David Šarlah (Author), Amadej Juranovič (Author), Boris Kožar (Author), Luka Rejc (Author), Amalija Golobič (Author), Andrej Petrič (Author)

Abstract

Naphthalene derivatives bearing electron-accepting and electron-donating groups at the 2,6-positions belong to the family of D-π-A push-pull dyes. It has been found that these compounds, e.g., 2-(1-(6-((2-(fluoro)ethyl)(methyl)amino)naphthalen-2-yl)ethylidene)malononitrile (FDDNP), show not only interesting optical properties, such as solvatochromism, but they have the potential to label protein aggregates of different compositions formed in the brain of patients suffering from neurodegenerative diseases like Alzheimer’s (AD). In continuation of our research we set our goal to find new FDDNP analogs, which would inherit optical and binding properties but hopefully show better specificity for tau protein aggregates, which are characteristic for neurodegeneration caused by repetitive mild trauma. In this work we report on the synthesis of new FDDNP analogs in which the acceptor group has been formally replaced with an aromatic five- or six-membered heterocycle. The heterocyclic moiety was annealed to the central naphthalene ring either by classical ring closure reactions or by modern transition metal-catalyzed coupling reactions. The chemical characterization, NMR spectra, and UV/vis properties of all new compounds are reported.

Keywords

organska kemija;analogi FDDNP;push-pull barvila;heterociklizacije;cross-coupling reakcije;UV/vis spektroskopija;FDDNP analogs;push-pull dyes;heterocyclization;cross-coupling reactions;UV/vis spectroscopy;

Data

Language: English
Year of publishing:
Typology: 1.01 - Original Scientific Article
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
UDC: 547.65.057
COBISS: 1536799939 Link will open in a new window
ISSN: 1420-3049
Views: 177
Downloads: 52
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Other data

Secondary language: Slovenian
Secondary keywords: organska kemija;analogi FDDNP;push-pull barvila;heterociklizacije;cross-coupling reakcije;UV/vis spektroskopija;
Type (COBISS): Article
Pages: str. 1-16
Volume: ǂVol. ǂ21
Issue: ǂiss. ǂ3
Chronology: 2016
DOI: 10.3390/molecules21030267
ID: 13394689