Journal
TETRAHEDRON
Volume 67, Issue 48, Pages 9368-9375Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.09.133
Keywords
Fused heterocycles; Synthesis; Organic dyes; X-ray crystallography; Biological activity
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Funding
- Australian Research Council [DP0773011, DP0770653]
- Future Fellowship [FT0991910]
- National Breast Cancer Foundation of Australia
- Australian Synchrotron
- Australian Research Council [DP0773011, DP0770653] Funding Source: Australian Research Council
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The synthesis of six new compounds incorporating either a pyrazino[2,3-b]indolizine or indolizino[2,3-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. (C) 2011 Elsevier Ltd. All rights reserved.
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