- CYP11B, CYP17, AND/OR CYP21 INHIBITORS
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Provided herein are inhibitors of CYP11B, CYP17, and/or CYP21 enzymes of Formula (Z), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII). Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of a compound or pharmaceutical composition described herein to treat androgen-dependent diseases, disorders and conditions. Formula (Z)
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Page/Page column 209
(2012/06/30)
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- Synthesis of 14,16-dien-17-yl acetates of androstane series. NMR and mass spectrometry data
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On the basis of dehydroepiandrosterone through the δ14- and δ 15-androst-17-ones a series of androsta-14,16-dienyl acetates was obtained, the key compounds in the synthesis of 14-substituted steroids. By the methods of two-dimensional NMR spectroscopy the structure of compounds was proved and a full assignment of signals in the 1H and 13C NMR spectra was performed. With the use of tandem mass spectrometry the main directions of fragmentation of protonated molecules of the synthesized ketones and dienyl acetates were studied.
- Baranovskii,Bolibrukh,Gromak
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experimental part
p. 1877 - 1885
(2012/01/07)
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- 15β-Hydroxysteroids (Part I). teroids of the human perinatal period: The synthesis of 3β,15β, 17α-trihydroxy-5-pregnen-20-one
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15-Hydroxysteroids have long provided information about fetal well-being and fetal steroidogenesis. 5β,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-trihy
- Reeder, Anthony Y.,Joannou, George E.
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- 15β-Hydroxysteroids (Part VI). Steroids of the human perinatal period: the preparation and reactions of synthesis of 3β-hydroxy-5,15-androstadien-17-one. The synthesis of 3β,15β-dihydroxy-5-androsten-17-one and derivatives
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A successful approach to the synthesis of 3β,15β-dihydroxy-5-androsten-17-one (14d) has been developed using trichloroethoxy ethers as intermediates in the synthesis of the corresponding alcohols. 3β-Methoxymethoxy-5,15-androstadien-17-one (10c) was prepa
- Joannou, George E.,Reeder, Anthony Y.
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- Synthesis of hydroxylated steroid hormones via conjugate addition of a silyl-cuprate reagent
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The synthesis of several hydroxylated steroids via conjugate addition of Fleming's silyl-cuprate reagent, (PhMe2Si)2CuLi, a masked hydroxyl group, to the appropriate enone was studied.By this means 7α-hydroxytestosterone (7) was obtained in good yield from 17β-hydroxyandrosta-4,6-dien-3-one (1a), though similar reactions on 17β-hydroxyandrosta-1,4-dien-3-one (8) gave a low yield of 1α-hydroxytestosterone (13) chiefly through the poor conversion of the phenylsilyl intermediate into the halogenosilane. 3β,16α-Dihydroxy-5α-pregnan-20-one (18b) was obtained in a similar manner from 3β-hydroxy- 5α-pregn-16-en-20-one and 5α-cholestane-1α,3α-diol (17) was produced from the 1-en-3-one (14) via conjugate addition of the silyl group, reduction of the carbonyl function, and oxidative removal of the silyl group. - Keywords: hydroxylated steroids; 7α-hydroxytestosterone; 1α-hydroxytestosterone; 3β,16α-dihydroxy-5α-pregnan-20-one; 5α-cholestane-1α,3α-diol
- Garside, Diana,Kirk, David N.,Waldron, Norman M.
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p. 702 - 711
(2007/10/02)
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- 15-substituted 4-azasteroids
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Compounds of the formula STR1 or a pharmaceutically acceptable salt or ester thereof, wherein R1 is selected from the group consisting of hydrogen and C1-10 alkyl; R2 is selected from the group consisting of hydrogen and C1-10 alkyl; R3 is selected from the group consisting of C1-10 alkoxyl, C1-10 alkyl and cyano; R4 is selected from the group consisting of C1-10 alkenyloxyl, C1-10 alkoxyl, C1-10 alkyl, C1-10 alkylcarbamic, C1-10 alkylcarbonyloxyl, carbonyl, hydroxyl, and --NHR5, and R5 is selected from the group consisting of hydrogen and C1-10 alkylcarbonyl. Such compounds are useful as selective antagonists of testosterone 5α-reductase 1.
