7-Azamelatonin: efficient synthetic routes, excited-state double proton transfer properties and biomedical implications

ChemMedChem. 2007 Jul;2(7):1071-5. doi: 10.1002/cmdc.200700043.

Abstract

On the basis of a seven-step synthetic route, the total synthesis of 7-azamelatonin, an analogue of melatonin, has been achieved with an overall yield of approximately 9.2%. In aqueous solution, 7-azamelatonin exhibits a unique excited-state double proton transfer (ESDPT) property, resulting in dual emission bands (405 and 560 nm). The ESDPT property makes 7-azamelatonin superb as a potential molecular probe for future bioapplication and for pharmacological research.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Melatonin / analogs & derivatives*
  • Melatonin / chemical synthesis
  • Melatonin / chemistry
  • Melatonin / pharmacology
  • Protons
  • Spectrometry, Mass, Electrospray Ionization
  • Spectroscopy, Fourier Transform Infrared

Substances

  • 7-azamelatonin
  • Protons
  • Melatonin