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Abstract
Here we report the reaction in the biphasic system of the in situ prepared selenols and thiols with 1,4-androstadiene-3,17-dione (1) or prednisone acetate (2) having α,β-unsaturated ketone as an electrophilic functionalization. The Michael-type addition reaction resulted to be chemo- and stereoselective, affording a series of novel steroidal selenides and sulfides. This is an example of a one-step, eco-friendly process that bypasses some of the main concerns connected with the bad smell and the toxicity of these seleno- and thio-reagents. Furthermore, we demonstrated that the proposed methodology offers the possibility to prepare libraries of steroids variously and selectively decorated with different organochalcogen moieties at the C1 position starting from 1,4-androstadienic skeletons and leaving unaltered the C4–C5 unsaturation. Based on the data reported in the literature the introduction of an organoselenium or an organosulfur moiety in a steroid could provide new interesting pharmaceutically active entities exerting anticancer and antimicrobial activities. In this optic, new synthetic strategies to efficiently prepare this class of compounds could be strongly desirable.
Highlights
In the last decades different classes of organoselenium compounds were investigated for biological purposes, evidencing, besides the antioxidant properties [1], some promising activities, such as antiviral, antibacterial and anticancer [2,3]
Improving synthetic tools in order to enable the chemo regio- and stereoselective preparation of novel selenium- and sulfur-containing libraries of steroids is challenging for the exploration of the chemical space in the discovery of novel biologically active compounds
Diphenyldsynthesis of selenoand thiosteroids using chalcogenating reagents generated in situ situ by by synthesis of selenoand thiosteroids using chalcogenating reagents generated in iselenide (3a) and diaryldiselenides bearing both electron withdrawing (3d) or donating the
Summary
In the last decades different classes of organoselenium compounds were investigated for biological purposes, evidencing, besides the antioxidant properties [1], some promising activities, such as antiviral, antibacterial and anticancer [2,3].the cyclopenta[a]phenanthrene skeleton is a privileged core structure present in several pharmacologically relevant molecules as well as in some commercially available drugs and/or hormones such as glucocorticoids, steroidal anti-inflammatories or cardiac steroids [4]. In the last decades different classes of organoselenium compounds were investigated for biological purposes, evidencing, besides the antioxidant properties [1], some promising activities, such as antiviral, antibacterial and anticancer [2,3]. S-moiety to a steroidal structure may have enhanced biological properties when compared to the native fragments [5]. Improving synthetic tools in order to enable the chemo regio- and stereoselective preparation of novel selenium- and sulfur-containing libraries of steroids is challenging for the exploration of the chemical space in the discovery of novel biologically active compounds. Selenium can be contained in functionalized selenoureas [6], or heterocycles such as N-linked selenoxazoles [7] or 1,2,3-selenodiazoles [8] that are generally introduced
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