Chromophore-modified antitumor anthracenes. 1. Cytotoxic activity of 9-acyloxy 1,5-dichloroanthracene analogues

As part of our program aimed at exploring the effect of introducing side chains to the anthracenone chromophore, we synthesized a novel series of 9-acyloxy 1,5-dichloroanthracene derivatives. Reduction of 1,5-dichloro anthraquinone with stannous chloride in boiling HCl and acetic acid with concomitant selective acylation led to the corresponding 9-acyloxy 1,5-dichloroanthracenes. These compounds were evaluated in vitro for their ability to inhibit the growth of human oral epidermoid carcinoma (KB) cells, human cervical carcinoma (GBM8401) cells and Chinese hamster ovary (CHO) cells, respectively. Compounds 3g, 3j and 3k were more potent against GBM cells than doxorubicin. Compounds 3j and 3v were more potent against KB cells than doxorubicin. Although compound 3j was active against both GBM and KB cells which was not cytotoxic to CHO cells. The implications of 9-acyloxy-1,5-dichloroanthracene analogs as potential anticancer agents are discussed.