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

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-(1,2,3-1 -triazol-1-yl)cinnolines. The synthetic route is based on the Ric...

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Bibliographic Details
Published in:	Molecules (Basel, Switzerland) Vol. 24; no. 13; p. 2386
Main Authors:	Danilkina, Natalia A, Bukhtiiarova, Nina S, Govdi, Anastasia I, Vasileva, Anna A, Rumyantsev, Andrey M, Volkov, Artemii A, Sharaev, Nikita I, Povolotskiy, Alexey V, Boyarskaya, Irina A, Kornyakov, Ilya V, Tokareva, Polina V, Balova, Irina A
Format:	Journal Article
Language:	English
Published:	Switzerland MDPI AG 27-06-2019 MDPI
Subjects:	Alkynes Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Aromatic compounds Azide azides Bromine Cell Survival - drug effects Chemical reactions cinnolines Click Chemistry CuAAC cycloalkynes Cytotoxicity Decomposition Electron transfer Fluorescence Functional groups HeLa Cells Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Heterocyclic Compounds, 2-Ring - pharmacology Humans Ligands Molecular Structure Planar structures Reaction products Richter cyclization Sodium Substitution reactions Suzuki coupling Triazoles Triazoles - chemical synthesis Triazoles - chemistry Triazoles - pharmacology Suzuki coupling cinnolines Richter cyclization cycloalkynes fluorescence CuAAC alkynes triazoles azides cytotoxicity
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Summary:	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-(1,2,3-1 -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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules24132386