title: 7-Azamelatonin: efficient synthetic routes, excited-state double proton transfer properties and biomedical implications.
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.
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei, 106, Taiwan, ROC.
authors.forename: Pei-Wen
authors.initials: PW
authors.lastname: Wu
authors.forename: Yi-Ming
authors.initials: YM
authors.lastname: Cheng
authors.forename: Wan-Ting
authors.initials: WT
authors.lastname: Hsieh
authors.forename: Yu-Hsiu
authors.initials: YH
authors.lastname: Wang
authors.forename: Ching-Yen
authors.initials: CY
authors.lastname: Wei
authors.forename: Pi-Tai
authors.initials: PT
authors.lastname: Chou
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008550:Melatonin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011522:Protons; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: C530677:7-azamelatonin; D011522:Protons; D008550:Melatonin