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Journal articles on the topic 'Androstan'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Yildirim, Kudret, Fatih Gulsan, and Ilknur Kupcu. "Biotransformation of testosterone and progesterone by Penicillium digitatum MRC 500787." Collection of Czechoslovak Chemical Communications 75, no. 6 (2010): 675–83. http://dx.doi.org/10.1135/cccc2009550.

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The biotransformation of testosterone and progesterone by Penicillium digitatum MRC 500787 for 5 days is described. The biotransformation of testosterone afforded 5α-androstane-3,17-dione, 3α-hydroxy-5α-androstan-17-one, 3β-hydroxy-5α-androstan-17-one and androst-4-ene-3,17-dione. The biotransformation of progesterone afforded 5α-pregnane-3,20-dione.

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2

Booth, W. D., and C. A. White. "The isolation, purification and some properties of pheromaxein, the pheromonal steroid-binding protein, in porcine submaxillary glands and saliva." Journal of Endocrinology 118, no. 1 (1988): 47—NP. http://dx.doi.org/10.1677/joe.0.1180047.

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ABSTRACT Pheromaxein, the 16-androstene steroid-binding protein with a relative molecular mass of 15 000 was isolated in sub-milligram quantities from the submaxillary gland and saliva of the Gottingen miniature boar, after a fourfold purification involving the following methods: ultrafiltration for submaxillary gland cytosols and ethanol precipitation for saliva, Concanavalin-A-Sepharose affinity chromatography, sodium dodecyl sulphate polyacrylamide gel electrophoresis, 'Extractigel-D' affinity chromatography (to remove sodium dodecyl sulphate) and fast protein-liquid chromatography. Yields

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3

Bhacca, N., and L. Klasinc. "Photoelectron Spectra and Electronic Structure of Some Steroids." Zeitschrift für Naturforschung A 40, no. 7 (1985): 706–8. http://dx.doi.org/10.1515/zna-1985-0709.

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Gas phase Hel photoelectron spectra of 5ɑ-androstane, 5ɑ-androstan-3-one and 5ɑ-androstan- 17-one compared with those of other saturated cyclic hydrocarbons and ketones indicated that the electronic effect of a keto group in steroids is rather local i.e. extending over about two rings.

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4

Pelecanou, M., and S. Nicolaropoulos. "Notizen: On the Synthesis of D-Homoandrostanes." Zeitschrift für Naturforschung B 48, no. 9 (1993): 1305–6. http://dx.doi.org/10.1515/znb-1993-0924.

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The D-ring expansion of 3 β-hydroxy-5 α-androstan-17-one (epiandrosterone) by the cyanogen azide ring-expansion reaction is described. Epiandrosterone was first converted to 17-methylene-3 β-ydroxy-5 α-androstane by a modification of the Wittig reaction employing methylsulfinyl carbanion-dimethyl sulfoxide. Treatment of the 17-methyleno derivative with cyanogen azide followed by hydrolysis led to 3 β-hydroxy-D-homo-5 α-androstan-17 a-one with migrational selectivity.

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5

Velgová, Helena, and Ladislav Kohout. "6,7-Secoandrostane derivatives." Collection of Czechoslovak Chemical Communications 50, no. 4 (1985): 962–72. http://dx.doi.org/10.1135/cccc19850962.

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6

Kasal, Alexander. "Antiandrogenic A-homo-B,19-dinor-analogues of androgens from 6β-chloro-5-methyl-19-nor-5β-androst-9-enes". Collection of Czechoslovak Chemical Communications 54, № 5 (1989): 1318–26. http://dx.doi.org/10.1135/cccc19891318.

