Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity

Vladimir V. Chernyshov, Olga I. Yarovaya, Dmitry S. Fadeev, Yuriy V. Gatilov, Yana L. Esaulkova, Anna S. Muryleva, Katherina O. Sinegubova, Vladimir V. Zarubaev, Nariman F. Salakhutdinov

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

An effective technique for one-stage synthesis of new polycyclic nitrogen-containing compounds has been developed. The procedure involves refluxing mixtures of camphoric acid with aliphatic or aromatic diamine without catalysts. In cases where the starting amine has a low boiling point (less than 200 °C), phenol is used as a solvent, as it is the most optimal one for obtaining products with good yields. It has been shown that the use of Lewis acids as catalysts reduces the yield of the reaction products. A set of compounds have been synthesized, which can be attributed to synthetic analogues of alkaloids. In vitro screening for activity influenza virus A was carried out for the obtained compounds. The synthesized quinazoline-like agent 14 has inhibitory activity against different strains of influenza viruses.

Original languageEnglish
Pages (from-to)61-67
Number of pages7
JournalMolecular Diversity
Volume24
Issue number1
DOIs
Publication statusPublished - 1 Feb 2020

Keywords

  • (+)-Camphoric acid
  • Alkaloid analogues
  • Antiviral activity
  • Antivirals
  • Influenza virus
  • Single-stage synthesis
  • ARBIDOL
  • INHIBITION
  • INFLUENZA-A VIRUS
  • LIGANDS
  • DIETHYLZINC
  • CHEMISTRY
  • RESISTANCE
  • DERIVATIVES
  • VASICINE

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