RESUMEN
A new approach for the synthesis of indatraline was developed using as the key step an iodine(III)-mediated ring contraction of a 1,2-dihydronaphthalene derivative. Behavioral tests were conducted to evaluate the effect of indatraline and of its precursor indanamide on the motor activity of Wistar rats. Specific indexes for ambulation, raising and stereotypy were computed one, two and three hours after i.p. drug administration. Indatraline effects on motor activity lasted for at least three hours. On the other hand, no significant differences in motor activity were observed using indanamide. The results suggest that indatraline has a long lasting effect on motor activity and add evidence in favor of the potential use of that compound as a substitute in cocaine addiction.
Asunto(s)
Conducta Animal/efectos de los fármacos , Indanos/síntesis química , Indanos/farmacología , Metilaminas/síntesis química , Metilaminas/farmacología , Actividad Motora/efectos de los fármacos , Animales , Trastornos Relacionados con Cocaína/tratamiento farmacológico , Indanos/química , Indanos/uso terapéutico , Yodo/química , Masculino , Metilaminas/química , Metilaminas/uso terapéutico , Estructura Molecular , Naftalenos/química , Distribución Aleatoria , Ratas , Ratas WistarRESUMEN
[reaction: see text] A new approach for the synthesis of (+/-)-indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by PhI(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.