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6β-Chloro derivatives of 5-methyl-19-nor-5β-androst-9-enes (Westphalen diol type) with oxygen functionalities in positions 3 and 17 were converted into diene VI by treatment with lithium aluminium hydride. The lipophilic product of hydrogenation of VI was shown to be 4aα-methyl-A-homo-B,19-dinor-5β,10α-androstane-3β,17β-diol (IX). Various paths leading to dihydrotestosteron analogues, e.g. selective acylation or oxidation of diol IX and partial hydrolysis of diacetate X, have been realized. 17β-Hydroxy-4aα-methyl-A-homo-B,19-dinor-5β,10α-androstan-3-one (XVI) has been found to exhibit antiandr

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7

Crittenden, Christopher M., та Antonio G. DiPasquale. "Two crystallographic forms and the absolute structure of 5α,14α-androstane". Acta Crystallographica Section C Structural Chemistry 77, № 9 (2021): 537–43. http://dx.doi.org/10.1107/s2053229621008408.

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5α,14α-Androstane (C19H32) crystallizes in two different polymorphic forms in the same vapor diffusion experiment. The major form (Form I) crystallizes as thin plates in the space group P21, with Z = 4. These plates are twinned along a long c axis of length 43 Å and readily suffer from radiation damage when diffracted. The minor form (Form II) crystallizes as fine needles in the space group P212121, Z = 3. In the minor form, 5α,14α-androstane cocrystallizes with 5α,14α-androstan-17-one, an oxidation product of 5α,14α-androstane. The presence of 5α,14α-androstan-17-one in the minor form of the

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8

Kohout, Ladislav, and Miroslav Strnad. "Brassinolide analogues without side chain." Collection of Czechoslovak Chemical Communications 54, no. 4 (1989): 1019–27. http://dx.doi.org/10.1135/cccc19891019.

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New brassinolide analogues, characterized by a modified androstane structure without substituent in position 17, were prepared. In the second internode assay, 2α,3α-dihydroxy-B-homo-6-oxa-5α-androstan-7-one (XVII) had the highest brassinoid activity.

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9

Kohout, Ladislav. "Syntheis of brassino steroids with a five carbon atom ester functionality in position 17." Collection of Czechoslovak Chemical Communications 54, no. 12 (1989): 3348–59. http://dx.doi.org/10.1135/cccc19893348.

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Androstane analogues of brassinolide with a five carbon atom ester functionality in position 17 have been prepared. 2α,3α-Dihydroxy-17β-(3-methylbutyryloxy)-7-oxa-B-homo-5α-androstan-6-one (XVIII) exhibited a suprisingly high brassinolide activity.

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10

Al-Fouti, Khaled, та James R. Hanson. "The Stereochemistry of Osmylation of 2- and 17-Methylene-5α-Androstanes". Journal of Chemical Research 2003, № 4 (2003): 232–33. http://dx.doi.org/10.3184/030823403103173606.

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Osmylation of 2-methylene-5α-androstan-17-one has been shown to afford the 2α-hydroxy-2β-hydroxymethyl derivative whilst 3β-hydroxy-17-methylene-5α-androstane gives the 17α-hydroxy-17β-hydroxymethyl derivative; the facial selectivity of these reactions is discussed.

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11

Kasal, Alexander, Barbora Slavíková, Ladislav Kohout, and Miloš Buděšínský. "The Synthesis of A-Homo-B-norandrostanes: The Effect of a Hydroxyl on the Course of Hydrogenation of the ∆9-Double Bond." Collection of Czechoslovak Chemical Communications 62, no. 10 (1997): 1631–41. http://dx.doi.org/10.1135/cccc19971631.

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Acetolysis of 6β-mesyloxy-5-methyl-19-nor-5β-steroids (e.g. 10) was proved to yield 4a-homo-7,19-dinor compounds (e.g. 9) with a hydroxy group in the position 4aα. Hydrogenation of these compounds affords 9β,10β-dihydro derivatives (e.g. 12) predominantly, corresponding 9α,10α isomers (e.g. 13) are only formed in low yields. This sequence was used for the synthesis of analogues of androgen hormones 4aα-hydroxy-4aβ-methyl-4a-homo-7,19-dinor-5α,9β,10β- androstane-3,17-dione (27), 4aα,17β-dihydroxy-4aβ,17α-dimethyl-4a-homo-7,19-dinor-5α,9β,10β-androstan-3-one (28) and 4aα,17β-dihydroxy-4aβ-methyl

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12

Slavíková, Barbora, Alexander Kasal та Ladislav Kohout. "N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide". Collection of Czechoslovak Chemical Communications 63, № 5 (1998): 655–61. http://dx.doi.org/10.1135/cccc19980655.

