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Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking

By Lucie J. Guetzoyan, Robert A. Spooner, Mike Lord, L. M. (Lynne M.) Roberts and Guy J. Clarkson

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

Topics: QD, QR
Publisher: Elsevier Masson
Year: 2010
OAI identifier: oai:wrap.warwick.ac.uk:3289

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Citations

  1. (1981). 1277– 1280. [19] For the oxidation of sodium iodide by sulfoxides see a
  2. (2008). 3848–3853. See also the sulphur catalysed oxidation of aminomethylpyridines to imidazopyridines in
  3. (2007). 999–1004. [3] a
  4. (2007). For an example of cyclisation with activated acid derivatives see
  5. (1978). for examples of cyclisation with orthoformates see a doi
  6. (2004). For examples of the arial oxidation of other diamino heterocycles see a
  7. (1999). For reviews on the Dimroth rearrangement in triazolopyrimidine systems see a doi
  8. (1999). For reviews on the synthesis of pyrimidine triazoles see
  9. (2007). For similar cyclisations of amino imines with aldehydes but done in DMF/HOAc see a
  10. Program for the Refinement of Crystal Structures, doi

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