4-Androstene-3,6,17-trione

Androstene-3,6,17-trione has been described as an irreversible inhibitor of AR [191] with a range of apparent values 1250 [192], 430 [160] and 250 nM [165]. The work that reported an apparent A" = 430 nM also recorded a inact = 4.03 X 10 s . The group reporting the inhibition at a of 1,250 nM also reported the reduced product 3) -hydroxyandrostene-17-one to be a less potent irreversible inhibitor, with a of 6,250 nM both compounds... [Pg.279]

Covey DF, Hood WF (1981) Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and l,4,6-androstatriene-3,17-dione cause a time-dependent decrease in human placental aromatase activity. Endocrinology 108 1597 1599... [Pg.877]

A -Androsten-3,17-dione (S-22), la-cyano-A -androsten-3,17-dione (S-37), ljS-acetylthio-A -androstene-3,17-dione (S-38), 7a-methyl-A -androstene-3,17-dione (S-23), A -androstene-3,l 1,17-trione (S-43), 11/3-hydroxy-A -androstene-3,17-dione (S-44), 3a -hydroxyandrostane-17-one (D-27), 3/3-hydroxyandrostane-I7-one (D-161), and androstane-3,17-dione (D-30) compared to the corresponding 17/3-hydroxy derivatives exhibit much smaller androgenic and anabolic activities with unfavorable anabolic-androgenic ratios (with the exception of S-23, which has a favorable ratio). [Pg.81]

Tosic acid has been used similarly for the preparation of ethylenethioketals. It is a milder catalyst than boron fluoride etherate for condensation of a ketone with ethanedithiol and has been used, in acetic acid solution, for selective conversions, for example of A -androstene-3,ll,17-trione (0.60 g.) into the 3-ethyleneketal (0.40g.). ... [Pg.590]

A -5-Androstadiene-3,17-dione, 461, 462 5 -Androstane-17/S-ol, 377 5a-Androstane-16-one, 243 5< -Androstane-17-one, 243 5a-Androstane-3-one-17fl-ol, 377 Androstanol-3j8, 363 Androstanone-3, 363 A -Androstene-3, 17-dione, 165 A5-Androstene-3/3-ol, 73 A4-Androstene-3,l 1,17-trione, 354 1 Androsterone, 286... [Pg.259]

Simultaneous 4-androstene-3,ll,17-trione, cortisone, cortisone acetate... [Pg.733]

Watanabe, Y., Ishimura, Y. (1989). A model study on aromatase cytochrome P-450 reaction Transformation of androstene-3,17,19-trione to 10P-hdroxyester-4-ene-3,17-... [Pg.557]

In their total synthesis of 6-methyl-5-androstene-3,l 1,17-trione 3-ethylene acetal, which is a building block for 6a-methylprednisolone, Daniewski and co-workers used a modified Wichterle reaction to install the A-ring of the natural product/ A racemic mixture of 56 was used in a reductive alkylation with Wichterle s reagent to afford the product 57 as a mixture that could be separated by chromatography. Upon treatment of each diastereomer of 57 with formic acid and perchloric acid to induce cyclization, it was observed that both diastereomers resulted in the same enantiopure product 58. This preferred conformation of the steroidal skeleton was confirmed by comparison to an authentic sample of the product that can be obtained directly from natural cortisone. [Pg.509]

Where the nature of the carbonyls of a dicarbonyl compound differ greatly, one isomer of the monodithiolane may become the only product. In the conversion of 4-androstene-3,ll,17-trione to 4-androstene-3,11,17-trione-3-(l,3-dithiolane),no bis- or trisdithiolane was observed (equation 6) The condensation of an equimolar amount of 1,2-ethanedithiol with... [Pg.274]

During the mechanistic studies of estrogen biosynthesis, selective oxidation of androstene-3,17,19-trione (n) to the corresponding carboxylic acid was found to proceed by iron porphyrin complexes (Scheme 14A) [253]. On the basis of substituent effect on the benzaldehyde oxidation and kinetic isotope effect, direct hydrogen abstraction mechanism has been proposed [254]. The relative reactivity of aldehydes and alkenes is as follows cyclooctene, styrene > aldehyde, terminal alkene > a, 3-unsaturated ketone. [Pg.248]

Adrenosterone Sftll/S-Dihydroxyandro-A -Androstene-3,11,17-trione stane-17-one... [Pg.382]

Androatene-3,17-dione 4-Androstene-3,11,17-trione 1 Ij8-Hydroxy-4-aiidrost.eiie-3,17-dione 5a-Androstane-3,17-dione 5i8-Androstane-3,17-dione 15a-Hydroxy-4-aiidrostene-3,17-dione 16a-Hydroxy-4-androslene-3,17-dione... [Pg.157]

Androsten-3,16,17-trione 3a-Hydroxy-5 aiidrt tane-ll, 17-rKone 3tt-Hydr xy-5a-aiidrostane-11,17-dione 3a, 1 lp-Dihydroxy-5 androstan-17-one 3 , 11 )S-1 )ihydro -5a-androstan-l 7-one 3-Oxo-A-aiidrosten-17 yl-sulfatc l7 -Hydioxy-5-androsten-3/3-yl-sulfate l7-Oxo-5a-androstan-3a-yl-sulfate... [Pg.157]

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