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

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

Received: 20 June 2008; in revised form: 15 July 2008 / Accepted: 15 July 2008 / Published: 23 July 2008
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.
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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.

AMA 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(7):1487-1500.

Chicago/Turabian Style

Guo, Gang; Li, Gang; Liu, Dan; Yang, Qian-Jiao; Liu, Yu; Jing, Yong-Kui; Zhao, Lin-Xiang. 2008. "Synthesis and Antiproliferative Activities of 5-Azacytidine Analogues in Human Leukemia Cells." Molecules 13, no. 7: 1487-1500.

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