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

被引：7
|
作者：
Liu, MC
Luo, MZ
Mozdziesz, DE
Lin, TS
Dutschman, GE
Cheng, YC
Sartorelli, AC [1 ]
机构：
[1] Yale Univ, Sch Med, Ctr Canc, Dept Pharmacol, New Haven, CT 06520 USA
[2] Yale Univ, Sch Med, Ctr Canc, Dev Therapeut Sect, New Haven, CT 06520 USA
来源：
NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 01期
关键词：
D O I：
10.1080/07328319908045594
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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 a-anomers (14b and 19b) have been synthesized by the transglycosylation of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-2'-deoxy-2'-methyleneuridine (12) with silylated 5-azacytosine and silylated N-2-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.
引用
收藏
页码：55 / 72
页数：18
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