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The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans.
Rixson, James E; Abraham, James R; Egoshi, Yuki; Skelton, Brian W; Young, Kelly; Gilbert, Jayne; Sakoff, Jennette A; Gericke, Kersten M; McCluskey, Adam; Stewart, Scott G.
Afiliación
  • Rixson JE; The School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA 6009, Australia.
  • Abraham JR; The School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA 6009, Australia.
  • Egoshi Y; The School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA 6009, Australia; Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
  • Skelton BW; Centre for Microscopy, Characterisation and Analysis, The University of Western Australia, Crawley, WA 6009, Australia.
  • Young K; Department of Medical Oncology, Calvary Mater Newcastle Hospital, Edith Street, Waratah, 2298 NSW, Australia.
  • Gilbert J; Department of Medical Oncology, Calvary Mater Newcastle Hospital, Edith Street, Waratah, 2298 NSW, Australia.
  • Sakoff JA; Department of Medical Oncology, Calvary Mater Newcastle Hospital, Edith Street, Waratah, 2298 NSW, Australia.
  • Gericke KM; Bayer Pharma AG, Medicinal Chemistry, 42096 Wuppertal, Germany.
  • McCluskey A; Chemistry Building, The University of Newcastle, University Drive, Callaghan, NSW 2308, Australia. Electronic address: Adam.McCluskey@newcastle.edu.au.
  • Stewart SG; The School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA 6009, Australia. Electronic address: scott.stewart@uwa.edu.au.
Bioorg Med Chem ; 23(13): 3552-65, 2015 Jul 01.
Article en En | MEDLINE | ID: mdl-25979375
An efficient and divergent methodology for the synthesis of new anthracenone-pyranones and anthracenone-furans is described. Key reactions discussed in these syntheses include an aldehyde promoted annulation with a ß-keto-sulfoxide, a domino alkyne insertion/carbonylation/Nu-acylation and a DMEDA promoted Castro-Stephens reaction. We also report the in vitro growth inhibition of these compounds in a range of human cancer cells. The natural product BE-26554A displayed good cell growth activity on BE2-C neuroblastoma and SMA glioblastoma cell lines at 0.17 and 0.16µM (GI50), respectively. Of note, were a CF3 functionalised anthracenone 4-pyranone (chromone) derivative 22, and an anthracenone-furan derivative 54 which displayed 0.20µM and 0.38µM growth inhibition, respectively, in the BE2-C neuroblastoma cell line.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Cromonas / Furanos / Antracenos / Antineoplásicos Límite: Humans Idioma: En Revista: Bioorg Med Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2015 Tipo del documento: Article País de afiliación: Australia Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Cromonas / Furanos / Antracenos / Antineoplásicos Límite: Humans Idioma: En Revista: Bioorg Med Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2015 Tipo del documento: Article País de afiliación: Australia Pais de publicación: Reino Unido