235786-79-5

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• 2627-86-3 (S)-1-phenyl-ethylamine 
• 78-84-2 isobutyraldehyde 

Relevant academic research and scientific papers

Diastereoselective addition of allylmetal compounds to imines derived from (S)-1-phenylethanamine

The sense of asymmetric induction and the degree of diastereoselectivity in the addition of allylmetal compounds to imines derived from aldehydes and (S)-1-phenylethanamine is affected by the nature of the imine and of the metal. Allyl-BBN, -MgX, -ZnBr, -Cu, and diallylcuprate attacked the Si face of the imine derived from 2-methylpropanal. Conversely, the Re face of aromatic aldimines was generally attacked, but the behaviour of the magnesium reagent was variable. Best results were achieved with allyl-BBN and diallyl cuprate (de up to 98% at -78°C) with both aliphatic and aromatic imines. However, the use of allylzinc bromide and allyl(dichloro)iodotin was preferable with the bidentate pyridine-2-imine (de 70%, Re face addition). The cleavage of the chiral auxiliary (ammonium formate-palladium on carbon-methanol, 65°C, 2 h) occurred regioselectively, with concomitant hydrogenation of the unsaturated chain, only on the dibenzylic amine obtained by the reactions of (S)-2,5-dimethoxybenzaldimine with allyl-BBN (de 94%) and dially cuprate (de 99%). This allowed the expeditious and efficient synthesis of (R)-(+)-1-(2,5-dimethoxyphenyl)butanamine (80% overall yield) and, at the same time, the confident assignment of the configuration to the homoallylic amines obtained from the aromatic aldimines, previously undetermined. The opposite sense of asymmetric induction observed in the reaction of aliphatic vs. aromatic aldimines was attributed to the isomerization of E- to Z-aromatic imines prior to the C-C bond formation. Several six-membered chair or boat cyclic transition states, featuring different dispositions of the auxiliary and π-stacking of aryl groups, have been empirically examined.

S-SUBSTITUTED N-1- (HETERO)ARYL ALKYL-N - (HETERO)ARYL ALKYLYSOTHIOCARBAMIDES, METHOD FOR THE PRODUCTION THEREOF, PHYSIOLOGICALLY ACTIVE S-SUBSTITUTED N-1- (HETERO )ARYL ALKYL-N - (HETERO)ARYL ALKYLYSOTHIOCARBAMIDES,A PHARMACEUTICAL COMPOUND AND CURING METHOD

The invention relates to s-substituted N-1-[(hetero)aryl]alkyl-N-1-[(hetero)aryl]alkylysothio-carbamides and the physiologically active salts and bases thereof, embodied in the form of racemic mixtures (or stereoisomer mixture) or individual optical isomers. The specific physiological activity of said compounds makes it possible to use them in the form of molecular tools. Said invention also relates to Pharmaceutical compositions, containing said compounds and to a method for preventing and curing various diseases including neurodegenerative diseases as, for example Alzheimer's disease (AD). The pharmacological effect of said compounds is based on the combined cognitive-stimulating and neuroprotective action thereof, which is produced by acting on chemo-controlled calcium channels of neurone membranes, in particular the neurones regulated by glutamate receptors of the central neural system (CNS).