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

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

Gang Guo 1 email, Gang Li 1 email, Dan Liu 1 email, Qian-Jiao Yang 1 email, Yu Liu 1 email, Yong-Kui Jing 2 email and Lin-Xiang Zhao 1,* email
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; in revised form: 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.

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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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