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The first total syntheses of natural phenanthrene alkaloids, namely, uvariopsamine (1), noruvariopsamine (2), 8-hydroxystephenanthrine (3), 8-methoxyuvariopsine (4), thalihazine (5), and secophoebine (6), have been realized. In addition, their in vitro antimalarial activity against the multidrug-resistant K1 strain of Plasmodium falciparum and in vitro cytotoxic activity against the human nasopharynx carcinoma (KB), small cell lung cancer (NCI-H187), and breast cancer (MCF7) human cancer cell lines were investigated. All the phenanthrene alkaloids showed significant antiplasmodial activity (IC 50 1.07-7.41 µM), and most compounds displayed low to no toxicity against the three cancer cell lines tested. Particularly, 3 exhibited the best antimalarial activity with an IC 50 value of 1.07 µM, no toxicity to NCI-H187 (IC 50  &gt; 50 µM), and low toxicity against KB (IC 50 24.53 µM) and MCF7 (IC 50 42.67 µM) cell lines.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

First Total Syntheses of Natural Phenanthrene Alkaloids, Uvariopsamine, Noruvariopsamine, 8-Hydroxystephenanthrine, 8-Methoxyuvariopsine, Thalihazine, and Secophoebine, and Their Potential as Antimalarial Agents