Fused pyrazino[2,3-b]indolizine and indolizino[2,3-b]quinoxaline derivatives; synthesis, structures, and properties |
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Authors: | Witold M BlochStephanie M Derwent-Smith Fatiah IssaJonathan C Morris Louis M RendinaChristopher J Sumby |
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Institution: | a School of Chemistry & Physics, The University of Adelaide, Adelaide, SA 5005, Australia b School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia c School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia |
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Abstract: | The synthesis of six new compounds incorporating either a pyrazino2,3-b]indolizine or indolizino2,3-b]quinoxaline core are reported in good yield (58-87%). The intermediates for the key cyclization reaction for one set of compounds (5a-c), with a sterically demanding 3,5-dimethylpyrazole group in the 5-position of the core, were found to be mono-substituted. These intermediates could be isolated and cyclized by heating under acid-catalyzed conditions. To further demonstrate the versatility of the chemistry, compounds 6a-c were synthesized in 58-68% yields. Compounds 5a-c are non-planar in solution and the solid-state, while 6a-c have close to planar conformations, pointing to weak hydrogen bonds between the acidic C-Hs and the adjacent azine nitrogen atoms. The cytotoxicity of the six newly synthesized and three previously prepared compounds was assessed against a human glioblastoma multiforme cell line. |
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Keywords: | Fused heterocycles Synthesis Organic dyes X-ray crystallography Biological activity |
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