79316-11-3Relevant articles and documents
SYNTHESIS AND CIRCULAR DICHROISM STUDIES OF STEROIDAL SCHIFF BASES OF BIOGENIC AMINES
Price, Howard C.,Sawutz, David G.,Wagner, Thomas E.,Shewmaker, Chris
, p. 1679 - 1684 (2007/10/02)
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 1Lb Cotton effect (=-1000) near 280nm and a band near 230nm (=+19,000) which is considered the sum of a positive azomethine n-?* Cotton effect and positive aromatic 1La Cotton effect(s).The 1La 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.
