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

1
Institute of Chemistry, Saint Petersburg State University (SPSU), Universitetskaya nab. 7/9, Saint Petersburg 199034, Russia
2
Department of Genetics and Biotechnology, Saint Petersburg State University (SPSU), Universitetskaya nab. 7/9, Saint Petersburg 199034, Russia
3
Laboratory of Nature-Inspired Technologies and Environmental Safety of the Arctic, Kola Science Centre, Russian Academy of Sciences, Fersmana 14, Apatity 184209, Russia
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(13), 2386; https://doi.org/10.3390/molecules24132386
Received: 11 June 2019 / Revised: 24 June 2019 / Accepted: 24 June 2019 / Published: 27 June 2019
(This article belongs to the Special Issue Modern Strategies for Heterocycle Synthesis)
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. View Full-Text
Keywords: azides; cinnolines; triazoles; CuAAC; alkynes; cycloalkynes; Richter cyclization; Suzuki coupling; fluorescence; cytotoxicity azides; cinnolines; triazoles; CuAAC; alkynes; cycloalkynes; Richter cyclization; Suzuki coupling; fluorescence; cytotoxicity
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Danilkina, N.A.; Bukhtiiarova, N.S.; Govdi, A.I.; Vasileva, A.A.; Rumyantsev, A.M.; Volkov, A.A.; Sharaev, N.I.; Povolotskiy, A.V.; Boyarskaya, I.A.; Kornyakov, I.V.; Tokareva, P.V.; Balova, I.A. Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines. Molecules 2019, 24, 2386.

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