We report unexpected results in an investigation of cyclic analogues of dopamine and norepinephrine possessing the structures 1-(aminomethyl)-5,6-dihydroxy-1,2,3,4-tetrahydronaphthalene (3) and 1-(aminomethyl)-5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthalenol (7). N-Isopropyl substitution of these compounds, providing 4 and 8, brings about the total disappearance of their stimulant activity on beta-adrenergic receptors. On the basis of current knowledge about the structure-activity relationship of adrenergic drugs, it is difficult to provide an explanation for these results; however a tentative rationalization based on conformational considerations is suggested.

An anomalous effect of N-isopropyl substitution in determining beta-adrenergic activity

LAPUCCI, ANNALINA;MANERA, CLEMENTINA;NENCETTI, SUSANNA;BRESCHI, MARIA CRISTINA;LUCACCHINI, ANTONIO;MARTINI, CLAUDIA;
1988-01-01

Abstract

We report unexpected results in an investigation of cyclic analogues of dopamine and norepinephrine possessing the structures 1-(aminomethyl)-5,6-dihydroxy-1,2,3,4-tetrahydronaphthalene (3) and 1-(aminomethyl)-5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthalenol (7). N-Isopropyl substitution of these compounds, providing 4 and 8, brings about the total disappearance of their stimulant activity on beta-adrenergic receptors. On the basis of current knowledge about the structure-activity relationship of adrenergic drugs, it is difficult to provide an explanation for these results; however a tentative rationalization based on conformational considerations is suggested.
1988
B., Macchia; A., Balsamo; Lapucci, Annalina; F., Macchia; Manera, Clementina; Nencetti, Susanna; Breschi, MARIA CRISTINA; Lucacchini, Antonio; Martini, Claudia; E., Martinotti
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/197898
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