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3β-Hydroxyandrost-5-en-17-one (1) was converted into 17β-(N-methylamino)androst-5-en-3β-ol (4). In the corresponding N-benzamide 5, structural features characteristic of brassinolide were produced in a standard way, i.e. via 3α,5α-cyclo derivatives 7 and 8, ∆2-olefin 9 and 2α,3α-diol 10. Baeyer-Villiger oxidation yielded two products: 2α,3α-dihydroxy-17β-N-(methylbenzamido)-7-oxa-7a-homo-5α-androstan-6-one (11) and 2α,3α-dihydroxy-17β-(N-methylbenzamido)-6-oxa-7a-homo-5α-androstan-7-one (12).

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13

Murono, Eisuke P. "Differential regulation of steroidogenic enzymes metabolizing testosterone or dihydrotestosterone by human chorionic gonadotropin in cultured rat neonatal interstitial cells." Acta Endocrinologica 122, no. 2 (1990): 289–95. http://dx.doi.org/10.1530/acta.0.1220289.

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Abstract The present studies examined the effects of hCG on steroidogenic enzyme activities involved in the metabolism of testosterone or dihydroststosterone in cultured rat neonatal interstitial cells. 5α-reductase and 17β-hydroxysteroid dehydrogenase activities, which are involved in the conversion of testosterone to dihydrotestosterone and androstenedione, respectively, were low in cultured neonatal interstitial cells, were unresponsive to hCG and declined to undetectable levels during 14 days of culture. However, Δ5-3β-hydroxysteroid dehydrogenase-isomerase activity, which is involved in t

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14

Yildirim, Kudret. "Microbial hydroxylation of some steroids by Aspergillus wentii MRC 200316." Collection of Czechoslovak Chemical Communications 75, no. 12 (2010): 1273–81. http://dx.doi.org/10.1135/cccc2010112.

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Biotransformations of epiandrosterone (1), dehydroepiandrosterone (2) and pregnenolone (3) byAspergillus wentiiMRC 200316 for 5 days have been reported. Incubation of epiandrosterone (1) afforded 11α-hydroxy-5α-androstane-3,17-dione (4) and 3β,11α-dihydroxy-5α-androstan-17-one (5). Incubation of dehydroepiandrosterone (2) afforded 3β,7β-di-hydroxyandrost-5-en-17-one (6) and 3β,7α-dihydroxyandrost-5-en-17-one (7). Incubation of pregnenolone (3) afforded only 11α-hydroxypregn-4-ene-3,20-dione (8).

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15

Černý, Ivan, Vladimír Pouzar, Oldřich Lapčík та Richard Hampl. "Addition of Azoimide to Unsaturated Ketones in the Steroid Series. Synthesis of N-(17β-Hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic Acid and Its Evaluation as Hapten for Dihydrotestosterone Immunoanalysis". Collection of Czechoslovak Chemical Communications 62, № 12 (1997): 1931–39. http://dx.doi.org/10.1135/cccc19971931.

