Investigation of 1,4-Substituted 1,2,3-Triazole Derivatives as Antiarrhythmics: Synthesis, Structure, and Properties

Here, we investigated the reaction of 1,3-dipolar cycloaddition of 1,3-diazido-2-nitro-2- azapropane (DANP) to propargyl alcohol over a copper-based catalyst and identified the optimum reaction conditions that enable the synthesis of 2-nitro-1,3-bis(4,4′-dihydroxymethyl)-1,2,3-triazolyl-2-azapropane...

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Bibliographic Details
Main Authors: Elena O. Shestakova, Sergey G. Il’yasov, Irina A. Shchurova, Vera S. Glukhacheva, Dmitri S. Il’yasov, Egor E. Zhukov, Arkady O. Bryzgalov, Tatiana G. Tolstikova, Yuri V. Gatilov
Format: Article
Language:English
Published: MDPI AG 2022-11-01
Series:Pharmaceuticals
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Online Access:https://www.mdpi.com/1424-8247/15/12/1443
Description
Summary:Here, we investigated the reaction of 1,3-dipolar cycloaddition of 1,3-diazido-2-nitro-2- azapropane (DANP) to propargyl alcohol over a copper-based catalyst and identified the optimum reaction conditions that enable the synthesis of 2-nitro-1,3-bis(4,4′-dihydroxymethyl)-1,2,3-triazolyl-2-azapropane (<b>1</b>) in more than 84% yield. The reaction between DANP, 1,5-diazido-3-nitrazapentane, and phenylacetylene produced the respective 1,2,3-triazole derivatives in 83% and 71% yields, respectively. The structures of the resultant compounds were validated by infrared and NMR spectroscopies and elemental analysis. The structure of <b>1</b> was proved by single-crystal X-ray diffraction. This study demonstrated that <b>1</b> exhibits a dose-dependent antiarrhythmic activity towards calcium-chloride-induced arrhythmia and refers to Class III: moderately hazardous substances.
ISSN:1424-8247