7-Azamelatonin: efficient synthetic routes, excited-state double proton transfer properties and biomedical implications.
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.
Wu
Pei-Wen
PW
Department of Chemistry, National Taiwan University, Taipei, 106, Taiwan, ROC.
Cheng
Yi-Ming
YM
Hsieh
Wan-Ting
WT
Wang
Yu-Hsiu
YH
Wei
Ching-Yen
CY
Chou
Pi-Tai
PT
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
C530677:7-azamelatonin; D011522:Protons; D008550:Melatonin