title: Synthesis of Naphthalene-Based Push-Pull Molecules with a Heteroaromatic Electron Acceptor.
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.
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia. sarlah@illinois.edu.
authors.forename: David
authors.initials: D
authors.lastname: Šarlah
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia. amadej.juranovic@gmail.com.
authors.forename: Amadej
authors.initials: A
authors.lastname: Juranovič
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia. boris.kozar@hotmail.com.
authors.forename: Boris
authors.initials: B
authors.lastname: Kožar
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia. rejc.luka87@gmail.com.
authors.forename: Luka
authors.initials: L
authors.lastname: Rejc
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia. amalija.golobic@fkkt.uni-lj.si.
authors.forename: Amalija
authors.initials: A
authors.lastname: Golobič
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia. andrej.petric@fkkt.uni-lj.si.|EN-FIST Centre of Excellence, Trg Osvobodilne fronte 13, SI-1000 Ljubljana, Slovenia. andrej.petric@fkkt.uni-lj.si.
authors.forename: Andrej
authors.initials: A
authors.lastname: Petrič
mesh_terms: D016229:Amyloid beta-Peptides / Q000378:metabolism; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016875:tau Proteins / Q000378:metabolism
chemical_list: D016229:Amyloid beta-Peptides; D005456:Fluorescent Dyes; C054369:MAPT protein, human; D009281:Naphthalenes; D016875:tau Proteins
keywords: FDDNP analogs; UV/vis spectroscopy; cross-coupling reactions; heterocyclization; push-pull dyes