Synthesis and Cytotoxic Activity of Acronycine Analogues in the Benzo[c]pyrano[3,2-h]acridin-7-one and Naphtho[1,2-b][1,7] and [1,10]-Phenanthrolin-7(14H)-one Series

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概要

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• Condensation of 1-bromo-2-naphthalenecarboxylic acid (9) with 7-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamine (13) followed by acid-mediated cyclization afforded 6-methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[c]pyrano[3, 2-h]acridin-7-one (15), which was further methylated into 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2-h]acridin-7-one (benzo[c]acronycine) (3) and 6,7-dimethoxy-3,3-dimethyl-3H-benzo[c]pyrano[3,2-h]acridine (4). Osmium tetroxide oxidation of 15 gave the (±)-cis-diol 16, which afforded the benzopyranoacridine and benzopyranoacridone esters 17-22 upon acylation. Condensation of 9 with suitable aminoquinolines 23-25 afforded the carboxylic naphthylquinolylamines 26-28. Cyclization gave the corresponding naphtho[1,2-b][1,10]-phenanthrolin-7(14H)-ones 29 and 30, and naphtho[1,2-b][1,7]-phenanthrolin-7(14H)-one 31, which were subsequently N-methylated to the desired 14-methylnaphtho[1,2-b][1,10] and [1,7]-phenanthrolinones 6, 7, and 8. Benzo[c]pyrano[3, 2-h]acridin-7-one derivatives 3, 16, and 22 displayed cytotoxic activities within the same range of magnitude as acronycine itself, whereas 7-alkoxybenzo[c]pyrano[3,2-h]acridine and 7-acyloxybenzo[c]pyrano[3,2-h]acridine derivatives 4 and 17-21 were less active when tested against L1210 murine leukemia cells in vitro. Naphthophenanthrolinones 6-8 were devoid of significant antiproliferative activity, but compounds 29-31 bearing no substituent on the nitrogen atom at position 14 were more potent.

• 公益社団法人日本薬学会の論文
• 2005-12-01

著者

• Pfeiffer Bruno

  Institut De Recherches Servier Division Recherche Cancerologie

• PIERRE Alain

  Institut de Recherches Servier, Division Recherche Cancerologie

• Pierre Alain

  Institut De Recherches Servier Division Recherche Cancerologie

• Bongui Jean-bernard

  Laboratoire De Pharmacognosie De L'universite De Rouen-haute Normandie Umr 6014 Cnrs Faculte De

• Elomri Abdelhakim

  Laboratoire De Pharmacognosie De L'universite De Rouen-haute Normandie Umr 6014 Cnrs Faculte De

• Seguin Elisabeth

  Lab. De Pharmacognosie Ufr De Medecine Pharmacie Rouen

• Seguin Elisabeth

  Laboratoire De Pharmacognosie Ufr De Medecine Pharmacie Rouen

• Tillequin Francois

  Laboratoire De Pharmacognosie De L'universite Paris Descartes

• Tillequin F

  Laboratoire De Pharmacognoise De 1'universite Rene Descartes Umr/cnrsn ^○8638 Faculte Des Scien

• BONGUI Jean

  Laboratoire de Pharmacognosie de l'Universite de Rouen-Haute Normandie, UMR 6014 CNRS, Faculte de Ph

• CAHARD Dominique

  UMR 6014 CNRS de l'IRCOF, Universite de Rouen

• Cahard Dominique

  Umr 6014 Cnrs De L'ircof Universite De Rouen

• Seguin Elisabeth

  Laboratoire de Pharmacognosie de l'Universite de Rouen-Haute Normandie, UMR 6014 CNRS, Faculte de Pharmacie

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