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Addition of azoimide to 17-oxoandrosta-5,15-dien-3β-yl acetate or 17-oxo-5α-androst-15-en-3β-yl acetate gave in both cases corresponding 15β-azido derivatives. 15β-Azido-17-oxo-5α-androstan-3β-yl acetate was selectively reduced to 17β-hydroxy derivative and protected as methoxymethyl ether. Subsequent reduction of azide group and condensation with methyl hydrogen succinate gave a protected succinylamino derivative. Deacetylation and oxidation then led to dihydrotestosterone (DHT) series. Successive removal of protecting groups gave N-(17β-hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic acid, an

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16

Kasal, Alexander. "Antiandrogenic A-homo-B,19-dinorandrostanes from 5β-methyl-19-norandrost-9-enes with different substituents in positions 3 and 17". Collection of Czechoslovak Chemical Communications 54, № 8 (1989): 2218–28. http://dx.doi.org/10.1135/cccc19892218.

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Westphalen-type derivatives II, IV and VIII were converted into derivatives of 4a-methyleno-A-homo-B,19-dinor-5β-androst-9-ene with different substituents in positions 3 and 17 (compounds XII, XIII and XV) which were utilized for the preparation of the antiandrogenic 17β-hydroxy-4aα-methyl-A-homo-B,19-dinor-5β,10α-androstan-3-one (I).

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17

Slavíková, Barbora, Alexander Kasal та Miloš Buděšínský. "Dihydrotestosterone with an Ammonium Centre in the Position 16β". Collection of Czechoslovak Chemical Communications 62, № 4 (1997): 656–64. http://dx.doi.org/10.1135/cccc19970656.

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In an alternative synthesis of 17β-hydroxy-16β-(piperidin-1-yl)-5α-androstan-3-one (4), neighbouring group participation between a 17β-carbonyloxy group and the 16β-amino group was used and a high yield partial hydrolysis of 3β,17β-diacetoxy-16β-(piperidin-1-yl)-5α-androstane (11) was developed. Interference of the neighbouring group participation was also apparent in another 17β-acetoxy derivative - in oxidation of compound 12 to 13. Compound 4 was converted into water-soluble derivatives, i.e. quaternary ammonium derivatives 17 to 20.

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18

Černý, Ivan, Miloš Buděšínský, Pavel Drašar та Vladimír Pouzar. "Construction of the Side-Chain in 14β-Androst-5-ene Derivatives. Preparation of 14β-Pregnenolone". Collection of Czechoslovak Chemical Communications 59, № 12 (1994): 2691–704. http://dx.doi.org/10.1135/cccc19942691.

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Stepwise side-chain construction schemes leading to pregnane derivatives were tested in the 14β-androst-5-ene series. 6β-Methoxy-3α,5-cyclo-5α,14β-androstan-17-one (I) gave after methylenation and hydroboration the 17α-hydroxymethyl derivative III. Subsequent oxidation to the aldehyde VI, Grignard reaction with methylmagnesium iodide, and reoxidation led to the ketone VII and to the isomeric 17β-derivative VIII as a minor product. Final i-steroid cleavage of VII furnished the known 14β,17α-pregnenolone IX; the minor product VIII gave the 17β-isomer X. Alternatively, the ketone X was prepared f

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19

Yildirim, Kudret, Ahmet Uzuner, and Emine Yasemin Gulcuoglu. "Biotransformation of some steroids by Aspergillus terreus MRC 200365." Collection of Czechoslovak Chemical Communications 75, no. 6 (2010): 665–73. http://dx.doi.org/10.1135/cccc2009545.

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The biotransformations of testosterone, epiandrosterone, progesterone and pregnenolone byAspergillus terreusMRC 200365 for five days were described. The biotransformation of testosterone afforded testolactone. The biotransformation of epiandrosterone afforded 3β-hydroxy-17a-oxa-D-homo-5α-androstan-17-one. The biotransformation of progesterone afforded androst-4-ene-3,17-dione and testolactone. The biotransformation of pregnenolone afforded 3β-hydroxy-17a-oxa-D-homoandrost-5-en-17-one and testolactone.

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20

Chodounská, Hana, Alexander Kasal, David Šaman, and Karel Ubik. "One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone." Collection of Czechoslovak Chemical Communications 61, no. 7 (1996): 1037–46. http://dx.doi.org/10.1135/cccc19961037.

