- Inhibition of siderophore biosynthesis by 2-triazole substituted analogues of 5′-O-[N-(salicyl)sulfamoyl]adenosine: Antibacterial nucleosides effective against Mycobacterium tuberculosis
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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.
- 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.
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experimental part
p. 7495 - 7507
(2009/12/07)
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- Azido/Tetrazole Tautomerism in 2-Azidoadenine β -D-Pentofuranonucleoside Derivatives
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The β-D-ribofuranoside derivative of 2-azidoadenine and its 2′-deoxy-, 2′,3′-dideoxy- and 2′,3′ -dideoxy-2′,3′-didehydro counterparts have been synthesized. All these compounds were obtained through the preparation of their 2-chloro precursors. These were converted into their 2-hydrazino derivatives, which upon treatment with sodium nitrate in acid medium gave the target nucleosides. The azido/tetrazole tautomerism observed in such nucleoside analogues was studied in detail. The compounds were also tested for their activity against HIV and HBV, but did not show significant antiviral effects. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Lioux, Thierry,Gosselin, Gilles,Mathe, Christophe
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p. 3997 - 4002
(2007/10/03)
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- Synthesis and biological evaluation of β-D-pentofuranonucleoside derivatives of 2-azidoadenine and 6-azidopurines
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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.
- Mathe, Christophe,Lioux, Thierry,Gosselin, Gilles
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p. 605 - 609
(2007/10/03)
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- A facile synthesis of 2-azidoadenosine derivatives from guanosine as photoaffinity probes
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2-Azidoadenosine (1) was synthesized in an overall yield of 49% from guanosine via the reaction of 9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloropurine (2) with isoamyl nitrite and trimethylsilyl azide under neutral and anhydrous conditions. As photoaffinity probes, ATP analogues and the cap structure of eukaryotic mRNA bearing 2-azidoadenosine were synthesized.
- Higashiya, Seiichiro,Kaibara, Chitose,Fukuoka, Koichiro,Suda, Fuminori,Ishikawa, Masahide,Yoshida, Masasuke,Hata, Tsujiaki
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