title: Efficient N-Acyldopamine Synthesis.
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-acyldopamines 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Teikyo University.
authors.forename: Yotaro
authors.initials: Y
authors.lastname: Matsumoto
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ito
authors.forename: Motonari
authors.initials: M
authors.lastname: Uesugi
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kittaka
mesh_terms: D004298:Dopamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*
chemical_list: D010756:Phosphoric Acids; D004298:Dopamine