A novel and easy protocol to obtain 6-alkoxy-Δ-diene-3-one derivatives from available sterols.

Herein we report an unprecedented and efficient methodology for accessing 6-alkoxy-Δ-diene-3-one derivatives. Such scaffolds were serendipitously obtained in the course of the study of the reaction of Δ-3-keto steroids with catalytic amounts of iodine in refluxing methanol. A series of 6-methoxy and 6-ethoxy- Δ-diene-3-ones were prepared from easily-available sterols in a two-step sequence; first, oxidation of sterols furnished the Δ-3-keto steroids, which were then refluxed with ethanol or methanol with I as catalyst to obtain a series of ten derivatives.

In search of cytotoxic selectivity on cancer cells with biogenically synthesized Ag/AgCl nanoparticles.

Green synthesis may be a useful approach to achieve selective cytotoxicity of silver nanoparticles on cancer cells and healthy cells. In this study, the concomitant biosynthesis of silver (Ag)/silver chloride (AgCl) nanoparticles from pineapple peel extracts and their behavior on the breast cancer cell line MCF-7 is shown. Bioreactions were monitored at different temperatures.

Preparation and cytotoxic evaluation of new steroidal oximes and aza-homosteroids from diosgenin and cholesterol.

Using cholesterol and diosgenin as starting materials, we have designed a straightforward methodology to prepare in a reduced number of steps a novel series of steroidal oximes and their aza-homolactam analogs with four types of side chains: cholestane, spirostane, 22-oxocholestane and 22,26-epoxycholestene. The products were evaluated for their cytotoxic activity against the MCF-7 breast cancer cell line. Moreover, the selectivity of the most active compounds was determined against peripheral blood lymphocytes.

Epimerization of C-22 in (25R)- and (25S)-sapogenins.

Most of the naturally occurring steroidal sapogenins (C-23 non-substituted frameworks), possess an R configuration at the spiro C-22 center. Their C-22 epimers have become important targets in biological research. This paper describes a procedure to obtain 22S-spirostans from 22R-sapogenins and pseudosapogenin skeletons, without affecting the chirality at either C-25 or C-20.

Rapid conversion of spirostans into furostan skeletons at room temperature.

We report a facile protocol to obtain 22-substituted furostans and pseudosapogenins in high yields from (25R)- and (25S)-sapogenins. This method involves the treatment of the sapogenin with acetic-trifluoroacetic mixed anhydride and BF(3)·OEt(2) at room temperature, followed by the addition of a nucleophile (H(2)O, MeOH or KSeCN). In the case of 22-hydroxyfurostans, they can be transformed to pseudosapogenins by treatment with p-toluensulfonic acid.

1H and 13C NMR spectral assignment of androstane derivatives.

(1)H and (13)C NMR spectroscopic data for 5alpha-androstanes and halo-5alpha-androstanes with different substituents at positions C-3, C-9, C-11 and C-17 were examined and assigned by a combination of 1D and 2D NMR experiments. The substituent effects on the (13)C chemical shifts were compared with those of epi-androsterone, used as a reference compound. The coupling constants (n)J((19)F,(13)C) were measured for compounds 6, 8, 11 and 14.