7-Azamelatonin: Efficient synthetic routes, excited-state double proton transfer properties and biomedical implications

Pei Wen Wu; Yi Ming Cheng; Wan Ting Hsieh; Yu Hsiu Wang; Ching Yen Wei; Pi Tai Chou

doi:10.1002/cmdc.200700043

7-Azamelatonin: Efficient synthetic routes, excited-state double proton transfer properties and biomedical implications

Pei Wen Wu
, Yi Ming Cheng
, Wan Ting Hsieh
, Yu Hsiu Wang
, Ching Yen Wei
, Pi Tai Chou

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

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 ∼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.

Original language	English (US)
Pages (from-to)	1071-1075
Number of pages	5
Journal	ChemMedChem
Volume	2
Issue number	7
DOIs	https://doi.org/10.1002/cmdc.200700043
State	Published - Jul 9 2007
Externally published	Yes

Keywords

7-azamelatonin
DFT
Docking
Excited-state double proton transfer (ESDPT)

ASJC Scopus subject areas

Drug Discovery
General Pharmacology, Toxicology and Pharmaceutics
Molecular Medicine
Biochemistry
Pharmacology
Organic Chemistry

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10.1002/cmdc.200700043

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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 ∼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.",

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language = "English (US)",

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T2 - Efficient synthetic routes, excited-state double proton transfer properties and biomedical implications

AU - Wu, Pei Wen

AU - Cheng, Yi Ming

AU - Hsieh, Wan Ting

AU - Wang, Yu Hsiu

AU - Wei, Ching Yen

AU - Chou, Pi Tai

PY - 2007/7/9

Y1 - 2007/7/9

N2 - 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.

AB - 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.

KW - 7-azamelatonin

KW - DFT

KW - Docking

KW - Excited-state double proton transfer (ESDPT)

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JO - ChemMedChem

JF - ChemMedChem

IS - 7

ER -

7-Azamelatonin: Efficient synthetic routes, excited-state double proton transfer properties and biomedical implications

Abstract

Keywords

ASJC Scopus subject areas

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