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We report on the syntheses of 1α- and 17α-aminoalkyl dihydrotestosterone (DHT) derivatives and the particularly high binding affinity of the 1α-aminohexyl ligand for human sex hormone-binding globulin (SHBG). The two 17α-aminopropyl-17β-hydroxy-5α-androstan-3-one (1) and 17α-aminocaproylamidoethyl-17β-hydroxy-5α-androstan-3-one (2) derivatives were synthesized via a 17β-spirooxirane intermediate in...
The photoactivable aryl azide reagents, N-(5-azido-2-nitrobenzoyl)oxysuccinimide, 4-azido-1-fluoro-2-nitrobenzene, and 4-azido-1-nitro-2,4,5,6-tetrafluorobenzene have been condensed at the extremity of three 17α-aminomethyl, 17α-aminoethyl, and 17α-aminopropyl side-chains introduced on (17S)-spiro-(3,3-dimethoxy)-5α-androstan-17β,2'-oxirane either directly, by ammonolysis, in the first case, or by...
17α-Aminomethyl, 17α-acetamidomethyl, and 17α-hemiglutaramidomethyl derivatives of dihydrotestosterone and testosterone have been prepared by hydrocyanation of 3,3 -(ethylenedioxy)-5α-androstan-17-one and 3,3 -ethylenedioxyandrost-5-en-17-one, reduction of the corresponding acetylated 17α-cyanohydrins with lithium aluminium hydride, and acylation of the resulting 17α-aminomethyl derivatives with...
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