Synthesis of 2'-methylene-substituted 5-azapyrimidine, 6-azapyrimidine, and 3-deazaguanine nucleoside analogues as potential antitumor/antiviral agents

Article abstract of DOI:10.1080/07328319908045594

2'-Deoxy-2'-methylene-6-azauridine (5) and 2'-deoxy-2'-methylene-6- azacytidine (8) have been synthesized via a multi-step procedure from 6- azauridine. 2'-Deoxy-2'-methylene-5-azacytidine (14a) and 2'-deoxy-2'- methylene-3-deazaguanosine (19a) and their corresponding α-anomers (14b and 19b) have been synthesized by the transglycosylation of 3',5'-O-(1,1,3,3- tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-methyleneuridine (12) with silylated 5-azacytosine and silylated N²-palmitoyl-3-deazaguanine, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst in anhydrous dichloroethane, followed by separation of the isomers and deprotection of the blocking groups. These compounds were tested for cytotoxicity against B₁₆F₁₀, L1210, and CCRF-CEM tumor cell lines and for antiviral activity against HIV-1, HSV-1, and HSV-2.

Full text of DOI:10.1080/07328319908045594

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Synthesis of 2′-Methylene-Substituted 5-
Azapyrimidine, 6-Azapyrimidine, and 3-
Deazaguanine Nucleoside Analogues as
Potential Antitumor/Antiviral Agents
Mao-Chin Liu a , Mei-Zhen Luo a , Diane E. Mozdziesz a , Tai-Shun Lin
a , Ginger E. a , Dutschman 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: 04 Oct 2006.
To cite this article: Mao-Chin Liu , Mei-Zhen Luo , Diane E. Mozdziesz , Tai-Shun Lin , Ginger E. ,
Dutschman , Yung-Chi Cheng & Alan C. Sartorelli (1999) Synthesis of 2′-Methylene-Substituted 5-
Azapyrimidine, 6-Azapyrimidine, and 3-Deazaguanine Nucleoside Analogues as Potential Antitumor/
Antiviral Agents, Nucleosides and Nucleotides, 18:1, 55-72, DOI: 10.1080/07328319908045594
To link to this article: http://dx.doi.org/10.1080/07328319908045594
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