91777-77-4Relevant academic research and scientific papers
Mesoionic pyridazine ribonucleosides. A novel biologically active nucleoside metabolite
Bambury,Feeley,Lawton,Weaver,Wemple
, p. 1613 - 1621 (2007/10/02)
4-Cyano-3-oxido-1-β-D-ribofuranosylpyridazinium (10a) has been prepared from 4-cyano-3(2H)-pyridazinone by using a low-temperature, kinetically controlled, silyl Hilbert-Johnson reaction followed by deblocking of the resulting triacetate derivative with NaHCO3 in methanol. 10a is apparently the first example of a mesoionic analogue of a pyrimidine nucleoside. It was discovered as a urine metabolite of 4-cyano-3(2H)-pyridazinone in mice. 10a possesses Gram-negative antibacterial activity in vivo against a systemic Escherichia coli infection in mice with an ED50 of 25-50 mg/kg. A series of 4-substituted 3-oxidooxyridazinium ribonucleosides, 11a-h, were synthesized as analogues of 10a. 4-Chloro-3-oxido-1-β-D-ribofuranosylpyridazinium (11a) was found to be several times more active than 10a against E. coli in vitro although it showed no in vivo activity.
Mesoionic Pyridazine and Pyridine Nucleosides. An Unusual Biologically Active Nucleoside Metabolite
Bambury, Ronald E.,Feeley, Daniel T.,Lawton, Gerald C.,Weaver, John M.,Wemple, James
, p. 422 - 423 (2007/10/02)
An in vivo process in mice leading to the mesoionic 3-oxidopyridazinium riboside, (3b), can also be accomplished via a kinetically controlled silyl Hilbert-Johnson reaction.
