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

Pei Wen Wu, Yi Ming Cheng, Wan Ting Hsieh, Yu Hsiu Wang, Ching Yen Wei, Pi Tai Chou

Research output: Contribution to journalArticle

9 Scopus citations

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 ∼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.

Original languageEnglish (US)
Pages (from-to)1071-1075
Number of pages5
JournalChemMedChem
Volume2
Issue number7
DOIs
StatePublished - Jul 9 2007
Externally publishedYes

Keywords

  • 7-azamelatonin
  • DFT
  • Docking
  • Excited-state double proton transfer (ESDPT)

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Drug Discovery
  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

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