Next Article in Journal
Synthesis and Antimicrobial Activity of Some New Pyrazole, Fused Pyrazolo[3,4-d]-pyrimidine and Pyrazolo[4,3-e][1,2,4]- triazolo[1,5-c]pyrimidine Derivatives
Previous Article in Journal
Facile Synthesis of Oleanolic Acid Monoglycosides and Diglycosides
Molecules 2008, 13(7), 1487-1500; doi:10.3390/molecules13071487
Article

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

1
,
1
,
1
,
1
,
1
,
2
 and
1,*
Received: 20 June 2008 / Revised: 15 July 2008 / Accepted: 15 July 2008 / Published: 23 July 2008
Download PDF [280 KB, uploaded 18 June 2014]

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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert