20986-46-3

Usage

InChI:InChI=1/C20H28O3/c1-19-11-9-16(21)18(23-3)15(19)5-4-12-13-6-7-17(22)20(13,2)10-8-14(12)19/h12-14H,4-11H2,1-3H3/t12-,13-,14-,19+,20-/m0/s1

Upstream product

• 67-56-1 methanol 
• 63-05-8 Androstenedione 
• 566-48-3 4-hydroxyandrost-4-ene-3,17-dione 
• 74-88-4 methyl iodide 
• 77057-73-9 4,5-epoxyandrostane-3,17-dione 

Downstream Products

• 89593-30-6 4-acetoxy-androsta-4,6-diene-3,17-dione 
• 566-48-3 4-hydroxyandrost-4-ene-3,17-dione 

Relevant academic research and scientific papers

Topical treatment for mastalgia

A composition for medicinal treatment by means of topical administration is described, which contains an aromatase inhibitor, in addition to conventional constituents of topical forms of administration. The active ingredient or the composition containing this active ingredient is especially suitable for the prophylaxis and for the treatment of mastalgia.

Synthesis and Evaluation of a New Series of Mechanism-Based Aromatase Inhibitors

A series of new 4-(alkylthio)-substituted androstenedione analogues was designed as potential suicide inhibitors of aromatase on the basis of mechanistic considerations on the mode of action of the enzyme.Their synthesis and biological evaluation are described.Among the most interesting are the 4--, 4-androstenediones 12, 13, and 14 with respective IC50's of 2.7, 0.8, and 0.94 μM.Compound 12 was a reversible inhibitor of aromatase while compounds 13 and 14 displayed time-dependent kinetics of inhibition with respective KI's and half-times of inactivation of 30 nM and 3.75 min for 13 and 30 nM and 3 min for 14.The inhibition of aromatase by 14 was NADPH-dependent, and was protected by the presence of substrate (0.5-1 μM), while β-mercaptoethanol (0.5 mM) failed to protect the enzyme from inactivation.Dialysis failed to reactivate aromatase previously inactivated by 14.The mechanistic implications of these findings are discussed.

Reactions of Enolizable Steroidal 4-En-3-ones and 17-Ones with Hypervalent Iodine

Reaction of the 3-oxo-4-androsten-derivative 1 or 4 with 1.2 eq. of o-iodosylbenzoic acid in methanolic KOH gave the methoxy products, the 4-methoxide 2 or 5 and the 6β-methoxide 3 or 6, along with dehydrated compound, the 4,6-dienone 7 or 8, respectively.Treatment of the 6-methoxide 3 or 6 with trimethylsilyl iodide yielded the 5α-androstane-3,6-dioxo derivative 11 or 12 in high yield.The same hypervalent oxidation of the 17-oxo steroid 15, 18, 21 or 24 using excess iodine and a longer reaction time produced the corresponding 16α-hydroxy-17,17-dimethylacetal 16, 19,22 or 25, which was converted into the 16α-hydroxy-17-one 17, 20, 23 or 26 by treatment with diluted HCl in every case.Keywords - hypervalent iodine oxidation; o-iodosylbenzoic acid; 4-en-3-oxo steroid; 17-oxo steroid; methoxylation; dehydration; 16α-hydroxy-17,17-dimethoxy steroid; 16α-hydroxy-17-oxo steroid; 5α-saturated 3,6-dioxo steroid

Methoxylation of Enolizable Steroidal 4-Ene-3-ones using Hypervalent Iodine

Reaction of androst-4-ene-3,17-dione (1) with o-iodosylbenzoic acid in methanolic potassium hydroxide gave the methoxylated products, the 4- and 6β-methoxides (2) and (3), along with the dehydrogenated compound, the 4,6-dienone (4).

The Synthesis of 4-Hydroxyandrost-4-ene-3,17-dione and other Potential Aromatase Inhibitors

We describe novel syntheses of 4-hydroxyandrost-4-ene-3,17-dione (Ia) and related compounds, some containing fluorine.In addition we provide further evidence of the general tendency of 2- and 6-substituted androst-4-ene-3,17-diones to undergo rearrangement reactions, and thus provide new routes to 6-fluoro- and 2,6-difluoro-derivatives.Several of these compounds are potent aromatase inhibitors.