92952-40-4

Usage

InChI:InChI=1/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5+,6-,7-/m1/s1

Upstream product

• 1409941-12-3 C₂₇H₂₅NO₉S 
• 60084-10-8 tiazofurin 
• 92952-39-1 Acetic acid (2R,3S,4R,5R)-5-(4-carbamoyl-thiazol-2-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 
• 92982-23-5 Trifluoro-methanesulfonic acid (2R,3R,4S,5R)-5-(4-carbamoyl-thiazol-2-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 
• 92952-38-0 2-[(2R,3R,4R,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-thiazole-4-carboxylic acid amide 
• 92952-37-9 2-[(2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-thiazole-4-carboxylic acid amide 
• 92952-36-8 2-[(2R,3S,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-thiazole-4-carboxylic acid amide 
• 92516-87-5 3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)tiazofurin 

Relevant academic research and scientific papers

Structure based design, synthesis and in vitro antitumour activity of tiazofurin stereoisomers with nitrogen functions at the C-2′ or C-3′ positions

Three novel tiazofurin analogues having D-arabino stereochemistry and nitrogen functionalities at the C-2′ position (5–7) have been designed and synthesized in multistep sequences, starting from D-glucose. The known D-xylo stereoisomer of 1 (compound 2) a

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

2-(β-d-xylofuranosyl)thiazole-4-carboxamide (2) and two new tiazofurin analogues with 5-hydroxymethyl-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol moiety as a sugar mimic (27 and 28) have been synthesized and evaluated for their in vitro antitumour activity against a panel of human tumour cell lines (K562, HL 60, Jurkat, Raji and HeLa). In contrast to previous literature reports, a metabolic MTT assay revealed remarkable cytotoxicity of 2 against K562 (IC50 = 0.15 μM) and HL-60 (IC50 = 0.13 μM) cells. Flow cytometry data suggest that cytotoxic effects of analogue 2 in the culture of K562 cells might be mediated by apoptosis, in opposite to tiazofurin, which did not induce apoptosis of K562 cells after 24 h, thus suggesting a different mechanism of action. All three analogues 2, 27 and 28 were also active against Jurkat, Raji and HeLa cells, with IC50 values in the range from 0.06 to 5.61 μM, but were completely inactive against the normal foetal lung fibroblasts (MRC-5).

SYNTHESIS OF 2-&β-D-ARA- AND 2-&β-D-XYLOFURANOSYLTHIAZOLE-4-CARBOXAMIDE

The syntheses of the heretofore unknown 2-β-D-ara and 2-β-D-xylofuranosyl isomers of the antitumor agent tiazofurin have been accomplished.In both cases the stereospecific inversion of the required 2' or 3'-hydroxyl group in the protected parent compound