Syntéza derivátů azaftalocyaninů s fenolickou skupinou jako fluorescenčních senzorů pro pH

• Main Author: Valer, Vojtěch
• Other Authors: Zimčík, Petr
• Format: Dissertation
• Language: Czech
• Published: 2017
• Online Access: http://www.nusl.cz/ntk/nusl-355841

Charles University, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Drug Control Candidate Vojtěch Valer Supervisor Doc. PharmDr. Petr Zimčík, Ph.D. Title of Thesis Synthesis of phenol-substituted azaphthalocyanines as fluorescent pH sensors Azaphtalocyanines (AzaPc) bearing suitable phenol moieties were found to be potentially useful pH sensors. In this study, we focused on expanding the series of phenol derivatives synthesized previously. The main reason of our effort was the fact, that pKa of the previous compounds (12.5-12.7) did not fall into physiologically useful range. Two different strategies to synthesis of precursors were developed. Synthesis of the precursor with two phenols started by benzoin condensation of p-anisaldehyde to obtain corresponding acyloin, which was oxidized to diketone and dealkylated. Subsequently, the substituted pyrazine was obtained by condensation of this diketone with diaminomaleonitrile (DAMN). Synthesis of precursor with one phenol began with oxidation of 4- hydroxyacetophenone to corresponding ketoaldehyde, which was used in condensation with DAMN to the pyrazine. The mixed cyclotetramerization of mono or disubstituted pyrazine with 5,6-bis(tert- butylsulfanyl)pyrazine-2,3-dicarbonitrile provided the mix of congeners...