Recent syntheses of steroid derivatives using the CuAAC “click” reaction

Malika Ibrahim-Ouali,Frédéric Dumur

doi:10.24820/ark.5550190.p011.543

Abstract

The introduction of heterocycles into steroids is often at the origin of a modification of their physiological activity and thus allows the formation of new biologically interesting molecules. Recent advances in the field of steroid synthesis using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) are presented here. Compounds exhibiting known biological activities are also reported in this review. This approach holds great promise and allows us to consider preparing new, highly functionalized complex molecules using the CuAAC click reaction.

Highlights

Biological evaluation of all conjugates synthesized was realized in vitro through MTT assays for antiproliferative activity against a panel of human adherent cell lines (HeLa, MCF-7, and A2780)
Van Liera et al.[33] described the synthesis of estrogen, testosterone- and 19-nortestosterone conjugates linked to BODIPY (4,4-difluoro-4-bora-3α,4α-diaza-s-indacene) or aza-BODIPY to obtain receptor-based fluorescence ligands for imaging breast and prostate cancer
Their synthesis is based on coupling of iodo derivatives of differently substituted BODIPY and aza-BODIPY analogs and steroid alkynes using the click reaction conditions

Summary

Introduction

Biological evaluation of all conjugates synthesized was realized in vitro through MTT assays for antiproliferative activity against a panel of human adherent cell lines (HeLa, MCF-7, and A2780). Their synthesis is based on coupling of iodo derivatives of differently substituted BODIPY and aza-BODIPY analogs and steroid alkynes using the click reaction conditions. Two covalently coupled conjugates 7 and 9 were synthesized in good yields from azidoBODIPY 6 and steroid alkynes 5 and 8 (Scheme 2).

Results

Conclusion