydronaphthalene is reported. This compound did not produce vasodilation in the dog renal artery and was inactive as a DA,-type dopamine agonist. This is in contrast to the 2-nonmethylated homologue 6, 7-ADTN, which is a potent DA1 agonist. High-field lH NMR studies of the 0, O- dimethyl ethers for both compounds as their free bases in chloroform-d revealed that the 2 ...