ABSTRACT
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.
Subject(s)
Behavior, Animal/drug effects , Indans/chemical synthesis , Indans/pharmacology , Methylamines/chemical synthesis , Methylamines/pharmacology , Motor Activity/drug effects , Animals , Cocaine-Related Disorders/drug therapy , Indans/chemistry , Indans/therapeutic use , Iodine/chemistry , Male , Methylamines/chemistry , Methylamines/therapeutic use , Molecular Structure , Naphthalenes/chemistry , Random Allocation , Rats , Rats, WistarABSTRACT
[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.
Subject(s)
Hydrogen/chemistry , Indans/chemical synthesis , Iodine/chemistry , Methylamines/chemical synthesis , Naphthalenes/chemistry , Indans/chemistry , Methylamines/chemistry , Molecular Structure , Oxidation-Reduction , Stereoisomerism , TemperatureABSTRACT
With the purpose of preparing latent forms of six naphthylazoderivatives (five of them are schistosomicidal agents), polymers of these chemotherapeutic agents were synthesized in a two-step reaction. First, polymeric 1-methyleneaminonaphthalene (II) was synthesized by condensing 1-naphthylamine with formaldehyde. Subsequently, coupling of II with five sulfonamides (of which four are moieties of schistosomicidal agents) and 5-aminouracil (which is a part of another schistosomidical agent) yielded polymeric 1-methyleneamino-4-naphthylazoderivaties (IIIa-f). In bioligical tests in mice experimentally infected by Schistosoma mansoni, the six new polymers were found inactive.