Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines

Molecules

ArtemiiA. Volkov¹  NikitaI. Sharaev¹  AndreyM. Rumyantsev¹  IrinaA. Balova²  AnastasiaI. Govdi²  IrinaA. Boyarskaya²  NinaS. Bukhtiiarova²  PolinaV. Tokareva²  NataliaA. Danilkina²  AnnaA. Vasileva²  IlyaV. Kornyakov²  AlexeyV. Povolotskiy² 

[1] Department of Genetics and Biotechnology, Saint Petersburg State University (SPSU), Universitetskaya nab. 7/9, Saint Petersburg 199034, Russia;Institute of Chemistry, Saint Petersburg State University (SPSU), Universitetskaya nab. 7/9, Saint Petersburg 199034, Russia;

关键词: azides;    cinnolines;    triazoles;    CuAAC;    alkynes;    cycloalkynes;    Richter cyclization;    Suzuki coupling;    fluorescence;    cytotoxicity;   

DOI  :  10.3390/molecules24132386

来源: DOAJ

【 摘 要 】

An efficient approach towards the synthesis of 6-aryl-4-azidocinnolines was developed with the aim of exploring the photophysical properties of 6-aryl-4-azidocinnolines and their click reaction products with alkynes, 6-aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines. The synthetic route is based on the Richter-type cyclization of 2-ethynyl-4-aryltriazenes with the formation of 4-bromo-6-arylcinnolines and nucleophilic substitution of a bromine atom with an azide functional group. The developed synthetic approach is tolerant to variations of functional groups on the aryl moiety. The resulting azidocinnolines were found to be reactive in both CuAAC with terminal alkynes and SPAAC with diazacyclononyne, yielding 4-triazolylcinnolines. It was found that 4-azido-6-arylcinnolines possess weak fluorescent properties, while conversion of the azido function into a triazole ring led to complete fluorescence quenching. The lack of fluorescence in triazoles could be explained by the non-planar structure of triazolylcinnolines and a possible photoinduced electron transfer (PET) mechanism. Among the series of 4-triazolylcinnoline derivatives a compound bearing hydroxyalkyl substituent at triazole ring was found to be cytotoxic to HeLa cells.

【 授权许可】

Unknown