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Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction.

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.

SUBMITTER: Skoric DĐ

PROVIDER: S-EPMC8551880 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction.

Škorić Dušan Đ DĐ Klisurić Olivera R OR Jakimov Dimitar S DS Sakač Marija N MN Csanádi János J JJ

Beilstein journal of organic chemistry 20211020

A practical and high-yielding Schmidt reaction for the synthesis of fused tetrazoles from bile acid precursors was developed. Mild reaction conditions using TMSN<sub>3</sub> 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 estab ...[more]

PMID: 34760027

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