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5α-Androstan-17-one and 6β-methoxy-3α,5-cyclo-5α-androstan-17-one were reduced by sodium in deuterium oxide to [16,16,17-2H3]-17β-alcohols. The 17β-tosyloxy group of [16,16,17-2H3]-6β-methoxy-3α,5-cyclo-5α-androstan-17β-ol tosylate was found to be stable under the conditions of the i-steroid rearrangement. The SN2 reaction of the 17β-tosyloxy group with potassium nitrite yielded the corresponding 17α-hydroxy derivative without any loss of deuterium.

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21

Yildirim, Kudret, Ahmet Uzuner, and Emine Yasemin Gulcuoglu. "Baeyer–Villiger oxidation of some steroids by Aspergillus tamarii MRC 72400." Collection of Czechoslovak Chemical Communications 76, no. 6 (2011): 743–54. http://dx.doi.org/10.1135/cccc2011008.

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Biotransformations of epiandrosterone (1), dehydroepiandrosterone (2), testosterone (3), progesterone (4) and pregnenolone (5) byAspergillus tamariiMRC 72400 for 5 days have been reported and the results of these incubations have been compared with previously published data obtained withAspergillus tamariiQM 1223.A. tamariiMRC 72400 showed higher Bayer–Villiger monooxygenase activities thanA. tamariiQM 1223 did. Apart from pregnenolone (5),A. tamariiMRC 72400 metabolized these steroids in different ways. Incubation of epiandrosterone (1) afforded 3β,11β-dihydroxy-5α-androstan-17-one (6) (3%) a

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22

Anthony, A., M. Jaskolski, A. Nangia та G. R. Desiraju. "5β-Androstan-3,17-dione". Acta Crystallographica Section C Crystal Structure Communications 54, № 12 (1998): 1898–900. http://dx.doi.org/10.1107/s010827019800804x.

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23

Södersten, P., P. Eneroth та T. Hansson. "Oestradiol synergizes with 5α-dihydrotestosterone or 3α- but not 3β-androstanediol in inducing sexual behaviour in castrated rats". Journal of Endocrinology 119, № 3 (1988): 461–65. http://dx.doi.org/10.1677/joe.0.1190461.

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ABSTRACT Castrated male rats were treated with constant-release implants filled with testosterone, oestradiol-17β, 17β-hydroxy-5α-androstan-3-one (5α-dihydrotestosterone; DHT), 5α-androstane-3α,17β-diol (3α-Adiol) or 5α-androstane-3β,17β-diol (3β-Adiol). Only testosterone activated the sexual behaviour of the rats. If combined with oestradiol, DHT or 3α-Adiol induced the behaviour, but 3β-Adiol failed to have this effect. Oestradiol inhibited the in-vitro formation of [14C]Adiols from [14C]DHT by combined preoptic and hypothalamic tissue, but only when given in high doses. No effect on the for

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24

Grandgirard, André, Stéphanie Cabaret, Lucy Martine, and Olivier Berdeaux. "New Internal Standard for Quantitative Determination of Oxyphytosterols by Gas Chromatography." Journal of AOAC INTERNATIONAL 87, no. 2 (2004): 481–84. http://dx.doi.org/10.1093/jaoac/87.2.481.

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Abstract A study was conducted to develop a new internal standard for the quantitative determination of oxyphytosterols. Tests on 5α-androsten-3β,17β-diol; 5α-androstan-3β, 17β-diol; 5-pregnen-3β,20α-diol; and 5α-pregnan-3β,20β-diolshowed that these compounds were not fully adequate. However, the compound 3β,22-dihydroxy-20-homo-5-pregnene, synthesized in 4 steps, resulted in a promising internal standard, with a molecule similar to hydroxysterols; retention time as trimethylsilyl in gas chromatography comprised between 5α-cholestane and 7α-hydroxycholesterol; clear mass spectrum in electronic

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25

Černý, Ivan, Vladimír Pouzar, Miloš Buděšínský, and Pavel Drašar. "Synthesis of Symmetrical Bis-Steroid Pyrazines Connected via D-Rings." Collection of Czechoslovak Chemical Communications 65, no. 10 (2000): 1597–608. http://dx.doi.org/10.1135/cccc20001597.

