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Issue 46, 2015
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Application of Mannich bases to the synthesis of hydroxymethylated isoflavonoids as potential antineoplastic agents

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Abstract

The regiospecific Mannich aminomethylation of 7-hydroxyisoflavonoids using bis(N,N-dimethylamino)methane afforded C-8 substituted N,N-dimethylaminomethyl adducts, and the regioselective aminomethylation of 5-hydroxy-7-methoxyisoflavonoids afforded predominantly the C-6 substituted N,N-dimethylaminomethyl adducts. Acetylation of these C-6 or C-8 Mannich bases with potassium acetate in acetic anhydride provided access to the corresponding acetoxymethyl derivatives that were subsequently converted to hydroxymethyl- and methoxymethyl-substituted 5-hydroxy- or 7-hydroxyisoflavonoids related to naturally occurring flavonoids. The C-8 acetoxymethyl, hydroxymethyl or methoxymethyl-substituted isoflavonoids possessed promising inhibitory potency in the low micromolar range in a prostate cancer PC-3 cell proliferation assay.

Graphical abstract: Application of Mannich bases to the synthesis of hydroxymethylated isoflavonoids as potential antineoplastic agents

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Publication details

The article was received on 01 Sep 2015, accepted on 23 Sep 2015 and first published on 23 Sep 2015


Article type: Paper
DOI: 10.1039/C5OB01828E
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 11292-11301
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    Application of Mannich bases to the synthesis of hydroxymethylated isoflavonoids as potential antineoplastic agents

    M. S. Frasinyuk, G. P. Mrug, S. P. Bondarenko, V. M. Sviripa, W. Zhang, X. Cai, M. V. Fiandalo, J. L. Mohler, C. Liu and D. S. Watt, Org. Biomol. Chem., 2015, 13, 11292
    DOI: 10.1039/C5OB01828E

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