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Steroidal alkenylphosphonates via palladium-catalyzed coupling reactions
R Skoda-Földes1, L Kollár, J Horváth
1University of Veszprém, Department of Organic Chemistry, Hungary.
Steroids
|December 1, 1995
Summary
This study synthesized novel androst-16-ene derivatives with phosphonate groups, showing potential as 5 alpha-reductase inhibitors. The research optimized palladium-catalyzed coupling reactions using excess dialkyl phosphites as solvents.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Steroid Chemistry
Background:
- Steroids are crucial in biological processes.
- 5 alpha-reductase inhibitors are important therapeutic targets.
Purpose of the Study:
- To synthesize novel androst-16-ene derivatives with phosphonate groups.
- To explore palladium-catalyzed coupling reactions for steroid modification.
- To evaluate the potential of synthesized steroids as 5 alpha-reductase inhibitors.
Main Methods:
- Palladium-catalyzed coupling of 17-iodo-delta 16 steroids with dialkyl phosphites.
- Solvent-free reaction conditions utilizing excess dialkyl phosphite.
- Characterization of synthesized steroid derivatives.
Main Results:
- Eight new androst-16-ene derivatives with phosphonate groups at C-17 were successfully synthesized.
- The reaction was optimized under solvent-free conditions using a large excess of dialkyl phosphite.
- Methylation of lactam NH was observed when using dimethyl phosphite.
Conclusions:
- The developed method provides access to novel phosphonate-containing steroids.
- These compounds represent potential leads for 5 alpha-reductase inhibitor drug discovery.
- The reaction conditions also facilitate unexpected modifications like lactam NH methylation.