Synthesis and circular dichroism studies of steroidal schiff bases of biogenic amines |
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Authors: | Howard C Price David G Sawutz Thomas E Wagner Chris Shewmaker |
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Institution: | Department of Chemistry, Marshall University, Huntington, WV 25701, U.S.A.;Department of Chemistry, Ohio University, Athens, OH 45701, USA |
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Abstract: | A number of imines (Schiff bases) have been prepared from ketosteroids (estrone, estrone-3-methyl ether, androsterone, 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-π* band (~ 235 nm) exhibited the same sign (but not as high an ellipticity) as the parent ketone's n - π* band (~295 nm). The imines of the estrogens (estrone and estrone 3-methyl ether) gave CD spectra characterized by a negative 1Lb Cotton effect (θ] ? -1000) near 280 nm and a band near 230 nm (θ] ? +19,000) which is considered the sum of a positive azomethine n - π* 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 - π* Cotton effect. |
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