Stereoisomeric indole compounds, process for the preparation...

Details Stereoisomeric indole compounds, process for the preparation... Stereoisomeric indole compounds, process for the preparation...

C - Chemistry, Metallurgy

07

D

C07D 413/04 (2006.01) A61K 31/422 (2006.01)

Patent

CA 2302402

Novel stereoisomeric indole compounds of the formula (1), a process for the preparation the same, and use thereof (SEE FORMULA 1) wherein, Y represents the group (SEE FORMULA 2) (SEE FORMULA 3) wherein, X represents alkyl group having 1-5 carbon atom(s) (the alkyl group may be substituted with hydroxyl group, carboxyl group, amino group, methylthio group, mercapto group, guanidyl group, imidazolyl group or benzyl group), and R1 and R2 represent each independently hydrogen atom, alkyl group, aralkyl group, cycloalkyl group or aryl group; R represents hydrogen atom, alkyl group, aralkyl group, cycloalkyl group, aryl group, monovalent metal, amine or ammonium; and the symbol represents a position of an asymmetric carbon atom. The above-mentioned compounds can be prepared by condensing tryptophan with a stereoisomeric .alpha.-amino acid or carboxylic acid to form an amide form and subjecting or carboxylic acid to form an amide form and subjecting the amide form to oxidative cyclization to form an oxazole ring at once. The compounds exhibit physiological activities such as inhibitory action against lipid peroxidation, and can be therefore utilized in the form of lipid peroxidation inhibitors containing the same as the active ingredient.

Nouveaux composés indoliques stéréo-isomères, représentés par la formule générale (1), dans laquelle Y est (2) ou (3), (* représentant la position d'un atome de carbone asymétrique), [où X est alkyle C1-C5 éventuellement substitué par OH, carboxyle, amino, méthylthio, mercapto, guanidyle, imidazolyle ou benzyle; et R1 et R2 sont indépendamment H, alkyle, aralkyle, cycloalkyle ou aryle]; et R est H, alkyle, aralkyle, cycloalkyle, aryle, un métal monovalent, amine ou ammonium). Pour préparer ces composés, on condense le tryptophane avec un acide alpha -amino ou un acide carboxylique stéréo-isomère, de façon à former un amide; puis en soumet l'amide à une cyclisation oxydative, de façon à former directement un noyau oxazole. Ces composés ayant une activité physiologique, telle que l'inhibition de la peroxydation lipidique, ils peuvent être utilisés comme inhibiteurs de la peroxydation lipidique, dans lesquels ils représentent les principes actifs.

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