2012
DOI: 10.1016/j.bmcl.2012.08.093
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Synthesis and in vitro antitumour screening of 2-(β-d-xylofuranosyl)thiazole-4-carboxamide and two novel tiazofurin analogues with substituted tetrahydrofurodioxol moiety as a sugar mimic

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Cited by 25 publications
(5 citation statements)
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“…In fact, although it is the first time that the alkylation of the non-anomeric position of the acyl oxonium is reported for C 2 -methylated pentoses, this phenomenon has already been described during the reaction of silyl enol ethers with peracylated- D -ribofuranose catalyzed by stannic chloride to produce C -nucleosides ( Yokoyama et al, 1982 ; Berber et al, 2001 ). Since then, a few other studies have reported this generally unexpected reactivity in C 2 -acylated sugars for other C -nucleophiles, such as allenyltributylstannane ( Chan et al, 2005 ), indium acetylenides ( Lubin-Germain et al, 2008 ), trimethylaluminum ( More and Campbell, 2009 ), cyanotrimethylsilane ( Popsavin et al, 2012 ), or zinc acetylenides ( Lemaire et al, 2014 ), suggesting that the small size of the nucleophile is the most decisive factor for the observed regioselectivity. The formation of the corresponding orthoesters is well known in the field of O -glycosylation, the latter serving as intermediates in the synthesis of oligosaccharides ( Kong, 2007 ).…”
Section: Resultsmentioning
confidence: 98%
“…In fact, although it is the first time that the alkylation of the non-anomeric position of the acyl oxonium is reported for C 2 -methylated pentoses, this phenomenon has already been described during the reaction of silyl enol ethers with peracylated- D -ribofuranose catalyzed by stannic chloride to produce C -nucleosides ( Yokoyama et al, 1982 ; Berber et al, 2001 ). Since then, a few other studies have reported this generally unexpected reactivity in C 2 -acylated sugars for other C -nucleophiles, such as allenyltributylstannane ( Chan et al, 2005 ), indium acetylenides ( Lubin-Germain et al, 2008 ), trimethylaluminum ( More and Campbell, 2009 ), cyanotrimethylsilane ( Popsavin et al, 2012 ), or zinc acetylenides ( Lemaire et al, 2014 ), suggesting that the small size of the nucleophile is the most decisive factor for the observed regioselectivity. The formation of the corresponding orthoesters is well known in the field of O -glycosylation, the latter serving as intermediates in the synthesis of oligosaccharides ( Kong, 2007 ).…”
Section: Resultsmentioning
confidence: 98%
“…Through the literary survey it became clear to us that many thiazole derivatives have an excellent anti-tumor activity as shown in Fig. 1 [22, 23]. In light of this, anti-tumor activity was examined for a new series of thiazole substitutes against breast cancer cells line (MCF-7).
Fig.
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Section: Resultsmentioning
confidence: 99%
“…Our literature survey showed that many thiazole and 1,3,4-thiadiazole derivatives have antitumor activity with excellent IG 50 and IC 50 values, as depicted in Figure 1 [55,56,57,58]. In view of these facts, we examined the antitumor activity of a new series of substituted thiadiazoles and thiazoles against the human breast carcinoma cell line (MCF-7) and against the human hepatocellular carcinoma (HepG2).…”
Section: Resultsmentioning
confidence: 99%