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Bis-steroid pyrazines fused through rings D of the steroid skeleton were synthesized. Methods for the preparation of the corresponding rings A fused derivatives (cephalostatin type) were checked on simple androstanes and then a symmetrical D fused analogue, 5α-androstano[16'',17''-5',6']pyrazino[2',3'-16,17]-5α-androstane-3β,3''b-diol, was prepared. Partially substituted bis-steroid pyrazines in both series were prepared and their use for the preparation of higher fused compounds was discussed. No significant cytostatic activity was found on parent bis-steroid pyrazines both A and D fused.

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26

Li, Wen-Shan, Lokman Torun та Harry Morrison. "Intramolecular sensitization within steroids: Excited-state interaction of C-17 α and β carbonbromine bonds with a C-6 carbonyl group". Canadian Journal of Chemistry 81, № 6 (2003): 660–68. http://dx.doi.org/10.1139/v03-055.

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The synthesis, photochemistry, and photophysics of 17α-bromo-3α-(triphenylsilyloxy)-5α-androstan-6-one (1) and 17β-bromo-3β-(triphenylsilyloxy)-5α-androstan-6-one (2) have been studied in aqueous tetrahydrofuran. The 17α-bromo isomer gives evidence (reduced ϕf, τ1, and ϕisc for the ketone) for interaction between the ketone and CBr moieties in the excited singlet state. Some photodehalogenation is also observed upon excitation of the ketone chromophore. This interaction seems to be absent or minimal for the 17β-bromo isomer.Key words: photodehalogenation, bromosteroid, ketosteroid, intramolec

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27

PENNING, Trevor M., Michael E. BURCZYNSKI, Joseph M. JEZ та ін. "Human 3α-hydroxysteroid dehydrogenase isoforms (AKR1C1–AKR1C4) of the aldo-keto reductase superfamily: functional plasticity and tissue distribution reveals roles in the inactivation and formation of male and female sex hormones". Biochemical Journal 351, № 1 (2000): 67–77. http://dx.doi.org/10.1042/bj3510067.

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The kinetic parameters, steroid substrate specificity and identities of reaction products were determined for four homogeneous recombinant human 3α-hydroxysteroid dehydrogenase (3α-HSD) isoforms of the aldo-keto reductase (AKR) superfamily. The enzymes correspond to type 1 3α-HSD (AKR1C4), type 2 3α(17β)-HSD (AKR1C3), type 3 3α-HSD (AKR1C2) and 20α(3α)-HSD (AKR1C1), and share at least 84% amino acid sequence identity. All enzymes acted as NAD(P)(H)-dependent 3-, 17- and 20-ketosteroid reductases and as 3α-, 17β- and 20α-hydroxysteroid oxidases. The functional plasticity of these isoforms highl

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28

Andrade, L. C. R., J. A. Paixão, M. J. M. de Almeida та ін. "3α,4β-Dihydroxy-5β-androstan-17-one". Acta Crystallographica Section E Structure Reports Online 59, № 1 (2002): o21—o23. http://dx.doi.org/10.1107/s1600536802022055.

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29

Ramos Silva, M., J. A. Paixão, M. J. M. de Almeida, E. J. Tavares da Silva, M. L. Sá e Melo та A. S. Campos Neves. "3β,4α-Dihydroxy-5β-androstan-17-one". Acta Crystallographica Section C Crystal Structure Communications 52, № 11 (1996): 2892–94. http://dx.doi.org/10.1107/s0108270196008839.

