Derivatives of DANPY (Dialkylaminonaphthylpyridinium), a DNA-Binding Fluorophore: Practical Synthesis of Tricyclic 2-Amino-6-bromonaphthalenes by Bucherer Reaction

• Published in: ACS omega Vol. 5; no. 1; pp. 537 - 546
• Main Authors: Kingsbury, Jason S, Elder, Delwin L, Johnson, Lewis E, Smolarski, Brittany A, Zeitler, Hannah E, Armbruster, Emily G
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 14-01-2020
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.9b03107

A simple and convergent way to synthesize 2-amino-6-bromonaphthalenes involves condensation of free secondary amines with the corresponding 2-naphthol under Bucherer conditions. The amination protocol relies on common Teflon-capped pressure flasks and has been used to modify the tertiary aminonaphthalene core of DANPY, a biocompatible chromophore shown to be safe and effective for staining a variety of cellular targets. Following a Suzuki reaction with pyridine 4-boronic acid, additional diversity is introduced upon N-alkylation to install the pyridinium cation. New DANPY derivatives and intermediates reported herein reflect the modularity of the dye nucleus, including the addition of groups useful for applications in membrane staining and DNA-based biophotonics.