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15-Hydroxysteroids have long provided information about fetal well-being and fetal steroidogenesis. 3β,15β,-17α-Trihydroxy-5-pregnen-20-one (1a) is a major 15β-hydroxylated metabolite unique to the human perinatal period. The synthesis of 3β,15β,17α-trihydroxy-5-pregnen-20-one (1a) is reported here in the first of a series of publications on the chemical synthesis of 15β-hydroxylated steroids for...
The mare possesses unique steroid hormone metabolic activity during pregnancy in that peripheral 4-pregnene-3,20-dione (progesterone; P4) is undetectable by 220 days gestation. This study examines in vivo metabolism of progestins by the pregnant mare and in vitro metabolic activity of maternal and fetal tissues. Pregnant mares (n = 3) received intravenous infusions of 3β-hydroxy-5-pregnen-20-one...
The syntheses of three classes of C-3 perfluoroalkyl substituted steroids are described. They are the 3β-hydroxy-3α-perfluoroalkylandrost-4-en-17-ones (5a-c), 3-perfluoroalkylandrosta-3,5-dien-3-ones (8a-c) and 3β-hydroxy-3α-perfluoroalkylandrost-5-en-17-ones (12a-c). Addition of a series of perfluroalkylorganometallic reagents (R F Li; R F = C 2 F 5 , C 3 ...
Reaction of 3β-hydroxyandrosta-5,15-dien-17-one with 4-methoxybenzyl alcohol followed by acetylation gave mainly 15β-[(4-methoxyphenyl)methoxy]-17-oxoandrost-5-en-3β-yl acetate. This product was transformed by borohydride reduction and organosilyl derivatization into the orthogonally protected 17β-(dimethylthexylsiloxy)-15β-[(4-methoxyphenyl) methoxy]androst-5-en-3β-yl acetate and 17β-(dimethylisopropylsiloxy)-15β-[4-methoxyphenyl)methoxy]androst-5-en-3@...
Steroids hydroxylated at C-15 have long provided useful information about the well-being of the fetus and feto-placental unit in human pregnancy. In an attempt to develop a new and reliable immunoassay method for use in newborn screening programs for congenital adrenal hyperplasia, we report the chemical synthesis of 3α,15β,17α-trihydroxy-5β-pregnan-20-one (2) from 3α-hydroxy-5β-androstan-17-one...
Mixtures of 3E and 3Z isomers of 3-(O-(2-carboxyethyl))oxime (CEO) derivatives of testosterone and 17α-methyltestosterone were prepared by reaction with (O-(2-carboxyethyl))hydroxylamine. These isomers were separated after conversion into methyl esters, and mild alkaline hydrolysis recovered pure E/Z-isomers of 3-CEO derivatives of testosterone and 17α-methyltestosterone. By the same method, after...
The vertebrate pineal gland rhythmically produces melatonin, a hormone involved in regulation of several physiological and behavioral processes. Melatonin is synthesized from serotonin essentially by two enzymatic steps involving N-acetyltransferase (NAT) and hydroxyindole-O-methyltransferase activities. We have previously demonstrated the presence of melatonin binding sites in the rat testes, and...
Glucocorticoids regulate the activity of the hypothalamic-pituitary-adrenal axis through both mineralocorticoid (MR) and glucocorticoid (GR) receptors in the hippocampus. In addition, glucocorticoids down-regulate hippocampal expression of MR and GR mRNA and protein, presumably decreasing their own effect. Marmosets are a New World primate characterized by extraordinarily high levels of circulating...
3-Methoxy-14α, 15α-methylenestra-1,3,5(10),8-tetraen-17α-ol on hydrogenation with triethylsilane/trifluoroacetic acid yielded 3-methoxy-14β,15β-methylenestra-1,3,5(10)-trien-17α-ol, not the 14α,15α-methylene-9βproduct as previously described . (Steroids 61:48-49, 1996)
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