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

A method for the synthesis of novel 5-methylsulfanylazolo[1,5- a ]pyrimidin-7(4 H )-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...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2024-02, Vol.60 (1-2), p.52-57
Main Authors: Lyapustin, Daniil N., Fayzullina, Dilya F., Marusich, Irina V., Kotovskaya, Svetlana K., Melekhin, Vsevolod V., Tokhtueva, Maria D., Ulomsky, Evgeny N., Rusinov, Vladimir L.
Format: Article
Language:English
Subjects:
Carboxylic acids
Chemistry
Chemistry and Materials Science
Diketones
Organic Chemistry
Pharmacy
Substitution reactions
Synthesis
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A method for the synthesis of novel 5-methylsulfanylazolo[1,5- a ]pyrimidin-7(4 H )-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(4 H )-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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-024-03293-4