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Issue 8, 2017
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Synthesis and antiproliferative activity of sulfa-Michael adducts and thiochromenes derived from carbohydrates

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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.

Graphical abstract: Synthesis and antiproliferative activity of sulfa-Michael adducts and thiochromenes derived from carbohydrates

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Publication details

The article was received on 15 Dec 2016, accepted on 09 Mar 2017 and first published on 10 Mar 2017


Article type: Paper
DOI: 10.1039/C6NJ03940E
Citation: New J. Chem., 2017,41, 3154-3162
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    Synthesis and antiproliferative activity of sulfa-Michael adducts and thiochromenes derived from carbohydrates

    V. Luque-Agudo, J. Albarrán-Velo, J. G. Fernández-Bolaños, O. López, M. E. Light, J. M. Padrón, I. Lagunes, E. Román, J. A. Serrano and M. V. Gil, New J. Chem., 2017, 41, 3154
    DOI: 10.1039/C6NJ03940E

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