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Synthesis of tetrapyridoporphyrazines with potential photodynamic activity
Vavrečková, Magda ; Zimčík, Petr (advisor) ; Kučerová, Marta (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Drug Control Candidate Magda Vavrečková Supervisor Doc. PharmDr. Petr Zimčík, Ph.D. Title of Thesis Synthesis of tetrapyridoporphyrazines with potential photodynamic activity Substituted tetrapyridoporphyrazines represent new structural type of potential photosensitizers with interesting properties for application in photodynamic therapy. The aim of this work was to synthesize two types of tetrapyridoporphyrazines with hydrophilic substituents as potential photosensitizers. Photosensitizers are substances with an ability to produce singlet oxygen after activation by light. Singlet oxygen is the key toxic species in photodynamic therapy. 2-Chloro-5,6-dimethylpyridine-3,4-dicarbonitrile (1) was prepared in the first step by condensation of tetracyanoethylene and butan-2-one. In the next step, a hydrophilic substituent was attached by nucleophilic substitution. The first precursor was prepared by reaction of compound 1 with 2-mercaptoethanol in the presence of sodium hydroxide. Similarly, the second precursor was obtained by reaction of compound 1 with diethylaminoethanol in the presence of sodium hydride. The third step involved cyclotetramerization with magnesium butoxide as...
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Synthesis of tetrapyridoporphyrazines with potential photodynamic activity
Vavrečková, Magda ; Zimčík, Petr (advisor) ; Kučerová, Marta (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Drug Control Candidate Magda Vavrečková Supervisor Doc. PharmDr. Petr Zimčík, Ph.D. Title of Thesis Synthesis of tetrapyridoporphyrazines with potential photodynamic activity Substituted tetrapyridoporphyrazines represent new structural type of potential photosensitizers with interesting properties for application in photodynamic therapy. The aim of this work was to synthesize two types of tetrapyridoporphyrazines with hydrophilic substituents as potential photosensitizers. Photosensitizers are substances with an ability to produce singlet oxygen after activation by light. Singlet oxygen is the key toxic species in photodynamic therapy. 2-Chloro-5,6-dimethylpyridine-3,4-dicarbonitrile (1) was prepared in the first step by condensation of tetracyanoethylene and butan-2-one. In the next step, a hydrophilic substituent was attached by nucleophilic substitution. The first precursor was prepared by reaction of compound 1 with 2-mercaptoethanol in the presence of sodium hydroxide. Similarly, the second precursor was obtained by reaction of compound 1 with diethylaminoethanol in the presence of sodium hydride. The third step involved cyclotetramerization with magnesium butoxide as...
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Synthesis of tetrapyridoporphyrazines with potential photodynamic activity
Vavrečková, Magda ; Zimčík, Petr (advisor) ; Kučerová, Marta (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Drug Control Candidate Magda Vavrečková Supervisor Doc. PharmDr. Petr Zimčík, Ph.D. Title of Thesis Synthesis of tetrapyridoporphyrazines with potential photodynamic activity Substituted tetrapyridoporphyrazines represent new structural type of potential photosensitizers with interesting properties for application in photodynamic therapy. The aim of this work was to synthesize two types of tetrapyridoporphyrazines with hydrophilic substituents as potential photosensitizers. Photosensitizers are substances with an ability to produce singlet oxygen after activation by light. Singlet oxygen is the key toxic species in photodynamic therapy. 2-Chloro-5,6-dimethylpyridine-3,4-dicarbonitrile (1) was prepared in the first step by condensation of tetracyanoethylene and butan-2-one. In the next step, a hydrophilic substituent was attached by nucleophilic substitution. The first precursor was prepared by reaction of compound 1 with 2-mercaptoethanol in the presence of sodium hydroxide. Similarly, the second precursor was obtained by reaction of compound 1 with diethylaminoethanol in the presence of sodium hydride. The third step involved cyclotetramerization with magnesium butoxide as...
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