59587-07-4Relevant articles and documents
Inhibition of siderophore biosynthesis by 2-triazole substituted analogues of 5′-O-[N-(salicyl)sulfamoyl]adenosine: Antibacterial nucleosides effective against Mycobacterium tuberculosis
Gupte, Amol,Boshoff, Helena I.,Wilson, Daniel J.,Neres, Jo?o,Labello, Nicholas P.,Somu, Ravindranadh V.,Xing, Chengguo,Barry III, Clifton E.,Aldrich, Courtney C.
experimental part, p. 7495 - 7507 (2009/12/07)
The synthesis, biochemical, and biological evaluation of a systematic series of 2-triazole derivatives of 5′-O-[N-(salicyl)sulfamoyl]adenosine (Sal-AMS) are described as inhibitors of aryl acid adenylating enzymes (AAAE) involved in siderophore biosynthesis by Mycobacterium tuberculosis. Structure-activity relationships revealed a remarkable ability to tolerate a wide range of substituents at the 4-position of the triazole moiety, and a majority of the compounds possessed subnanomolar apparent inhibition constants. However, the in vitro potency did not always translate into whole cell biological activity against M. tuberculosis, suggesting that intrinsic resistance plays an important role in the observed activities. Additionally, the well-known valence tautomerism between 2-azidopurines and their fused tetrazole counterparts led to an unexpected facile acylation of the purine N-6 amino group.
Synthesis and biological evaluation of β-D-pentofuranonucleoside derivatives of 2-azidoadenine and 6-azidopurines
Mathe, Christophe,Lioux, Thierry,Gosselin, Gilles
, p. 605 - 609 (2007/10/03)
β-D-pentofuranonucleoside derivatives of 2-azidoadenine and 6-azidopurines have been synthesized. The azido-tetrazolo tautomerism observed on such nucleoside analogues has been studied. The compounds were tested for their activity against HIV and HBV but they did not show significant antiviral effect.