Convergent synthesis of a steroidal antiestrogen-mitomycin C hybrid using “click” chemistry?

Organic & Biomolecular Chemistry Pub Date: 2012-09-14 DOI: 10.1039/C2OB25902H

Abstract

A convergent synthesis of a novel estrogen receptor-targeted drug hybrid was developed based on structures of the potent anti-proliferative mitomycin C and the steroidal anti-estrogen RU 39411. The steroidal antiestrogen was prepared with an azido-triethylene glycoloxy linker while the mitomycin C derivative (porfirimycin) incorporated a complementary 7-N-terminal alkyne. The two components were ligated using the Huisgen [3 + 2] cycloaddition (“click”) reaction. Preliminary biological assays demonstrated that the final hybrid compound retained both potent anti-estrogenic and anti-proliferative activities.

Graphical abstract: Convergent synthesis of a steroidal antiestrogen-mitomycin C hybrid using “click” chemistry
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