105186-35-4

Usage

Chemical Properties

White Solid

Uses

A metabolite of Tibolone

Upstream product

• 105186-34-3 10β-hydroperoxy-17β-hydroxy-7α-methyl-19-nor-17α-pregn-4-en-20-yn-3-one 
• 105186-33-2 3,3-dimethoxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-17β-ol 
• 5630-53-5 tibolone 
• 63841-74-7 7α-methyl-3,17-dioxoandrost-4-en-19-al 
• 88247-84-1 3,3-dimethoxy-7α-methylestr-5(10)-en-17-one 
• 105186-32-1 7α-methylestr-5(10)-ene-3,17-dione 

Relevant academic research and scientific papers

Copper-catalyzed vinylogous aerobic oxidation of unsaturated compounds with air

A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters is described. This method features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones. Furthermore, the present catalytic system is suitable for bisvinylogous and trisvinylogous oxidation. Tetramethylguanidine (TMG) was found to be crucial in its role as a base, but we also speculate that it serves as a ligand to copper(II) triflate to produce the active copper(II) catalyst. Mechanistic experiments conducted suggest a plausible reaction pathway via an allylcopper(II) species. Finally, the breadth of scope and power of this methodology are demonstrated through its application to complex natural product substrates.

Method of producing tibolone metabolites by fermentation with Rhizopus stolonifer

A new method of producing metabolites of tibolone comprising fermenting tibolone with Rhizopus stolonifer (ATCC 12938) resulting in the formation of Δ4-Tibolone (C21H28O2), 6β-Hydroxytibolone, and 15β-Hydroxytibolone (C21H28O3) is reported.

Alpha-glucosidase and tyrosinase inhibitors from fungal hydroxylation of tibolone and hydroxytibolones

Sixteen new and one known metabolites 4-20 were obtained by incubation of tibolone (1) and hydroxytibolones (2 and 3) with various fungi. Their structures were elucidated by means of a homo and heteronuclear 2D NMR and by HREI-MS techniques. The relative stereochemistry was deduced by 2D NOESY experiment. Metabolites of tibolone (1) exhibited significant inhibitory activities against α-glucosidase and tyrosinase enzymes. Hydroxylations at C-6, C-10, C-11, C-15 positions and α,β-unsaturation at C-1/C-2, C-4/C-5 showed potent inhibitory activities against these enzymes.