Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/6499
Title: Synthesis of 5,6-dihydro-4H-benzo[d]isoxazol-7-one and 5,6-dihydro-4H-isoxazolo[5,4-c]pyridin-7-one Derivatives as Potential Hsp90 Inhibitors
Authors: Musso, Loana
Cincinelli, Raffaella
Giannini, Giuseppe
Manetti, Fabrizio 
Dallavalle, Sabrina
Keywords: Hsp90 inhibitors; anticancer; docking calculations; isoxazoles; synthesis
Issue Date: 2015
Project: None 
Journal: CHEMICAL BIOLOGY & DRUG DESIGN
Abstract: 
A novel class of 5,6-dihydro-4H-benzo[d]isoxazol-7-ones and 5,6-dihydro-4H-isoxazolo[5,4-c]pyridin-7-ones was designed, synthesized, and assayed to investigate the affinity toward Hsp90 protein. The synthetic route was based on a 1,3-dipolar cycloaddition of nitriloxides, generated in situ from suitable benzaldoximes, with 2-bromocyclohex-2-enones or 3-bromo-5,6-dihydro-1H-pyridin-2-ones. Whereas all the compounds bearing a benzamide group on the bicyclic scaffold were devoid of activity, the derivatives carrying a resorcinol-like fragment showed a remarkable inhibitory effect on Hsp90. Docking calculations were performed to investigate the orientation of the new compounds within the binding site of the enzyme.
Description: 
206983
URI: http://hdl.handle.net/20.500.12779/6499
ISSN: 1747-0277
DOI: 10.1111/cbdd.12570
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