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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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Supplementary files

Article information


Submitted
01 Sep 2015
Accepted
23 Sep 2015
First published
23 Sep 2015

Org. Biomol. Chem., 2015,13, 11292-11301
Article type
Paper
Author version available

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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