Conformationally defined adrenergic agents. 9. Binding requirements of phenolic phenylethylamines in the benzonorbornene skeleton at the active site of …

GL Grunewald, WJ Bartlett, TJ Reitz…

Index: Grunewald, Gary L.; Arrington, Hugh S.; Bartlett, William J.; Reitz, Thomas J.; Sall, Daniel J. Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 1972 - 1982

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Abstract

In order to determine the active site binding orientation of norepinephrine, a series of conformationally defined analogues of the tyramines, in which the ethylamine side chain is held fixed by incorporation into a benzonorbornene skeleton, were prepared and evaluated for phenylethanolamine N-methyltransferase (PNMT) activity. While exo-2-amino-5-and exo- 2-amino-8-hydroxybenzonorbornene (7 and 10, respectively) were prepared from 5- ...