Synthesis and Cytotoxic Activity of Benzophenanthrolinone Analogues of Acronycine
| Autor: | Bruno Pfeiffer, Pierre Renard, Jean-Bernard Bongui, Francois Tillequin, Ghanem Atassi, Abdelhakim Elomri, Elisabeth Seguin, Alain Pierre |
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| Rok vydání: | 2001 |
| Předmět: |
chemistry.chemical_classification
Ketone Acronine Stereochemistry Substituent Aromatic amine General Chemistry General Medicine Antineoplastic Agents Phytogenic Chemical synthesis Mass Spectrometry Mice chemistry.chemical_compound chemistry Pyran Drug Discovery Pyridine Nitro Animals Indicators and Reagents Aminoquinolines Leukemia L1210 Phenanthrolines |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 49:1077-1080 |
| ISSN: | 1347-5223 0009-2363 |
| Popis: | 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-benzo[b][1,7]phenanthrolin-7-ones 14 and 15, and 12H-benzo[b][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-benzo[b][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-benzo[b][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. |
| Databáze: | OpenAIRE |
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