Synthesis and antiproliferative activities of 5-azacytidine analogues in human leukemia cells.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Gang GuoLin-xiang Zhao

Abstract

Twenty-six 5-azacytidine analogues have been synthesized, including 4-amino- 6-alkyl-1-pyranosyl/ribofuranosyl-1,3,5-triazin-2(1H)-ones 1a-j, 6-amino-4-alkyl/aryl-1- pyranosyl/ribofuranosyl-1,3,5-triazin-2(1H)-ones 2a-f and 4-amino-6-alkyl-1,3,5-triazin-2- yl-1-thio-pyranosides/ribofuranosides 3a-j. The antiproliferative activities of these synthetic analogues were investigated in human leukemia HL-60 cells. Ribofuranosyl S-nucleoside 3a, a bioisostere of 5-azacytidine, had a similar antiproliferative ability as that of the latter. Introduction of a methyl at the 6 position of 5-azacytidine and/or replacement of the ribofuranosyl moiety with pyranosyl sugars or disaccharides significantly decreased the antiproliferative activities of the 5-azacytidine derivatives. Several compounds with the replacement of pyranosyl sugars enhanced all-trans retinoic acid-induced differentiation ability in human leukemia HL-60 cells.

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Citations

Jun 3, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Cornelia VetterDirk Steinborn
Sep 8, 2011·Proceedings of the National Academy of Sciences of the United States of America·Christina L GardnerWilliam B Klimstra
Jun 8, 2012·Proceedings of the National Academy of Sciences of the United States of America·David M RosmarinHidde L Ploegh
Aug 1, 2013·Proceedings of the National Academy of Sciences of the United States of America·Fen TianDong Zhang
Nov 13, 2009·The Journals of Gerontology. Series A, Biological Sciences and Medical Sciences·Michal M MasternakAdam Spong
Dec 14, 2011·The Journals of Gerontology. Series A, Biological Sciences and Medical Sciences·Juan DingJohn J Kopchick
Jul 10, 2012·Glycobiology·Vaibhav TiwariDeepak Shukla
Apr 2, 2014·The Journal of Cell Biology·Madhurima DharaDieter Bruns

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Methods Mentioned

BETA
MDS
column chromatography
glycosylation

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