Synthesis and antiproliferative activity of sulfa-Michael adducts and thiochromenes derived from carbohydrates
Synthesis and antiproliferative activity of sulfa-Michael adducts and thiochromenes derived from carbohydrates
The Michael addition reactions of carbohydrate-derived nitroalkenes with ethyl thioglycolate and 2-mercaptobenzyl alcohol were studied. Reactions were conducted under mild, solvent-free conditions with DABCO as a catalyst, affording the corresponding adducts in good yields. Furthermore, compounds resulting from the addition with 2-mercaptobenzyl alcohol were used as starting materials for the synthesis of chiral 3-nitro-2H-thiochromenes. For some of the compounds synthesized herein, the antioxidant and antiproliferative activities against a panel of human solid tumor cell lines were assayed and compared with those of carbohydrate-nitroalkene substrates.
Luque-Agudo, V.
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Albarran-Velo, J.
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Fernandez-Bolanos, J.G.
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Lopez, O.
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Light, Mark
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Padron, J.M.
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Lagunes, J.
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Roman, E.
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Serrano, J.A.
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Gil, M.V.
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Luque-Agudo, V.
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Albarran-Velo, J.
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Fernandez-Bolanos, J.G.
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Lopez, O.
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Light, Mark
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Padron, J.M.
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Lagunes, J.
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Roman, E.
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Serrano, J.A.
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Gil, M.V.
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Luque-Agudo, V., Albarran-Velo, J., Fernandez-Bolanos, J.G., Lopez, O., Light, Mark, Padron, J.M., Lagunes, J., Roman, E., Serrano, J.A. and Gil, M.V.
(2017)
Synthesis and antiproliferative activity of sulfa-Michael adducts and thiochromenes derived from carbohydrates.
New Journal of Chemistry.
(doi:10.1039/C6NJ03940E).
Abstract
The Michael addition reactions of carbohydrate-derived nitroalkenes with ethyl thioglycolate and 2-mercaptobenzyl alcohol were studied. Reactions were conducted under mild, solvent-free conditions with DABCO as a catalyst, affording the corresponding adducts in good yields. Furthermore, compounds resulting from the addition with 2-mercaptobenzyl alcohol were used as starting materials for the synthesis of chiral 3-nitro-2H-thiochromenes. For some of the compounds synthesized herein, the antioxidant and antiproliferative activities against a panel of human solid tumor cell lines were assayed and compared with those of carbohydrate-nitroalkene substrates.
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Accepted/In Press date: 9 March 2017
e-pub ahead of print date: 10 March 2017
Organisations:
Characterisation and Analytics
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Local EPrints ID: 407583
URI: http://eprints.soton.ac.uk/id/eprint/407583
ISSN: 1144-0546
PURE UUID: b95781f8-2cb2-4c1d-9f09-6b0571389109
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Date deposited: 16 Apr 2017 16:58
Last modified: 16 Mar 2024 05:14
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Contributors
Author:
V. Luque-Agudo
Author:
J. Albarran-Velo
Author:
J.G. Fernandez-Bolanos
Author:
O. Lopez
Author:
J.M. Padron
Author:
J. Lagunes
Author:
E. Roman
Author:
J.A. Serrano
Author:
M.V. Gil
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