Preparation of indole derivatives as melatonin analogs.

Abstract

Derivs. of general formula I [X = NR8, N; Y = C(:W), CWR9; Z = CH, C; R1, R2, R3, R4 = H, OH, alkyl, cycloalkyl, alkoxy, aryloxy, aralkoxy, perhaloalkyl, perhaloalkoxy, halo, NO2, unsatd. aliph. chain; R5 = H, alkyl, aryl, aralkyl, amino, alkoxy, alkyloxycarbonyl, aryloxycarbonyl; R6, R8 = H, alkyl, aryl, aralkyl, alkoxy, etc.; W, R7 = O, S; R9 = alkyl, aryl, alkylcarbonyl, etc.; R5 and R6, R5 and R8, R6 and R8, and R8 and R9 may be linked to form a ring; R1 and R2, R2 and R3, and R3 and R4 may be part of another ring] and cosmetic and pharmaceutical compns. contg. I are disclosed. E.g., stirring a soln. of melatonin in DMSO/12N HCl gave N-[2-(5-methoxy-2-oxo-2,3-dihydroindol-3-yl)ethyl]acetamide. When tested on chicks, the melatonin analogs show a hypnotic effect superior to that of pentobarbital and melatonin and equal to that of diazepam. [on SciFinder(R)]