Direct amidation to access 3-Amido-1,8-Naphthalimides including fluorescent scriptaid analogues as HDAC inhibitors
Publication Year 2021-06-15, Volume 10, Issue #6, Page 1505
Journal Title
Methodology to access fluorescent 3-amido-1,8-naphthalimides using direct Buchwald-Hartwig amidation is described. The protocol was successfully used to couple a number of substrates (including an alkylamide, an arylamide, a lactam and a carbamate) to 3-bromo-1,8-naphthalimide in good yield. To further exemplify the approach, a set of scriptaid analogues with amide substituents at the 3-position were prepared. The new compounds were more potent than scriptaid at a number of histone deacetylase (HDAC) isoforms including HDAC6. Activity was further confirmed in a whole cell tubulin deacetylation assay where the inhibitors were more active than the established HDAC6 selective inhibitor Tubastatin. The optical properties of these new, highly active, compounds make them amenable to cellular imaging studies and theranostic applications.
1,8-naphthalimide; Buchwald–Hartwig; Hdac; fluorescence; histone deacetylase; imaging; scriptaid; tubulin deacetylase
WEHI Research Division(s)
Chemical Biology
PubMed ID
Open Access at Publisher's Site
Rights Notice
Refer to copyright notice on published article.

Creation Date: 2021-07-20 11:18:06
Last Modified: 2021-07-20 12:04:42
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