Sterols. IX. The Selective Halogenation and Dehalogenation of Certain Steroids (Part 1)

Julian, Percy L.; Karpel, William J.

doi:10.1021/ja01157a098

Cited by 53 publications

(13 citation statements)

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“…Merck-Schuchardt) was used for column chromatography. Starting materials 1 6 and 2a-f 7 were prepared by literature procedures. All other reagents are commercially available and were used as received.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1'-arylcarbamoylthiocarbonyl-3'-methyl-3-oxo-androst-4-eno[16α,17α-d]pyrazolines

Заварзин¹,

Kamernitsky²,

Chertkova³

et al. 2008

Arkivoc

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Section: Methodsmentioning

confidence: 99%

Synthesis of 1'-arylcarbamoylthiocarbonyl-3'-methyl-3-oxo-androst-4-eno[16α,17α-d]pyrazolines

Заварзин¹,

Kamernitsky²,

Chertkova³

et al. 2008

Arkivoc

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“…In a 25 mL round bottomed flask, fitted with septa and magnetic stirring and under nitrogen atmosphere, Zn-Cu pair (217 mg, 3.32 mmol), freshly prepared (by deposition of Cu 0 , from CuSO 4 , on Zn powder) [26] was placed. Acetonitrile, 5 mL, (dried by distillation over calcium hydride) was added resulting black suspension was stirred for 5 min in a cooling bath until the work temperature was reached (usually 0 C or À44 C).…”

Section: Cycloaddition Reaction Proceduresmentioning

confidence: 99%

Generation of Oxyallyl Cations by Reduction of α,α′-Diiodoketones Under Sonochemical or Thermal Conditions: Improved Methodology for the [4C(4π;)+3C(2π;)] Cycloaddition Reactions

Montaña

Grima

2003

Synthetic Communications

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An improved methodology to carry out [4C(4p)þ3C(2p)] cycloaddition reactions of dienes and oxyallyl cations, is presented. The reaction starts from commercially available dienes and easy-handling a,a 0 -diiodoketones, which are reduced by Zn (powder) or Zn/Cu couple to generate an oxyallyl cation as an intermediate. The reaction is carried out under mild thermal or sonochemical conditions at low temperatures (from 0 to À44 C) and for short reaction times (<15 min).

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“…В работе использованы: прегненолон 1, кетоконазол 2, дидодецилдиметиламмоний бромид (DDAB), боргидрид натрия, Тритон Х-100 и золотохлористоводородная кислота, полученные от фирм "Sigma" и "Aldrich"; препарат рекомбинантного человеческого цитохрома Р450 17А1 (0,108 мкг/мкл), полученный от "Novus Biological" и соединения 3-5, синтезированные известными методами [20,21]. Синтез коллоидного раствора золота (наночастиц золота), стабилизированного DDAB проводили согласно [22].…”

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Screening of potential substrates or inhibitors of cytochrome P450 17a1 (CYP17a1) by electrochemical methods

et al. 2011

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The electrochemical reduction of the recombinant form of human cytochrome P450 17A1 (CYP17A1) was investigated. Hemeprotein was immobilized on electrode modified with biocompatable nanocomposite material based on the membrane-like synthetic surfactant didodecyldimethylammonium bromide (DDAB) and gold nanoparticles. Analytical characteristics of DDAB/Au/CYP17A1 electrodes were investigated with cyclic voltammetry, square wave voltammetry, and differential pulse voltammetry. Analysis of electrochemical behaviour of cytochrome P450 17A1 was conducted in the presence of substrate pregnenolone (1), inhibitor ketoconazole (2), and in the presence of synthetic derivatives of pregnenolone: acetylpregnenolone (3), cyclopregnenolone (4), and tetrabrompregnenolone (5). Ketoconazole, azole inhibitor of cytochromes P450, blocked catalytic current in the presence of substrate pregnenolone (1). Compounds 3-5 did not demonstrate substrate properties towards electrode/CYP17A1 system. Compound 3 did not block catalytic activity towards pregnenolone, but compounds 4 and 5 inhibited such activity. Electrochemical reduction of CYP17A1 may serve as an adequate substitution of the reconstituted system which requires additional redox partners - for the exhibition of catalytic activity of hemoproteins of the cytochrome P450 superfamily.

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Sterols. IX. The Selective Halogenation and Dehalogenation of Certain Steroids (Part 1)

Cited by 53 publications

References 0 publications

Synthesis of 1'-arylcarbamoylthiocarbonyl-3'-methyl-3-oxo-androst-4-eno[16α,17α-d]pyrazolines

Synthesis of 1'-arylcarbamoylthiocarbonyl-3'-methyl-3-oxo-androst-4-eno[16α,17α-d]pyrazolines

Generation of Oxyallyl Cations by Reduction of α,α′-Diiodoketones Under Sonochemical or Thermal Conditions: Improved Methodology for the [4C(4π;)+3C(2π;)] Cycloaddition Reactions

Screening of potential substrates or inhibitors of cytochrome P450 17a1 (CYP17a1) by electrochemical methods

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