Fluorescent Indolo[3,2‐ a ]phenazines against Toxoplasma gondii : Concise Synthesis by Gold‐Catalyzed Cycloisomerization with 1,2‐Silyl Migration and ipso ‐Iodination Suzuki Sequence
| Autor: | Klaus Pfeffer, Irina Gruber, Shabnam Shaneh Sazzadeh, Christoph Janiak, Flaminia Mazzone, Thomas Müller, Karin Buchholz, Larissa K. E. Hinz, Franziska K. Merkt, Lorand Bonda |
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| Rok vydání: | 2021 |
| Předmět: |
Silylation
Trimethylsilyl 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Substituent Halogenation General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound Cycloisomerization Suzuki reaction Yield (chemistry) Luminophore |
| Zdroj: | Chemistry – A European Journal. 27:9774 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202101391 |
| Popis: | A gold‐catalyzed cycloisomerization of 2‐indolyl‐3‐[(trimethylsilyl)ethynyl)]quinoxalines with concomitant 1,2‐silyl shift forms 6‐(trimethylsilyl)indolo[3,2‐a]phenazines in moderate to excellent yield. These silylated heterocycles are readily transformed into 6‐aryl‐indolo[3,2‐a]phenazines in moderate to good yield by one‐pot ipso‐iodination Suzuki coupling. The title compounds represent a novel type of tunable luminophore. Structure‐property relationships for 6‐aryl‐indolo[3,2‐a]phenazines obtained from Hammett correlations with σ p+ substituent parameters indicate that emission maxima, Stokes shifts, and fluorescence quantum yields can be fine‐tuned by the remote para‐aryl substituent. Furthermore, indolo[3,2‐a]phenazines were found to exhibit interesting activities against medically relevant pathogens such as the Apicomplexa parasite Toxoplasma gondii with an IC50 of up to 0.67±0.13 μM. Thus, these compounds are promising candidates for novel anti‐parasitic therapies. |
| Databáze: | OpenAIRE |
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