Syntheses and in vitro evaluation of 4-(2-aminoethyl)-2(3H)-indolones and related compounds as peripheral prejunctional dopamine receptor agonists
Citations Over TimeTop 11% of 1986 papers
Abstract
A series of (beta-aminoethyl)indolones and related compounds was synthesized and evaluated in vitro as peripheral prejunctional dopaminergic agonists in the field-stimulated isolated perfused rabbit ear artery. 4-[2-(Di-n-propylamino)ethyl]-7-hydroxy-2(3H)-indolone was the most potent compound (ED50 = 2 +/- 0.3 nM) tested, while the related secondary amine 24 and the des-OH derivatives 28 and 34 were only slightly less potent. 4-Methoxybenzeneethanamine and 2-methyl-3-nitrophenylacetic acid were employed as starting materials for for the synthesis of the 4-(beta-aminoethyl)indolones. The ring-opened 3-acylamino analogues 46 and 47 were prepared via nitration of the phenethylamine 43 derived from 4-methoxyphenylacetic acid. The inactive isomeric indolones 38, 39, and 41 were derived from 4-nitrobenzeneethanamine and from indolone-6-acetic acid.
Related Papers
- → Distribution and levels of dopamine and its metabolites in brains of reproductive workers in honeybees(2001)87 cited
- → Role of oxidative changes in the degeneration of dopamine terminals after injection of neurotoxic levels of dopamine(2000)116 cited
- → Dopamine receptors in C. elegans(2004)51 cited
- → Caste differences in dopamine-related substances and dopamine supply in the brains of honeybees (Apis mellifera L.)(2012)26 cited
- → LSD labels a novel dopamine receptor in molluscan nervous system(1978)34 cited