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Direct amidation to access 3-Amido-1,8-naphthalimides including fluorescent scriptaid analogues as HDAC inhibitors


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Hearn, KN, Ashton, TD, Acharya, R, Feng, Z, Gueven, N ORCID: 0000-0003-3782-767X and Pfeffer, FM 2021 , 'Direct amidation to access 3-Amido-1,8-naphthalimides including fluorescent scriptaid analogues as HDAC inhibitors' , Cells, vol. 10 , pp. 1-10 , doi: 10.3390/cells10061505.

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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 ingood yield. To further exemplify the approach, a set of scriptaid analogues with amide substituentsat the 3-position were prepared. The new compounds were more potent than scriptaid at a numberof histone deacetylase (HDAC) isoforms including HDAC6. Activity was further confirmed in awhole cell tubulin deacetylation assay where the inhibitors were more active than the establishedHDAC6 selective inhibitor Tubastatin. The optical properties of these new, highly active, compoundsmake them amenable to cellular imaging studies and theranostic applications.

Item Type: Article
Authors/Creators:Hearn, KN and Ashton, TD and Acharya, R and Feng, Z and Gueven, N and Pfeffer, FM
Keywords: Buchwald–Hartwig, scriptaid, histone deacetylase, HDAC, 1,8-naphthalimide, fluorescence, imaging, tubulin deacetylase
Journal or Publication Title: Cells
Publisher: MDPI AG
ISSN: 2073-4409
DOI / ID Number: 10.3390/cells10061505
Copyright Information:

Copyright: © 2021 by the author. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution 4.0 International (CC BY 4.0) license (

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