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Issue 20, 2019
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Synthesis of amino acid derivatives of 5-alkoxy-3,4-dihalo-2(5H)-furanones and their preliminary bioactivity investigation as linkers

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Abstract

A series of amino acid derivatives are successfully synthesized via a metal-free C–N coupling reaction of 5-alkoxy-3,4-dihalo-2(5H)-furanones and amino acids. Their structures are well characterized with 1H NMR, 13C NMR, ESI-MS and elemental analysis. As potential linkers of the 2(5H)-furanone unit with other drug moieties containing a hydroxyl or amino group, the effect of amino acids is investigated by comparison with other 2(5H)-furanone compounds by constructing C–O/C–S bonds. The preliminary results of the biological activity assay by the MTT method on a series of cancer cell lines in vitro reveal that the introduction of amino acids basically has no toxic effect. This can lead to these 2(5H)-furanone derivatives being further well-linked with other bioactive moieties with amino or hydroxy groups as expected. Thus, the biological activity assay gives a direction for the design of bioactive 2(5H)-furanones based on these amino acid linkers.

Graphical abstract: Synthesis of amino acid derivatives of 5-alkoxy-3,4-dihalo-2(5H)-furanones and their preliminary bioactivity investigation as linkers

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Supplementary files

Article information


Submitted
31 Mar 2019
Accepted
02 May 2019
First published
02 May 2019

Org. Biomol. Chem., 2019,17, 5138-5147
Article type
Paper

Synthesis of amino acid derivatives of 5-alkoxy-3,4-dihalo-2(5H)-furanones and their preliminary bioactivity investigation as linkers

S. Luo, K. Yang, J. Lin, J. Gao, X. Wu and Z. Wang, Org. Biomol. Chem., 2019, 17, 5138 DOI: 10.1039/C9OB00736A

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