Fused 1,5-Naphthyridines: Synthetic Tools and Applications

Molecules. 2020 Jul 31;25(15):3508. doi: 10.3390/molecules25153508.

Abstract

Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in the fields of synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. In this review, a wide range of synthetic protocols for the construction of this scaffold are presented. For example, Friedländer, Skraup, Semmlere-Wolff, and hetero-Diels-Alder, among others, are well known classical synthetic protocols used for the construction of the main 1,5-naphthyridine scaffold. These syntheses are classified according to the nature of the cycle fused to the 1,5-naphthyridine ring: carbocycles, nitrogen heterocycles, oxygen heterocycles, and sulphur heterocycles. In addition, taking into account the aforementioned versatility of these heterocycles, their reactivity is presented as well as their use as a ligand for metal complexes formation. Finally, those fused 1,5-naphthyridines that present biological activity and optical applications, among others, are indicated.

Keywords: biological activity; fused 1,5-naphthyridines; heterocycle synthesis; metal complexes.

Publication types

  • Review

MeSH terms

  • Alkaloids / biosynthesis
  • Alkaloids / chemistry
  • Cell Survival / drug effects
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology
  • Cycloaddition Reaction
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacology
  • Humans
  • Naphthyridines / chemical synthesis
  • Naphthyridines / chemistry*
  • Naphthyridines / pharmacology
  • Oxidation-Reduction

Substances

  • Alkaloids
  • Coordination Complexes
  • Heterocyclic Compounds
  • Naphthyridines