Convergent synthesis of a steroidal antiestrogen-mitomycin C hybrid using “click” chemistry
Author(s)Hanson, Robert N.; Hua, Edward; Labaree, David; Hochberg, Richard B.; Proffitt, Kyle; Essigmann, John M.; Croy, Robert G.; ... Show more Show less
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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.
Departmentdelete; Massachusetts Institute of Technology. Department of Biological Engineering; Massachusetts Institute of Technology. Department of Chemistry
Organic & Biomolecular Chemistry
Royal Society of Chemistry
Hanson, Robert N., Edward Hua, David Labaree, Richard B. Hochberg, Kyle Proffitt, John M. Essigmann, and Robert G. Croy. “Convergent Synthesis of a Steroidal Antiestrogen-Mitomycin C Hybrid Using ‘click’ Chemistry.” Organic & Biomolecular Chemistry 10, no. 42 (2012): 8501.
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