Efficient N-acyldopamine synthesis

Yotaro Matsumoto, Akihiro Ito, Motonari Uesugi, Atsushi Kittaka

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

N-Acyldopamines are endogenous analogs of capsaicin that exhibit cannabinoid-like activities and were identified from brain extracts. Among them, N-arachidonoyldopamine (AADA) and N-oleoyldopamine (ODA) were characterized as transient receptor potential vanilloid type V1 channel (TRPV1) ligands. Recently, it was shown that N-acyldopamines may possess diverse physiological roles in addition to their ligand activities. To study the multiple functions and action mechanisms of endogenous N-acyldopamines, a simple and efficient method of N-acyldopamine synthesis was investigated. The eighteen potentially endogenous N-acyl-dopamines and two deuterated ones, N-palmitoyl dopamine-d5 and N-stearoyl dopamine-d5, were efficiently synthesized without protective groups in CH2Cl2 under optimized conditions using propylphosphoric acid cyclic anhydride (PPACA) as a condensation agent.

Original languageEnglish
Pages (from-to)935-940
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume64
Issue number7
DOIs
Publication statusPublished - 2016 Jan 1

Keywords

  • Amide bond formation
  • Cannabinoid type 1 receptor
  • Endocannabinoid
  • N-acyldopamine
  • Transient receptor potentioal vanilloid type 1 channel

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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