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Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking
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Guetzoyan, Lucie J., Spooner, Robert A. , Lord, Mike, Roberts, L. M. (Lynne M.) and Clarkson, Guy J. (2010) Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking. European Journal of Medicinal Chemistry, Vol.45 (No.1). pp. 275-283. doi:10.1016/j.ejmech.2009.10.007 ISSN 0223-5234.
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Official URL: http://dx.doi.org/10.1016/j.ejmech.2009.10.007
Abstract
The oxidative cyclisation of a range of benzothieno[2,3-d]pyrimidine hydrazones (7a–j) to the 1,2,4-triazolo[4,3-c]pyrimidines (8a–j) catalysed by lithium iodide or to the 1,2,4-triazolo[1,5-c]pyrimidines (10a–j) with sodium carbonate is presented. A complementary synthesis of the 1,2,4-triazolo[1,5-c]pyrimidines starting from the amino imine 11 is also reported. The effect of these compounds on Shiga toxin (STx) trafficking in HeLa cells and comparison to the previously reported Exo2 is also detailed.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry Q Science > QR Microbiology |
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Science > Life Sciences (2010- ) > Biological Sciences ( -2010) |
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Library of Congress Subject Headings (LCSH): | Pyrimidines -- Research, Lithium compounds -- Research, Dimethyl sulfoxide, Gram-negative bacterial infections | ||||
Journal or Publication Title: | European Journal of Medicinal Chemistry | ||||
Publisher: | Elsevier Masson | ||||
ISSN: | 0223-5234 | ||||
Official Date: | January 2010 | ||||
Dates: |
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Volume: | Vol.45 | ||||
Number: | No.1 | ||||
Page Range: | pp. 275-283 | ||||
DOI: | 10.1016/j.ejmech.2009.10.007 | ||||
Status: | Peer Reviewed | ||||
Access rights to Published version: | Restricted or Subscription Access | ||||
Funder: | Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC) | ||||
Grant number: | BB/E012450/1 (BBSRC) |
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