Issue 46, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
01 Sep 2015
Accepted
23 Sep 2015
First published
23 Sep 2015

Org. Biomol. Chem., 2015,13, 11292-11301

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements