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A series of hydroxyanthraquinones having an alkylating N-mustard pharmacophore at 1'-position were synthesized via a bioisostere approach to evaluate their cytotoxicity against four tumor cell lines (MDA-MB-231, HeLa, MCF-7 and A549). These compounds displayed significant in vitro cytotoxicity against MDA-MB-231 and MCF-7 cells, reflecting the excellent selectivity for the human breast cancer. Among them, compound 5k was the most cytotoxic with IC50 value of 0.263 nM and is more potent than DXR (IC50 = 0.294 nM) in inhibiting the growth of MCF-7 cells. The excellent cytotoxicity and good selectivity of compound 5k suggest that it could be a promising lead for further design and development of anticancer agents, especially for breast cancer., (Copyright © 2015 Elsevier Masson SAS. All rights reserved.)

In an attempt to develop potent and selective antitumor agents, a series of 6- and 2-(1-substituted-thio-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-diones were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against BEL-7402, HT-29 and SPC-A1 cell lines. The pharmacological results showed that most of the prepared compounds displayed the excellent selective cytotoxicity toward HT-29 cells. From the structure-activity relationships we may conclude that the introduction of a thioether functional group at the 1'-position in the side chain of shikonin is associated with an increase in cytotoxicity.

1,4-Dihydroxyanthraquinones are widely featured in numerous natural products and drugs. It is important to be able to functionalize the 1,4-dihydroxyanthraquinone skeleton through a simple yet efficient transformation, which could be potentially useful for the drug discovery process. We describe herein a simple and efficient method to derivatize 1,4-dihydroxyanthraquinone by using a modified Marschalk reaction. This method provides a clear advantage over traditional approaches, which often require the protection and deprotection of the OH groups. We also demonstrate the applicability of this reaction to other hydroxyanthraquinones and aminoanthraquinones. [ABSTRACT FROM AUTHOR]

Abstract: A simple and efficient method for derivatization of hydroxyanthraquinone natural product emodin through catalyst-free Mannich reaction is described. The method allows the modification of emodin skeleton at 2-position. This new derivatization strategy to emodin provides a clear advantage over traditional approaches, due to its easy operation and efficiency that does not involve the protection and deprotection. [Copyright &y& Elsevier]

A simple, mild, and efficient method for the preparation of the target compounds is presented. [ABSTRACT FROM AUTHOR]

The protocol allows the access to various Mannich bases which are required for structure-activity relationship studies. [ABSTRACT FROM AUTHOR]