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.

Synthesis of Pironetin-Dumetorine Hybrids as Tubulin Binders

GAZZOLA, SILVIA;BROGGINI, GIANLUIGI;
2016-01-01

Abstract

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.
2016
www.interscience.wiley.com
Alkaloids; Allylation; Drug design; Hydrogen bonds; Natural products; Tubulin binders; Organic Chemistry; Physical and Theoretical Chemistry
Marucci, Cristina; Christodoulou, Michael S.; Pieraccini, Stefano; Sironi, Maurizio; Dapiaggi, Federico; Cartelli, Daniele; Calogero, Alessandra M.; Cappelletti, Graziella; Vilanova, Concepción; Gazzola, Silvia; Broggini, Gianluigi; Passarella, Daniele
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2051995
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