Synthesis and biological evaluation of 1,3-oxathiolane 5-azapyrimidine, 6-azapyrimidine, and fluorosubstituted 3-deazapyrimidine nucleosides

Article abstract of DOI:10.1080/15257770008035011

(2R,5S)-5-Amino-2-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2,4- triazine-3(2H)-one (8) and (2R,5R)-5-amino-2-[2-(hydroxymethyl)-1,3- oxathiolan-5-yl]-1,2,4-triazine-3(2H)-one (9) have been synthesized via a multi-step procedure from 6-azauridine. (2R,5S)-4-Amino-1-[2-(hydroxymethyl)- 1, 3-oxathiolan-5-yl]-1,3,5-triazine-2(1H)-one (11) and (2R,5R)-4-amino-1-[2- (hydroxymethyl)-1,3-oxathiolan-5-yl]-1,3,5-triazine-2(1H)-one (12), and the fluorosubstituted 3-deazanucleosides (19-24) have been synthesized by the transglycosylation of (2R,5S)-1-{2-[[(tert-butyldiphenylsilyl) oxy]methyl]- 1,3-oxathiolan-5-yl}cytosine (2) with silylated 5-azacytosine and the corresponding silylated fluorosubstituted 3-deazacytosines, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst in anhydrous dichloroethane, followed by deprotection of the blocking groups. These compounds were tested in vitro for cytotoxicity against L1210, B₁₆F₁₀, and CCRF-CEM tumor cell lines and for antiviral activity against HIV-1 and HBV.

Full text of DOI:10.1080/15257770008035011

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Synthesis and Biological Evaluation of
1,3-Oxathiolane 5-Azapyrimidine, 6-
Azapyrimidine, and Fluorosubstituted 3-
Deazapyrimidine Nucleosides
Mao-Chin Liu a , Mei-Zhen Luo a , Diane E. Mozdziesz a , Tai-Shun Lin
a , Ginger E. Dutschman a , Elizabeth A. Gullen a , Yung-Chi Cheng a
& Alan C. Sartorelli a
a Department of Pharmacology and Developmental Therapeutics
Section , Cancer Center, Yale University School of Medicine , New
Haven, Connecticut, 06520-8066, USA
Published online: 24 Sep 2006.
To cite this article: Mao-Chin Liu , Mei-Zhen Luo , Diane E. Mozdziesz , Tai-Shun Lin , Ginger
E. Dutschman , Elizabeth A. Gullen , Yung-Chi Cheng & Alan C. Sartorelli (2000) Synthesis and
Biological Evaluation of 1,3-Oxathiolane 5-Azapyrimidine, 6-Azapyrimidine, and Fluorosubstituted
3-Deazapyrimidine Nucleosides, Nucleosides, Nucleotides and Nucleic Acids, 19:3, 603-618, DOI:
10.1080/15257770008035011
To link to this article: http://dx.doi.org/10.1080/15257770008035011
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