Abstract
A practical and high-yielding Schmidt reaction for the synthesis of fused tetrazoles from bile acid precursors was developed. Mild reaction conditions using TMSN3 instead of hydrazoic acid as an azide source produced good yields of the desired tetrazoles. These conditions could be applied to other steroidal precursors. Additionally, an improved methodology for the synthesis of different ketone and enone precursors from cholic acid, deoxycholic acid, and chenodeoxycholic acid was established. Newly obtained tetrazole derivatives were characterized by NMR and X-ray diffraction spectroscopy. In a number of cases, preliminary antiproliferative tests of new compounds showed strong and selective activity towards certain tumor cell lines.
Highlights
Bile acids are naturally occurring steroidal surfactants that play various biological roles
Besides the well-known role as lipid solubilizers, bile acids are recognized as metabolism regulators through specific receptors: farnesoid X receptor (FXR) and Takeda G protein receptor 5 (TGR5) [1,2,3]
It should be noted that the Schmidt reaction, employing hydrazoic acid, was used in transformations of some steroidal ketones to the corresponding lactams and tetrazoles
Summary
Bile acids are naturally occurring steroidal surfactants that play various biological roles. A practical and high-yielding Schmidt reaction for the synthesis of fused tetrazoles from bile acid precursors was developed. Mild reaction conditions using TMSN3 instead of hydrazoic acid as an azide source produced good yields of the desired tetrazoles.
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