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30

Paixão, J. A., M. Ramos Silva, M. J. de Almeida, E. J. Tavares da Silva, M. L. Sá e Melo та A. S. Campos Neves. "3α,4α-Epoxy-5α-androstan-17-one". Acta Crystallographica Section C Crystal Structure Communications 53, № 3 (1997): 347–49. http://dx.doi.org/10.1107/s0108270196014394.

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31

Andrade, L. C. R., J. A. Paixão, M. J. de Almeida, E. J. Tavares da Silva, M. L. Sá e Melo та A. S. Campos Neves. "3β,4β-Epoxy-5β-androstan-17-one". Acta Crystallographica Section C Crystal Structure Communications 53, № 7 (1997): 938–40. http://dx.doi.org/10.1107/s0108270197002138.

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32

Paixão, J. A., L. C. R. Andrade, M. J. de Almeida та ін. "3α,4β-Dihydroxy-5α-androstan-17-one". Acta Crystallographica Section C Crystal Structure Communications 54, № 1 (1998): 89–91. http://dx.doi.org/10.1107/s0108270197009505.

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33

Sroka, A., and I. Majerz. "A ring conformation of androstan-3-one." Molecular Physics 114, no. 13 (2016): 2037–45. http://dx.doi.org/10.1080/00268976.2016.1177220.

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34

Ponsold, Kurt, Michael Hübner, Horst Wagner та Wolfgang Schade. "17α-CH2X-Substituierte Androstan- und 19-Norandrostanderivate". Zeitschrift für Chemie 18, № 7 (2010): 259–60. http://dx.doi.org/10.1002/zfch.19780180710.

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35

Abraham, Raymond J., and M. Ashley Cooper. "A convenient and accurate method for predicting13C chemical shifts in organic molecules." New Journal of Chemistry 42, no. 7 (2018): 5024–36. http://dx.doi.org/10.1039/c8nj00312b.

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36

Kasal, Alexander, Hana Chodounská, and Wojciech J. Szczepek. "trans-Hydrindanes by Reduction: Synthesis of Dihydro-B-nortestosterone." Collection of Czechoslovak Chemical Communications 61, no. 9 (1996): 1386–95. http://dx.doi.org/10.1135/cccc19961386.

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Reduction with diimide was employed in the synthesis of potential antiandrogens - 17β-hydroxy-B-nor-5α-androstan-3-one (26) and its 17α-methyl derivative (25). Other methods of reduction (hydroboration, catalytic hydrogenation) were less effective.

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37

Wölfling, J., G. Schneider, M. Noltemeyer та L. F. Tietze. "3-Methoxy-16,16-dimethyl-5α-androstan-17-one". Acta Crystallographica Section C Crystal Structure Communications 50, № 6 (1994): 964–65. http://dx.doi.org/10.1107/s0108270193012557.

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38

Ramos Silva, M., J. A. Paixão, M. J. M. de Almeida, E. J. Tavares da Silva, M. L. Sá e Melo та A. S. Campos Neves. "3β,4α-Dihydroxy-5β-androstan-17-one. Erratum". Acta Crystallographica Section C Crystal Structure Communications 53, № 3 (1997): 394. http://dx.doi.org/10.1107/s0108270197001510.

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39

Schubert, Gerd, Dieter Tresselt та Manfred Wunderwald. "Synthese von 5α-Androstan-3β,14β,17β-triol". Zeitschrift für Chemie 26, № 10 (2010): 373. http://dx.doi.org/10.1002/zfch.19860261009.

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40

Hilgers, Georg, та Hans-Dieter Scharf. "Synthese von 5β-Androstan-3,17-dion aus Cholsäure". Liebigs Annalen der Chemie 1985, № 7 (1985): 1498–500. http://dx.doi.org/10.1002/jlac.198519850721.

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41

Andrade, L. C. R., J. A. Paixão, M. J. M. de Almeida, F. M. Fernandes Roleira та E. J. Tavares da Silva. "3α,4α-Epoxy-5α-androstan-17β-yl acetate". Acta Crystallographica Section E Structure Reports Online 65, № 4 (2009): o814. http://dx.doi.org/10.1107/s160053680900899x.

