Synthesis and cytotoxic activity of benzophenanthrolinone analogues of acronycine |
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Authors: | Bongui J B Elomri A Seguin E Tillequin F Pfeiffer B Renard P Pierré A Atassi G |
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Institution: | Laboratoire de Pharmacognosie de l'Université de Rouen-Haute Normandie, Faculté de Pharmacie, France. |
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Abstract: | Condensation of either 2-bromobenzoic acid (4) or 2-chloro-3-nitrobenzoic acid (5) with suitable aminoquinolines 6-8 afforded phenylquinolylamines 9-13. Acid mediated cyclization gave the corresponding 12H-benzob]1,7]phenanthrolin-7-ones 14 and 15, and 12H-benzob]1,10]phenanthrolin-7-ones 16-18. Compounds 14, 16, and 17 were subsequently N-methylated to 6-demethoxyacronycine and acronycine analogues 19-21, whereas reduction of the aromatic nitro group of 18 gave the amino derivative 22. Unsubstituted 12H-benzob]1,10]phenanthrolin-7-ones 16, 17, 20, and 21 were devoid of significant cytotoxic activity, whereas 18 and 22, bearing a nitrogen substituent at position 11, were significantly active. Unsubstituted 12H-benzob]1,7]phenanthrolin-7-ones 14 and 19, which include a pyridine nitrogen in the same 4-position as the pyran oxygen of acronycine exhibited cytotoxic activities within the same range of magnitude as acronycine itself. |
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