Rauwolfia Alkaloids. XXXI.¹ The Synthesis and Activity of Some Reserpine Analogs²

Abstract

due from acetone yielded a second solid product (900 mg.). Two recrystallizations of the second product from alcoholether gave colorless rods (740 mg.), m.p. 265-266°dec., [«]23d -5°( c 1.25, pyr.), 246 µ (e 600).™

Inhibition of Norepinephrine Transport and Reserpine Binding by Reserpine Derivatives

“…To characterize the interaction between reserpine and the amine transporter and to use reserpine as a probe of the transporter, it is instructive to compare the effects of a variety of reserpine derivatives. When the structure of reserpine was determined in the 1950s (Dorfman et al, 1954), many derivatives were synthesized and tested for pharmacological effects (Lucas et al, 1959). Kirshner (1965) tried some of these compounds on isolated chromaffin vesicles and reported that their effectiveness as inhibitors of norepinephrine uptake correlated with their catecholamine-depleting potency in vivo.…”

Stereochemical Factors Related to the Potency of Anticholinergic Psychotomimetic Drugs

“…Since there are only three such interactions which are due to the methyl groups for XXIV, interaction with an electrophilic center may occur primarily in this somewhat less hindered conformational form. Finally, the glycolate esters of 1,2,2,6,6-pentamethyl- 4-piperidinol (VII), which are virtually devoid of psychotogenic activity, can be seen to have a highly hindered amino nitrogen. An approaching electrophilic center would be subjected to four 1,3-diaxial nonbonded interactions in each of the two possible…”

Reduced Sedative Effect of a Newly Synthesized Reserpine Derivative (Syrosingopine): Clinical Appraisal in Primary Hypertension

“…A series of chemical modifications were made by replacing different organic acids at the trimethoxybenzoic‐acid portion of reserpine (6). As a result, a new substance was found which had the cardiovascular effects of reserpine, yet had minimal sedating activity.…”