Synthesis of steroidal 1,2- and 1,3-diamines as ligands for transition metal ion complexation
| Autor: | Agnieszka Hryniewicka, Barbara Seroka, Ewelina Dudź, Przemysław Bazydło, Agnieszka Wojtkielewicz, Jacek W. Morzycki, Zenon Łotowski |
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| Rok vydání: | 2019 |
| Předmět: |
Ions
Pharmacology Bromoacetonitrile Substitution reaction Molecular Structure Chemistry Mesylate Organic Chemistry Clinical Biochemistry 030209 endocrinology & metabolism Diamines Ligands Biochemistry Combinatorial chemistry Transition metal ions 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Endocrinology Coordination Complexes 030220 oncology & carcinogenesis Transition Elements Cholestane Acrylonitrile Molecular Biology |
| Zdroj: | Steroids. 147:19-27 |
| ISSN: | 0039-128X |
| DOI: | 10.1016/j.steroids.2019.02.001 |
| Popis: | Two series of cholestane-based diamines (1,2 and 1,3) were synthesized using simple and efficient procedures. The convenient substrates for these syntheses were cholesteryl mesylate and tosylate, which were converted to appropriate amines via easily obtained azides. The final diamines were prepared using a substitution reaction with bromoacetonitrile (in the case of 1,2-diamines) or condensation with acrylonitrile (in the case of 1,3-diamines), followed by the reduction of intermediate aminonitriles. Furthermore, the other two amines were synthesized from 16-dehydropregnenolone acetate using aza-Michael addition as a key step. Some of the diamines were subjected to complexation reactions with K2PtCl4 to form steroidal analogs of cisplatin. The synthetic methods tested in this work will allow us to prepare other cisplatin derivatives based on steroids showing anticancer properties themselves. |
| Databáze: | OpenAIRE |
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