PMID: 40027Aug 1, 1979

Conformational analogues of dopamine. Synthesis and pharmacological activity of (E)- and (Z)-2-(3,4-dihydroxyphenyl)cyclopropylamine hydrochlorides

Journal of Medicinal Chemistry
P W ErhardtW G Anderson

Abstract

(E)- and (Z)-(+/-)-2-(3,4-dihydroxyphenyl)cyclopropylamine hydrochlorides were synthesized as part of a program to assess the importance of conformational isomerism with respect to the various peripheral biological actions of dopamine. Although neither of the compounds possessed dopaminergic activity in the canine renal blood-flow model, both agents were weak alpha-adrenergic agonists and exhibited cardiostimulatory properties similar to dopamine. The E isomer was apprxoximately 5 times more potent than the Z isomer in its alpha-adrenergic activity and approximately 15 times as potent in its cardiac effects. Possible reasons for the lack of renal dopaminergic activity exhibited by the E isomer are presented.

References

Apr 1, 1985·Medicinal Research Reviews·C Kaiser, T Jain
Jul 1, 1980·The Journal of Pharmacy and Pharmacology·A S Horn, J R Rodgers
Aug 16, 2012·Medicinal Research Reviews·Mohammed Naseer Ahmed KhanNaoki Miyata
Mar 1, 1994·Medicinal Research Reviews·R R RuffoloJ P Hieble
Jul 1, 1983·Medicinal Research Reviews·J A Bristol, D B Evans
Aug 26, 2006·Journal of Asian Natural Products Research·L-J HuangD-Q Yu
Jun 21, 2017·Chemistry : a European Journal·Akira MizunoSatoshi Shuto

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