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

Mol Divers. 2020 Feb;24(1):61-67. doi: 10.1007/s11030-019-09932-9. Epub 2019 Feb 28.

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.

Keywords: (+)-Camphoric acid; Alkaloid analogues; Antiviral activity; Antivirals; Influenza virus; Single-stage synthesis.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / pharmacology*
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Chemistry Techniques, Synthetic
  • Dose-Response Relationship, Drug
  • Influenza A Virus, H1N1 Subtype / drug effects
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Antiviral Agents