Literature

Abstract

The synthesis, resolution, and absolute configuration assignment of 2-methyl-3-(2,4,5-trihydroxphenyl)alanine (6-OH-alpha-Me-Dopa) are reported. Hemodynamic studies in the rat have shown that this structural analogue and potential metabolite of the clinically useful drug (S)-alpha-Me-Dopa possesses weak hypotensive activity which resides in the R enantiomer. LD50 studies in mice have established that 6-OH-alpha-Me-Dopa is over four times more toxic than alpha-Me-Dopa. Chronic exposure to 6-OH-alpha-Me-Dopa leads to renal and hepatic lesions. The case of oxidation of this hydroquinone to the electrophilic quinone species may contribute to its enhanced toxicity compared to alpha-Me-Dopa.

DOI： 10.1021/jm00186a007

Synthetic and preliminary hemodynamic and whole animal toxicity studies on (R,S)-, (R)-, and (S)-2-methyl-3-(2,4,5-trihydroxyphenyl)alanine

Journal of Medicinal Chemistry 1980.0

Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine

Journal of Medicinal Chemistry 1984.0

Synthesis, redox characteristics, and in vitro norepinephrine uptake inhibiting properties of 2-(2-mercapto-4,5-dihydroxyphenyl)ethylamine (6-mercaptodopamine)

Journal of Medicinal Chemistry 1979.0

In Vivo and in Vitro Studies on the Neurotoxic Potential of 6-Hydroxydopamine Analogs

Journal of Medicinal Chemistry 1995.0

Synthesis of 2-(alkylamino)-5,6- and -6,7-dihydroxy-3,4-dihydroquinazolines and evaluation as potential dopamine agonists

Journal of Medicinal Chemistry 1982.0

Synthesis and Pharmacology of 6-Substituted Benztropines: Discovery of Novel Dopamine Uptake Inhibitors Possessing Low Binding Affinity to the Dopamine Transporter