Synthesis of Pironetin-Dumetorine Hybrids as Tubulin Binders
| Autor: | Gianluigi Broggini, Cristina Marucci, Maurizio Sironi, Daniele Cartelli, Daniele Passarella, Graziella Cappelletti, Stefano Pieraccini, Silvia Gazzola, Concepción Vilanova, Michael S. Christodoulou, Alessandra Maria Calogero, Federico Dapiaggi |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Natural products
biology Allylation 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Tubulin binders 010402 general chemistry 01 natural sciences Combinatorial chemistry Drug design 0104 chemical sciences Hydrogen bonds Tubulin Alkaloids Docking (molecular) Dumetorine biology.protein Physical and Theoretical Chemistry |
| Popis: | The synthesis of the eight stereoisomers of 6-[2-methoxy-3-(piperidinyl)propyl]-5,6-dihydropyran-2-one is reported. The configuration at C2′ and C6 is induced by a sterecontrolled allylation reaction with DIP-Cl. The general structure is the result of merging the structures of two natural products (pironetin and dumetorine) with the aim of discovering a new scaffold for tubulin binders. Docking studies and biological evaluations confirm the validity of the approach. |
| Databáze: | OpenAIRE |
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