Abstract

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.

Original languageEnglish
JournalMolecules
Volume24
Issue number13
DOIs
Publication statusPublished - 27 Jun 2019

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Triazoles
alkynes
Alkynes
fluorescence
Functional groups
rings
Bearings (structural)
synthesis
bromine
Fluorescence
reaction products
Bromine
electron transfer
Azides
Cyclization
quenching
routes
substitutes
Reaction products
HeLa Cells

Cite this

@article{4cca3cbc83af41abb81217c32bde7c2a,
title = "Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines",
abstract = "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.",
author = "Danilkina, {Natalia A.} and Bukhtiiarova, {Nina S.} and Govdi, {Anastasia I.} and Vasileva, {Anna A.} and Rumyantsev, {Andrey M.} and Volkov, {Artemii A.} and Sharaev, {Nikita I.} and Povolotskiy, {Alexey V.} and Boyarskaya, {Irina A.} and Kornyakov, {Ilya V.} and Tokareva, {Polina V.} and Balova, {Irina A.}",
year = "2019",
month = "6",
day = "27",
doi = "10.3390/molecules24132386",
language = "English",
volume = "24",
journal = "Molecules",
issn = "1420-3049",
publisher = "MDPI AG",
number = "13",

}

TY - JOUR

T1 - Synthesis and Properties of 6-Aryl-4-azidocinnolines and 6-Aryl-4-(1,2,3-1H-triazol-1-yl)cinnolines

AU - Danilkina, Natalia A.

AU - Bukhtiiarova, Nina S.

AU - Govdi , Anastasia I.

AU - Vasileva, Anna A.

AU - Rumyantsev, Andrey M.

AU - Volkov, Artemii A.

AU - Sharaev, Nikita I.

AU - Povolotskiy, Alexey V.

AU - Boyarskaya, Irina A.

AU - Kornyakov, Ilya V.

AU - Tokareva, Polina V.

AU - Balova, Irina A.

PY - 2019/6/27

Y1 - 2019/6/27

N2 - 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.

AB - 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.

UR - https://www.mdpi.com/1420-3049/24/13/2386

UR - http://www.mendeley.com/research/synthesis-properties-6aryl4azidocinnolines-6aryl41231htriazol1ylcinnolines

U2 - 10.3390/molecules24132386

DO - 10.3390/molecules24132386

M3 - Article

VL - 24

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 13

ER -