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42

Murono, Eisuke P., та Vicki Fisher-Simpson. "Ethanol directly stimulates dihydrotestosterone conversion to 5α-androstan-3α, 17β-diol and 5α-androstan-3β, 17β-diol in rat liver". Life Sciences 36, № 11 (1985): 1117–24. http://dx.doi.org/10.1016/0024-3205(85)90497-7.

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43

Pelli, Beatrice, Pietro Traldi, Michele Gargano, Nicolelta Ravasio та Michele Rossi. "An easy determination of epimeric androsterones by collision spectroscopy: the molar ratio of 5β-androstan-3α-ol-17-one and 5β-androstan-3β-ol-17-one obtained by hydrogenation of 5β-androstan-3,17-dione on Cu/Al2O3 58-Androstan-3,17-dione on Cu/A1203". Organic Mass Spectrometry 22, № 3 (1987): 183–85. http://dx.doi.org/10.1002/oms.1210220314.

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44

Hanson, James R., A. Christy Hunter та Sandrine Roquier. "The Preparation of Some 13α-Androstanes". Collection of Czechoslovak Chemical Communications 63, № 10 (1998): 1646–54. http://dx.doi.org/10.1135/cccc19981646.

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45

Novoa de Armas, Héctor, Oswald M. Peeters, Norbert M. Blaton та ін. "9β,11β-Epoxy-3β-hydroxy-5α-androstan-17-one". Acta Crystallographica Section E Structure Reports Online 57, № 1 (2000): o39—o40. http://dx.doi.org/10.1107/s1600536800018845.

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Abstract:

In the title compound, C19H28O3, the ester linkage in ringAis equatorial. The six-membered ringsAandBhave chair conformations, but ringCcan be better described as a half-chair. The five-membered ringDadopts a 14α-envelope conformation. TheA/B,B/CandC/Dring junctions are alltrans. The packing of the molecules is assumed to be dictated mainly by intermolecular hydrogen bonds. There is an intramolecular C—H...O interaction between the O11 atom of the epoxy group and the methyl C18 group.

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Novoa de Armas, Héctor, Oswald M. Peeters, Norbert M. Blaton та ін. "9α-Chloro-3β,11β-dihydroxy-5α-androstan-17-one". Acta Crystallographica Section E Structure Reports Online 57, № 2 (2001): o166—o167. http://dx.doi.org/10.1107/s1600536801001490.

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47

PAIXAO, J. A., L. C. R. ANDRADE, M. J. DE ALMEIDA та ін. "ChemInform Abstract: 3α,4β-Dihydroxy-5α-androstan-17-one." ChemInform 29, № 18 (2010): no. http://dx.doi.org/10.1002/chin.199818212.

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PAIXAO, J. A., M. RAMOS SILVA, M. J. DE ALMEIDA, E. J. TAVARES DA SILVA, M. L. SA E MELO та A. S. CAMPOS NEVES. "ChemInform Abstract: 3α,4α-Epoxy-5α-androstan-17-one." ChemInform 28, № 26 (2010): no. http://dx.doi.org/10.1002/chin.199726238.

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Shi, Rui, Chun-Sheng Zhang та Kun Wei. "16α-Bromo-17β-hydroxy-5α-androstan-3β-yl acetate". Acta Crystallographica Section E Structure Reports Online 66, № 4 (2010): o750. http://dx.doi.org/10.1107/s1600536810007555.

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50

Merlani, M. I., L. Sh Amiranashvili, N. I. Men’shova та E. P. Kemertelidze. "Synthesis of 5α-androstan-3β,17β-diol from tigogenin". Chemistry of Natural Compounds 43, № 1 (2007): 97–99. http://dx.doi.org/10.1007/s10600-007-0041-1.

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