Antiviral drug Triazavirin, selectively labeled with 2H, 13C, and 15N stable isotopes. Synthesis and properties

Tatyana S Shestakova; Sergey L Deev; Igor А Khalymbadzha; Vladimir L Rusinov; Alexander S Paramonov; Alexander S Arseniev; Zakhar O Shenkarev; Valery N Charushin; Oleg N Chupakhin

doi:10.1007/s10593-021-02927-1

Antiviral drug Triazavirin, selectively labeled with ²H, ¹³C, and ¹⁵N stable isotopes. Synthesis and properties

Chem Heterocycl Compd (N Y). 2021;57(4):479-482. doi: 10.1007/s10593-021-02927-1. Epub 2021 May 12.

Authors

Affiliations

¹ Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002 Russia.
² Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg, 620108 Russia.
³ Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997 Russia.

Abstract

Isotope-labeled antiviral drug Triazavirin containing ²H, ¹³C, and ¹⁵N atoms in its structure has been synthesized. ¹³C²H₃I and KS¹³CN served as donors of ¹³C isotopes. The use of ¹³С-MeI containing ²H atoms made it possible to additionally incorporate deuterium labels into the structure of the compound. The ¹⁵N atoms were incorporated using ¹⁵N-enriched sodium nitrite, aminoguanidine carbonate, and ethyl nitroacetate. The resulting ²H₃,¹³C₂,¹⁵N₃-Triazavirin was characterized by NMR spectroscopy.

Supplementary information: The online version contains supplementary material available at 10.1007/s10593-021-02927-1.

Keywords: NMR spectroscopy; antiviral activity; azoloazines; spin-spin coupling constants; stable isotopes.