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 / C. Marucci, M.S. Christodoulou, S. Pieraccini, M. Sironi, F. Dapiaggi, D. Cartelli, A.M. Calogero, G. Cappelletti, C. Vilanova, S. Gazzola, G. Broggini, D. Passarella. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2016:11(2016), pp. 2029-2036. [10.1002/ejoc.201600130]

Synthesis of Pironetin-Dumetorine Hybrids as Tubulin Binders

C. Marucci;M.S. Christodoulou;S. Pieraccini;M. Sironi;F. Dapiaggi;D. Cartelli;A.M. Calogero;G. Cappelletti;D. Passarella
2016

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.
alkaloids; allylation; drug design; hydrogen bonds; natural products; tubulin binders; organic chemistry; physical and theoretical chemistry
Settore CHIM/06 - Chimica Organica
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/437334
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