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- Synthesis of 15β-Hydroxy-24-oxocholesterol and 15β,29-Dihydroxy-7-oxofucosterol
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3β-Acetoxyandrost-5-en-17-one has been converted into 15β-hydroxy-24-oxocholesterol.Reaction of (17E)-3-β-(dimethyl-t-butylsilyloxy)-15β,16β-epoxypregna-5,17(20)-diene with the magnesium cyanocuprate derivative of 3-(1,3-dioxolan-2-yl)-4-methylpentyl bromide gave (20R)-3β-(dimethyl-t-butylsilyloxy)-15β-hydroxy-24-oxocholesta-5,16-diene 24-ethylene acetal in 80percent yield, and this was converted into the target compound in high yield by catalytic hydrogenation followed by removal of the protecting groups.Reaction of 3β,15β-diacetoxycholest-5-en-24-one with the anion of diethyl cyanomethylphosphonate and reduction of the resulting nitrile with DIBAL-H, gave 15β,29-dihydroxyfucosterol.This was converted into the 3,29-diacetate 15-formate and oxidized with chromium trioxide-3,5-dimethylpyrazole.Removal of the acetate and formate groups with aqueous potassium carbonate afforded 15β,29-dihydroxy-7-oxofucosterol.
- Liu, Dashan,Stuhmiller, Louise M.,McMorris, Trevor C.
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p. 2161 - 2168
(2007/10/02)
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- NEW SYNTHETIC METHODS FOR α,β-UNSATURATED KETONES, ALDEHYDES, ESTERS AND LACTONES BY THE PALLADIUM-CATALYZED REACTIONS OF SILYL ENOL ETHERS, KETENE SILYL ACETALS, AND ENOL ACETATES WITH ALLYL CARBONATES
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Silyl enol ethers and ketene silyl acetals derived from ketones, aldehydes, esters and lactones are converted into α,β-unsaturated ketones, aldehydes and lactones by treatment with allyl carbonates in high yields using the palladium-bis(diphenylphosphino)ethane (dppe) complex as catalyst.Phosphine-free palladium catalyst instead of the palladium-phosphine complex gives a higher selectivity for the preparation of cyclopentenone, cyclooctenone, dienones, α,β-unsaturated esters and lactones.As a solvent, the use of nitriles such as acetonitrile is essential.In other solvents, allylation takes place.Enol acetates derived from ketones are converted into α,β-unsaturated ketones by reaction with allyl carbonate in acetonitrile using the palladium complex and tributyltin methoxide as bimetallic catalysts.
- Minami, Ichiro,Takahashi, Kazuhiko,Shimizu, Isao,Kimura, Tsuneo,Tsuji, Jiro
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p. 2971 - 2978
(2007/10/02)
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- Cardiotonic steroids. Part 11. An Improved Procedure for Preparation of Androst-15-en-17-one Derivatives
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α,β-Unsaturated ketones 3a-3c were prepared from the corresponding saturated ketones (1a-1d) by means of sulfinylation with methyl benzenesulfinate and pyrolysis of intermediate phenylsulfinyl derivatives (2a, 2e, 2f).
- Groszek, Grazyna,Kabat, Marek M.,Kurek, Alicja,Masnyk, Marek,Wicha, Jerzy
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p. 305 - 311
(2007/10/02)
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- A NOVEL PALLADIUM-CATALYZED PREPARATIVE METHOD OF α,β-UNSATURATED KETONES AND ALDEHYDES FROM SATURATED KETONES AND ALDEHYDES VIA THEIR SILYL ENOL ETHERS
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Silyl enol ethers prepared from saturated ketones and aldehydes can be converted to α,β-unsaturated ketones and aldehydes by the reaction of allyl carbonate in the presence of palladium-phosphine complexes as a catalyst.The selection of solvent is crucial and nitriles are most effective as the solvent.
- Tsuji, Jiro,Minami, Ichiro,Shimizu, Isao
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p. 5635 - 5638
(2007/10/02)
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