19202-72-3Relevant articles and documents
Investigations on photochemical linking of steroids with amino acids: Irradiation of α, β-unsaturated steroidal ketones in the presence of amino acids in aqueous medium
Ishar,Girdhar,Kumar,Rama,Kaur
, p. 1253 - 1261 (2007/10/03)
Irradiation of 1, 4-cholestadien-3-one 1 in THF-H2O solvent in the presence of amino acids (glycine/alanine) leads to dienone-phenol photorearrangement products, 3-hydroxy-1-methyl-19-norcholesta-1, 3, 5 (10) - triene 3 (35%), 4-hydroxy-2-methyl-19-nor-cholesta-1, 3, 5 (10)-triene 4 (15%), 1-hydroxy-4-methyl-19-norcholesta-1,3,5(10)-triene 5 (28%) along with a novel methyl substituted-19-norcholesta-1, 3, 5 (10)-triene 6 and a spirocyclic-enone 7; no amino acid or solvent addition product is obtained. Irradiation of 16-dehydropregnenolone-3β-acetate 2 under identical conditions in the presence of glycine affords the pregnenolone-3β-acetate 9 (25%), 16-(tetrahydrofuran-2-yl) -pregnenolone-3β-acetate 10 and its 17α- isomer 11 (together 35%) and 16-(glycin-2-yl) -pregnenolone-3β-acetate 12 (mixture of isomers, 25%). The results are compared and contrasted with known photochemical behaviour of steroidal enones and dienones. The studies indicate that steroidal-16-ene-20-ones can be better photoaffinity labelling agents for progestogen and possibly, adrenal steroidal receptors. Also, the photochemical additions to Δ16-20-one steroidal systems can be exploited for the introduction of substituents/moieties at C16 in steroids.
