Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/66424
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dc.contributor.author | Bloch, W. | - |
dc.contributor.author | Derwent - Smith, S. | - |
dc.contributor.author | Issa, F. | - |
dc.contributor.author | Morris, J. | - |
dc.contributor.author | Rendina, L. | - |
dc.contributor.author | Sumby, C. | - |
dc.date.issued | 2011 | - |
dc.identifier.citation | Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2011; 67(48):9368-9375 | - |
dc.identifier.issn | 0040-4020 | - |
dc.identifier.issn | 1464-5416 | - |
dc.identifier.uri | http://hdl.handle.net/2440/66424 | - |
dc.description.abstract | 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. © 2011 Elsevier Ltd. All rights reserved. | - |
dc.description.statementofresponsibility | Witold M. Bloch, Stephanie M. Derwent-Smith, Fatiah Issa, Jonathan C. Morris, Louis M. Rendina and Christopher J. Sumby | - |
dc.description.uri | http://www.journals.elsevier.com/tetrahedron/ | - |
dc.language.iso | en | - |
dc.publisher | Pergamon-Elsevier Science Ltd | - |
dc.rights | Copyright Elsevier 2011 | - |
dc.source.uri | http://dx.doi.org/10.1016/j.tet.2011.09.133 | - |
dc.subject | Fused Heterocycles | - |
dc.subject | Synthesis | - |
dc.subject | Organic dyes | - |
dc.subject | X-ray crystallography | - |
dc.subject | Biological Activity | - |
dc.title | Fused pyrazino [2,3-b]indolizine and indolizino[2,3-b]quioxaline derivatives; synthesis, structures and properties | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1016/j.tet.2011.09.133 | - |
dc.relation.grant | http://purl.org/au-research/grants/arc/DP0773011 | - |
dc.relation.grant | http://purl.org/au-research/grants/arc/DP0770653 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Bloch, W. [0000-0003-1084-1287] | - |
dc.identifier.orcid | Sumby, C. [0000-0002-9713-9599] | - |
Appears in Collections: | Aurora harvest Environment Institute publications IPAS publications |
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hdl_66424.pdf | Accepted version | 598.3 kB | Adobe PDF | View/Open |
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