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7‐Azamelatonin: Efficient Synthetic Routes, Excited‐State Double Proton Transfer Properties and Biomedical Implications
Author(s) -
Wu PeiWen,
Cheng YiMing,
Hsieh WanTing,
Wang YuHsiu,
Wei ChingYen,
Chou PiTai
Publication year - 2007
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200700043
Subject(s) - excited state , proton , yield (engineering) , aqueous solution , chemical physics , property (philosophy) , chemistry , materials science , computational chemistry , combinatorial chemistry , nanotechnology , atomic physics , physics , nuclear physics , philosophy , epistemology , metallurgy
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.