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-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.
Guetzoyan
Lucie J
LJ
Department of Chemistry, University of Warwick, CV4 7AL, UK.
Spooner
Robert A
RA
Lord
J Michael
JM
Roberts
Lynne M
LM
Clarkson
Guy J
GJ
D001547:Benzaldehydes / Q000737:chemistry / Q000494:pharmacology; D001692:Biological Transport / Q000187:drug effects; D003500:Cyclization; D006367:HeLa Cells; D006801:Humans; D006835:Hydrazones / Q000737:chemistry* / Q000494:pharmacology*; D010084:Oxidation-Reduction; D011743:Pyrimidines / Q000737:chemistry / Q000494:pharmacology; D022621:Shiga Toxin / Q000378:metabolism*; D014230:Triazoles / Q000737:chemistry* / Q000494:pharmacology*
C495416:4-hydroxy-3-methoxy-(5,6,7,8-tetrahydro(1)benzothieno(2,3-d)pyrimidin-4-yl)hydrazone benzaldehyde; D001547:Benzaldehydes; D006835:Hydrazones; D011743:Pyrimidines; D014230:Triazoles; D022621:Shiga Toxin