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Issue 3, 2019
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Fluorine substituted methoxyphenylalkyl amides as potent melatonin receptor agonists

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Abstract

A series of fluorine substituted methoxyphenylalkyl amides were prepared with different orientations of the fluorine and methoxy groups with respect to the alkylamide side chain and with alkyl sides of differing lengths (n = 1–3). β-Dimethyl and α-methyl derivatives were also synthesised. The compounds were tested as melatonin agonists and antagonists using the pigment aggregation of Xenopus melanophores as the biological assay. A number of these compounds were potent melatonin agonists, the potency depending on the length of the alkyl chain, the orientation of the methoxy and fluorine substituents, the amide chain length and, for the ethyl side-chain analogues, the presence of β-substituents.

Graphical abstract: Fluorine substituted methoxyphenylalkyl amides as potent melatonin receptor agonists

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Publication details

The article was received on 07 Dec 2018, accepted on 10 Feb 2019 and first published on 11 Feb 2019


Article type: Research Article
DOI: 10.1039/C8MD00604K
Med. Chem. Commun., 2019,10, 460-464

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    Fluorine substituted methoxyphenylalkyl amides as potent melatonin receptor agonists

    A. Tsotinis, R. Kompogennitaki, I. Papanastasiou, P. J. Garratt, A. Bocianowska and D. Sugden, Med. Chem. Commun., 2019, 10, 460
    DOI: 10.1039/C8MD00604K

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