10455-14-8

Upstream product

• 383911-08-8 4β,5β-dihydroxyandrostan-17-one 
• 383911-07-7 4α,5α-dihydroxy-5α-androstan-17-one 
• 383911-11-3 4α-acetoxy-5α-hydroxyandrostan-17-one 
• 383911-12-4 4β-acetoxy-5β-hydroxyandrostan-17-one 
• 5225-35-4 androst-4-en-17-one 
• 383911-18-0 4-acetoxyandrost-4-en-17-one 
• 58787-77-2 5α-androstane-4α,17β-diol 
• 29220-44-8 (+)-4β-hydroxyandrostan-17-one 
• 50512-79-3 5β-androstane-4,17-dione 

Relevant academic research and scientific papers

Role of hydrophilic interaction in binding of hydroxylated 3-deoxy C19 steroids to the active site of aromatase

As part of our investigation into the structure - activity relationship of a novel class of aromatase inhibitors, C19 steroids having no oxygen function at C-3, we tested aromatase inhibition activity of polar diol compounds 4,19-dihydroxyandrost-5-en-17-ones (25 and 27) and 6,19-dihydroxyandrost-4-en-17-ones (36 and 37). 4α,19-Diol 25 was synthesized from tert-butyldimethylsilyoxyandrost-4-ene steroid (9) through its OsO4 oxidation, giving the 4α,5α-dihydroxy derivative 12, as a key reaction. Acetylation of 5β,6α-dihydroxy-19-acetate 30 and its 5α,6β-analogue 31 followed by dehydration with SOCl2 and alkaline hydroxysis gave 6α,19-diol 36 and its 6βisomer 37, respectively. The stereochemistry of a hydroxy group at C-4 of compound 25 and that at C-6 of compounds 36 and 37 were determined on the basis of 1H NMR spectroscopy in each case. 4β,19-Diol 27, previously synthesized, was identified as an extremely powerful competitive inhibitor of aromatase (Ki = 3.4 nM). In contrast, its 4α,19-dihydroxy isomer 25 and other series of diol compounds, 6,19-dihydroxy-4-en-17-one steroids, were moderate to poor competitive inhibitors (Ki = 110-800 nM). Through this series of analyses, it was concluded that hydrophilic interaction of a 4β,19-diol function with the active site of aromatase plays a critical role in the tight binding of 3-deoxy-5-ene steroids.

Facial selectivity in the hydroboration of androst-4-enes

In the absence of an allylic hydroxy group, the stereochemistry of hydroboration of an androst-4-ene is determined by the presence and stereochemistry of the C-10 methyl group.Allylic hydroxy groups at C-3 direct the hydroboration/oxidation to the anti-face.In the case of the 3α-alcohol, this effect is in opposition to the normal hydration from the α-face of the steroid and leads to the 4β-alcohol.The stereochemistry of 4β,17β-diacetoxy-19-nor-5β-androstane was established by X-ray crystallography.