Indole-based melatonin analogues: Synthetic approaches and biological activity

Eur J Med Chem. 2020 Jan 1:185:111847. doi: 10.1016/j.ejmech.2019.111847. Epub 2019 Nov 5.

Abstract

Melatonin is a natural hormone primarily released by the pineal gland that regulates the sleep-wake cycles. The diverse biological applications of melatonin, together with the need to develop new melatoninergic ligands, have stimulated the preparation of a wide range of melatonin derivatives. Here, all the synthetic approaches to indole-based melatonin analogues as well as their biological applications are reviewed. The modifications which have been performed on the melatonin's indole ring and the effects of these modifications on the biological activities have been analysed, detailing the binding affinity of the derivatives for melatonin receptors.

Keywords: Chemical synthesis; Derivatization; Melatonin analogues; Melatonin receptors; Melatoninergic ligands.

Publication types

  • Review

MeSH terms

  • Animals
  • Dose-Response Relationship, Drug
  • Humans
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Ligands
  • Melatonin / analogs & derivatives
  • Melatonin / chemistry
  • Melatonin / pharmacology*
  • Molecular Structure
  • Receptors, Melatonin / agonists*
  • Structure-Activity Relationship

Substances

  • Indoles
  • Ligands
  • Receptors, Melatonin
  • Melatonin