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Keywords = azidoalkyl nitramines

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15 pages, 2587 KiB  
Article
Investigation of 1,4-Substituted 1,2,3-Triazole Derivatives as Antiarrhythmics: Synthesis, Structure, and Properties
by 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 and Yuri V. Gatilov
Pharmaceuticals 2022, 15(12), 1443; https://doi.org/10.3390/ph15121443 - 22 Nov 2022
Cited by 4 | Viewed by 2496
Abstract
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 (1) in more than 84% yield. The reaction between DANP, [...] Read more.
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 (1) 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 1 was proved by single-crystal X-ray diffraction. This study demonstrated that 1 exhibits a dose-dependent antiarrhythmic activity towards calcium-chloride-induced arrhythmia and refers to Class III: moderately hazardous substances. Full article
(This article belongs to the Special Issue Nitro Group Containing Drugs)
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