Abstract
The reactions of selected α,β-unsaturated steroidal ketones with Lawesson’s reagent (LR) in CH2Cl2 and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P4S10/HMDO) in 1,2-dichlorobenzene (ODCB) under microwave irradiation were investigated and for this purpose several cholestane, androstane and pregnane carbonyl derivatives were chosen. Depending on the reagent and the solvent, 19 new sulfur containing compounds, including dithiones 4c and 4d, α,β-unsaturated 3-thiones 3a-e, dimer-sulfides 2a-e, 1,2,4-trithiolanes 5a-e and phosphonotrithioates 6b-e were synthesized. All newly prepared compounds were characterized by IR, 1H- and 13C-NMR spectroscopy and elemental analysis.
Highlights
Steroids are an important group of natural compounds possessing a variety of biological activities.The replacement of one or more carbon atoms in a steroid molecule by a heteroatom affects the chemical properties of that particular steroid and often results in alterations of its biological activity, Molecules 2010, 15 which sometimes may be useful
The addition of heterocyclic rings or new functional groups to steroid molecules often leads to changes in their physiological activity
In this work we showed that Lawesson’s reagent can be suitable for preparation of α,β-unsaturated steroidal thioketones as well as different, depending on the solvent, sulfur steroid derivatives. α,βUnsaturated ketones 1a-e in boiling toluene gave, besides dimer-sulfides 2a-e, the thioketones 3a-e in
Summary
Steroids are an important group of natural compounds possessing a variety of biological activities. The replacement of one or more carbon atoms in a steroid molecule by a heteroatom affects the chemical properties of that particular steroid and often results in alterations of its biological activity, Molecules 2010, 15 which sometimes may be useful. The addition of heterocyclic rings or new functional groups to steroid molecules often leads to changes in their physiological activity. We reported synthesis of 6-thioxo-7-aza-B-homocholest-4-ene and 6-aza-7-thioxo-B-homocholest-4-ene using Lawesson’s reagent [1]. Continuing this investigation and our previous work on modified steroid compounds as biologically active molecules [1,2,3,4], the goal of this study was to synthesize some new thioxosteroid derivatives
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