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A synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones and investigation of their chemical and cytotoxic properties. / Lyapustin, Daniil; Fayzullina, Dilya; Marusich, Irina et al.
In: Chemistry of Heterocyclic Compounds, Vol. 60, No. 1-2, 01.02.2024, p. 52-57.

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@article{470abd3b3b1a41abbf17b50a07732fe5,
title = "A synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones and investigation of their chemical and cytotoxic properties",
abstract = "A method for the synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones by heterocyclization of 3-aminoazoles and 5-[bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones was developed. 5-Methylsulfanyl-7-oxo-4,7-dihydroazolo- [1,5-a]pyrimidine-6-carboxylic acid was isolated during optimization of the process, which allowed us to establish the sequence of transformations of this heterocyclization reaction. The reactivity of the resulting 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones in classical electrophilic substitution reactions was studied. The cytotoxic effect of these compounds toward A549, HepG2, and RD tumor cell lines as well as normal HEK-293 cells was assessed.",
author = "Daniil Lyapustin and Dilya Fayzullina and Irina Marusich and Svetlana Kotovskaya and Vsevolod Melekhin and Maria Tokhtueva and Evgeny Ulomsky and Vladimir Rusinov",
note = "The study was carried out with financial support from the Ministry of Science and Higher Education of the Russian Federation within the framework of the Development Program of the Ural Federal University named after the first President of Russia B. N. Yeltsin in accordance with the strategic academic leadership program \u201CPriority-2030\u201D.",
year = "2024",
month = feb,
day = "1",
doi = "10.1007/s10593-024-03293-4",
language = "English",
volume = "60",
pages = "52--57",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer Verlag",
number = "1-2",

}

RIS

TY - JOUR

T1 - A synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones and investigation of their chemical and cytotoxic properties

AU - Lyapustin, Daniil

AU - Fayzullina, Dilya

AU - Marusich, Irina

AU - Kotovskaya, Svetlana

AU - Melekhin, Vsevolod

AU - Tokhtueva, Maria

AU - Ulomsky, Evgeny

AU - Rusinov, Vladimir

N1 - The study was carried out with financial support from the Ministry of Science and Higher Education of the Russian Federation within the framework of the Development Program of the Ural Federal University named after the first President of Russia B. N. Yeltsin in accordance with the strategic academic leadership program \u201CPriority-2030\u201D.

PY - 2024/2/1

Y1 - 2024/2/1

N2 - A method for the synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones by heterocyclization of 3-aminoazoles and 5-[bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones was developed. 5-Methylsulfanyl-7-oxo-4,7-dihydroazolo- [1,5-a]pyrimidine-6-carboxylic acid was isolated during optimization of the process, which allowed us to establish the sequence of transformations of this heterocyclization reaction. The reactivity of the resulting 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones in classical electrophilic substitution reactions was studied. The cytotoxic effect of these compounds toward A549, HepG2, and RD tumor cell lines as well as normal HEK-293 cells was assessed.

AB - A method for the synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones by heterocyclization of 3-aminoazoles and 5-[bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones was developed. 5-Methylsulfanyl-7-oxo-4,7-dihydroazolo- [1,5-a]pyrimidine-6-carboxylic acid was isolated during optimization of the process, which allowed us to establish the sequence of transformations of this heterocyclization reaction. The reactivity of the resulting 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones in classical electrophilic substitution reactions was studied. The cytotoxic effect of these compounds toward A549, HepG2, and RD tumor cell lines as well as normal HEK-293 cells was assessed.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85189480713

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001197867500002

U2 - 10.1007/s10593-024-03293-4

DO - 10.1007/s10593-024-03293-4

M3 - Article

VL - 60

SP - 52

EP - 57

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 1-2

ER -

ID: 56632319