The scope and limitations of the reaction of δ5-steroids with mercury(II) trifluoroacetate

Ruddock, Peter L.D; Williams, David J.; Reese, Paul B.

doi:10.1016/s0039-128x(98)00076-2

Cited by 8 publications

(2 citation statements)

References 35 publications

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“…[α] D 25 = −4.92 (c = 0.2; CH 2 Cl 2 ), mp = 163–164 °C (hexane) (lit. [α] D = −4.26 (c = 0.09) mp = 164.5–165 °C [ 34 ]).…”

Section: Methodsmentioning

confidence: 99%

The Effects of the Steroids 5-Androstenediol and Dehydroepiandrosterone and Their Synthetic Derivatives on the Viability of K562, HeLa, and Wi-38 Cells and the Luminol-Stimulated Chemiluminescence of Peripheral Blood Mononuclear Cells from Healthy Volunteers

Sokolov,

Rozhkov,

Uspenskaya

et al. 2024

Biomolecules

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In order to evaluate the role of substituents at 3-C and 17-C in the cytotoxic and cytoprotective actions of DHEA and 5-AED molecules, their derivatives were synthesized by esterification using the corresponding acid anhydrides or acid chlorides. As a result, seven compounds were obtained: four DHEA derivatives (DHEA 3-propionate, DHEA 3-butanoate, DHEA 3-acetate, DHEA 3-methylsulfonate) and three 5-AED derivatives (5-AED 3-butanoate, 5-AED 3,17-dipropionate, 5-AED 3,17-dibutanoate). All of these compounds showed micromolar cytotoxic activity toward HeLa and K562 human cancer cells. The maximum cytostatic effect during long-term incubation for five days with HeLa and K562 cells was demonstrated by the propionic esters of the steroids: DHEA 3-propionate and 5-AED 3,17-dipropionate. These compounds stimulated the growth of normal Wi-38 cells by 30–50%, which indicates their cytoprotective properties toward noncancerous cells. The synthesized steroid derivatives exhibited antioxidant activity by reducing the production of reactive oxygen species (ROS) by peripheral blood mononuclear cells from healthy volunteers, as demonstrated in a luminol-stimulated chemiluminescence assay. The highest antioxidant effects were shown for the propionate ester of the steroid DHEA. DHEA 3-propionate inhibited luminol-stimulated chemiluminescence by 73% compared to the control, DHEA, which inhibited it only by 15%. These data show the promise of propionic substituents at 3-C and 17-C in steroid molecules for the creation of immunostimulatory and cytoprotective substances with antioxidant properties.

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“…[α] D 25 = −4.92 (c = 0.2; CH 2 Cl 2 ), mp = 163–164 °C (hexane) (lit. [α] D = −4.26 (c = 0.09) mp = 164.5–165 °C [ 34 ]).…”

Section: Methodsmentioning

confidence: 99%

The Effects of the Steroids 5-Androstenediol and Dehydroepiandrosterone and Their Synthetic Derivatives on the Viability of K562, HeLa, and Wi-38 Cells and the Luminol-Stimulated Chemiluminescence of Peripheral Blood Mononuclear Cells from Healthy Volunteers

Sokolov,

Rozhkov,

Uspenskaya

et al. 2024

Biomolecules

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show abstract

“…The scope and limitations of the reaction of ∆ 5 -steroids with mercury() trifluoroacetate have been explored. 37 Some unusual products have been obtained 38 from the Woodward-Prevost reaction of diosgenin and its 4β-hydroxy derivative 18 (Scheme 2). These include the tetraol 19, the diosphenol 20 and the aldehyde 21.…”

Section: Alkenesmentioning

confidence: 99%