Synthesis and Cytotoxic Activity of Benzophenanthrolinone Analogues of Acronycine.
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- BONGUI Jean-Bernard
- Laboratoire de Pharmacognosie de l’Université de Rouen-Haute Normandie
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- ELOMRI Abdelhakim
- Laboratoire de Pharmacognosie de l’Université de Rouen-Haute Normandie
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- SEGUIN Elisabeth
- Laboratoire de Pharmacognosie de l’Université de Rouen-Haute Normandie
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- TILLEQUIN Francois
- Laboratoire de Pharmacognosie de l’Université René Descartes, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques
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- PFEIFFER Bruno
- A.D.I.R. et Compagnie
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- RENARD Pierre
- A.D.I.R. et Compagnie
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- PIERRE Alain
- Institut de Recherche Servier
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- ATASSI Ghanem
- Institut de Recherche Servier
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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-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.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 49 (9), 1077-1080, 2001
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679141158912
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- NII Article ID
- 110003616052
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- NII Book ID
- AA00602100
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- COI
- 1:CAS:528:DC%2BD3MXmsFyksbw%3D
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 5892570
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- PubMed
- 11558589
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed