Synthesis of Pironetin-Dumetorine Hybrids as Tubulin Binders

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 (...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-04, Vol.2016 (11), p.2029-2036
Main Authors: 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
Format: Article
Language:English
Subjects:
Alkaloids
Allylation
Drug design
Hydrogen bonds
Natural products
Tubulin binders
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Summary: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. The synthesis of eight stereoisomers of 6‐[2‐methoxy‐3‐(piperidinyl)propyl]‐5,6‐dihydropyran‐2‐one, a pironetin–dumetorine hybrid scaffold is reported. 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 binding agents.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600130