期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 27, 期 38, 页码 9774-9781出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202101391
关键词
bioactivity; cycloisomerization; heterocycles; iodination; multicomponent reactions; Toxoplasma gondii
资金
- Deutsche Forschungsgemeinschaft [GRK2158, Mu1088/9-1]
- Fonds der Chemischen Industrie
- Projekt DEAL
A gold-catalyzed cycloisomerization reaction was used to synthesize a series of luminescent silylated heterocycles, whose optical properties can be tuned by different functional groups. These compounds also showed promising anti-parasitic activities, making them potential candidates for novel anti-parasitic therapies.
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 sigma(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 mu M. Thus, these compounds are promising candidates for novel anti-parasitic therapies.
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