Synthesis and X-ray structural studies of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-а]pyrimidine L-arginine and piperidine salts

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2019-10, Vol.55 (10), p.989-992
• Main Authors: Slepukhin, Pavel А., Voinkov, Egor K., Ulomskiy, Eugeny N., Savateev, Konstantin V., Kopchuk, Dmitry S., Zyryanov, Grigory V., Fedotov, Victor V., Charushin, Valery N., Chupakhin, Oleg N., Rusinov, Vladimir L.
• Format: Article
• Language: English
• Subjects: Antiviral agents; Arginine; Biological effects; Chemistry; Chemistry and Materials Science; Comparative analysis; Crystal structure; Crystals; Hydrogen; Hydrogen bonding; Hydrogen bonds; Organic Chemistry; Pharmacy; Piperidine; Pyrimidines; Structural analysis; Structure
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-019-02567-6

The previously described L-argininium 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5- a ]pyrimidinide monohydrate and piperidinium 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5- a ]pyrimidinide, which has not been described previously, were synthesized as promising antiviral drugs. A detailed comparison of the crystal structures of these two compounds was performed. It is shown that the replacement of the L-arginine cation with piperidinium one leads to a serious reorganization of the system of intermolecular hydrogen bonds in the solid state, which, in our opinion, can have a significant impact on the interaction of the new drug with biological targets. Thus, by comparing the X-ray structural analysis data, the probability of the influence of the nature of the counterion on the biological effect of the drug was demonstrated.