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

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-tri...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2010, Vol.45 (1), p.275-283
Main Authors: Guetzoyan, Lucie J., Spooner, Robert A., Lord, J. Michael, Roberts, Lynne M., Clarkson, Guy J.
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Benzaldehydes - chemistry
Benzaldehydes - pharmacology
Biological and medical sciences
Biological Transport - drug effects
Cyclization
Dimroth rearrangement
DMSO
Exo2
General aspects
HeLa Cells
Humans
Hydrazones - chemistry
Hydrazones - pharmacology
Lithium iodide
Medical sciences
Oxidation-Reduction
Pharmacology. Drug treatments
Pyrimidines - chemistry
Pyrimidines - pharmacology
Pyrimidyl hydrazone
Shiga toxin
Shiga Toxin - metabolism
Sodium carbonate
Triazoles - chemistry
Triazoles - pharmacology
Triazolopyrimidine
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Summary: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 [Display omitted]
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2009.10.007