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Molecules 2008, 13(7), 1487-1500; doi:10.3390/molecules13071487

Synthesis and Antiproliferative Activities of 5-Azacytidine Analogues in Human Leukemia Cells

1
Shenyang Pharmaceutical University, Shenyang, 110016, P. R. China
2
Mount Sinai School of Medicine, One Gustave L. Levy Place, New York, NY 10029, USA
*
Author to whom correspondence should be addressed.
Received: 20 June 2008 / Revised: 15 July 2008 / Accepted: 15 July 2008 / Published: 23 July 2008
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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 Snucleoside 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.
Keywords: 5-Azacytidine analogues; antiproliferative activity; differentiation; leukemia; structure-activity relationship. 5-Azacytidine analogues; antiproliferative activity; differentiation; leukemia; structure-activity relationship.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Guo, G.; Li, G.; Liu, D.; Yang, Q.-J.; Liu, Y.; Jing, Y.-K.; Zhao, L.-X. Synthesis and Antiproliferative Activities of 5-Azacytidine Analogues in Human Leukemia Cells. Molecules 2008, 13, 1487-1500.

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