32464-93-0Relevant articles and documents
Triazoxins: Novel nucleosides with anti-Giardia activity
Chi, Miguel,Das, Siddhartha,De Chatterjee, Atasi,Patterson, Steven E.,Pogula, Praveen K.,VanKoten, Harrison W.
, (2020)
Novel nucleoside analogues named “triazoxins” were synthesized. Of these, two analogues were found to be highly effective against Giardia lamblia, an intestinal parasite and a major cause of waterborne infection, worldwide. While compound 7 reduced the growth of trophozoites in culture (IC50, ~5 μM), compound 21 blocked the in vitro cyst production (IC50 ~5 μM). Compound 21 was also effective against trophozoites (IC50, ~36 μM). A third analogue (compound 8) was effective against both trophozoites (IC50, ~36 μM) and cysts (IC50, ~20 μM) although at higher concentration. Thus triazoxin analogues are unique and exhibit morphology (i.e., trohozoites or cysts) -specific effects against Giardia.
Structure-function studies on nucleoside antibiotic mureidomycin A: Synthesis of 5′-functionalised uridine models
Gentle, Caragh A.,Harrison, Stephen A.,Inukai, Masatoshi,Bugg, Timothy D. H.
, p. 1287 - 1294 (2007/10/03)
The importance of functional groups in nucleoside antibiotic mureidomycin A (MRD A) for biological activity has been examined by derivatisation of samples of the natural product, and by synthesis of uridine-containing analogues. N-Succinyl and di- and tri-acetyl derivatives MRD A have been prepared, and were found to have reduced activity as inhibitors of E. coli translocase I. The enamide alkene of MRD A was found to be extremely resistant towards hydrogenation by a variety of reagents. Several 5′-functionalised uridine derivatives were synthesised from N3-p-methoxybenzyl-2′,3′-isopropylideneuridine. A series of 5′-aminoacyl derivatives were prepared, and the 3-aminopropionyl (IC50 260 μM) and 7-aminoheptanoyl (IC50 1.5 mM) derivatives were found to act as reversible inhibitors. An analogue mimicking the carboxy terminus of MRD A was synthesised, and also acted as an inhibitor of translocase I (IC50 1.9 mM). A phosphonate analogue designed as a possible suicide inhibitor showed modest inhibition (IC50 3.7 mM), which was shown to be irreversible.
Fully synthetic stereoselective routes to the differentially protected subunits of the tunicamycins
Danishefsky,DeNinno,Chen,Boisvert,Barbachyn
, p. 5810 - 5818 (2007/10/02)
Total synthesis of the two subunits corresponding to tunicamycins have been achieved. One of the key steps involves a cyclocondensation reaction of 7-carbon aldehydo nucleoside with activated diene 8 under catalysis with stannic chloride (see 7 + 8→9a,b). Stereospecific Fitzsimmons cycloadditions of dibenzyl azodicarboxylate to galactal 12 and glucal 22 simplified construction of the amino pyranose systems.
