SYNTHESIS AND CIRCULAR DICHROISM STUDIES OF STEROIDAL SCHIFF BASES OF BIOGENIC AMINES

Article abstract of DOI:10.1016/S0040-4020(01)98930-6

A number of imines (Schiff bases) have been prepared from ketosteroids (estrone, estrone-3-methyl ether, andosterone, epiandrosterone, 5α-cholestan-3-one, 6-ketocholestanol and testosterone) and primary amines (phenethylamine, tyramine and hexanamine).The CD spectra of these compounds have been measured in methanol.Except for the testosterone imines, the azomethine n-?^* band (ca. 235nm) exhibited the same sign (but not as high an ellipticity) as the parent ketone's n-?^* band (ca. 295nm).The imines of the estrogens (estrone and estrone 3-methyl ester) gave CD spectra characterized by a negative ¹L_b Cotton effect (<Θ>=-1000) near 280nm and a band near 230nm (<Θ>=+19,000) which is considered the sum of a positive azomethine n-?^* Cotton effect and positive aromatic ¹L_a Cotton effect(s).The ¹L_a band originating in the amine moiety was prominent in the CD of 5α-cholestan-3-one and 6-ketocholestanol phenethylamine imines.When aromatic Cotton effects originating in the amine moiety were detected, they were of the same sign as the n-?^* Cotton effect.