5-cyano-2'-deoxycytidine | 1044575-52-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-cyano-2'-deoxycytidine
• 英文别名: 5-cyanodeoxycytidine；5-Cyano-2'-deoxycytidine；4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidine-5-carbonitrile
• CAS: 1044575-52-1
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: UUIDOCACRGIJJO-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-cyano-2'-deoxycytidine 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 4-N-acetyl-5-cyano-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine
  参考文献：
  名称：

  DNA双链体和形成三链体的寡脱氧核苷酸结合了修饰的核苷，形成稳定且选择性的三链体†

  摘要：

  我们以前曾报道过含有非天然碱基三联体G-PPI·C3的DNA三链体，其中 生产者价格指数 是吲哚融合的 胞嘧啶 衍生物掺入DNA双链体中，C3是由三聚体形成的三链体形成寡核苷酸（TFO）的无碱基位点 丙烯链接器。在这项研究中，我们开发了一个新的非自然基础三合会A-ψ·C R1，其中ψ和C R1 是基本部分 2'-脱氧伪神经杜里定 和5-取代的 脱氧胞苷， 分别。我们检查了R1的几个吸电子取代基，发现5-溴胞嘧啶 （碳溴）可以选择性地识别ψ。此外，我们开发了新的生产者价格指数 衍生物， PPI我，在吲哚环上具有一个甲基，以便在结合了各种Watson-Crick碱基对的DNA双链体之间实现选择性的三链体形成，例如 TA， CG， -， 和 G-PPI我以及包含T，C， 碳溴和C3。我们使用紫外熔融和凝胶迁移率迁移分析研究了这些双链体和TFO之间的选择性三链体形成。

  DOI：

  10.1039/c1ob06411h
• 作为产物：
  描述：

  3',5'-di-O-tert-butyldimethylsilyl-5-cyano-2'-deoxycytidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以64%的产率得到5-cyano-2'-deoxycytidine
  参考文献：
  名称：

  5-Modified-2′-dU and 2′-dC as Mutagenic Anti HIV-1 Proliferation Agents: Synthesis and Activity

  摘要：

  With the goal of limiting HIV-1 proliferation by increasing the mutation rate of the viral genome, we synthesized a series of pyrimidine nucleoside analogues modified in position 5 of the aglycone moiety but unmodified oil the sugar part. The synthetic strategies allow us to prepare the targeted compounds directly from commercially available nucleosides. All compounds were tested for their ability to reduce HIV-1 Proliferation in cell culture. Two of them (5-hydroxymethyl-2'-dU (1c) and 5-hydroxymethyl-2'-dC (2c)) displayed a moderate antiviral activity in single passage experiments. The same two compounds Plus two additional ones (5-carbamoyl-2'-dU (1a) and 5-carbamoylmethyl-2'-dU(1b)) were potent inhibitors of HIV-1 RT activity in serial passage assays, in which they induced a progressive loss of HIV-1 replication. In addition, viruses collected after seven passages in the presence of 1c and 2c replicated very poorly after withdrawal of these compounds, consistent with the accumulation of deleterious mutations in the HIV-1 genome.

  DOI：

  10.1021/jm901758f

文献信息

• DNA duplexes and triplex-forming oligodeoxynucleotides incorporating modified nucleosides forming stable and selective triplexes
  作者：Takashi Kanamori、Yoshiaki Masaki、Masahiro Mizuta、Hirosuke Tsunoda、Akihiro Ohkubo、Mitsuo Sekine、Kohji Seio

  DOI：10.1039/c1ob06411h

  日期：——

  an abasic site in triplex-forming oligonucleotides (TFOs) introduced by a propylene linker. In this study, we developed a new unnatural base triad A-ψ·CR1 where ψ and CR1 are base moieties 2′-deoxypseudouridine and 5-substituted deoxycytidine, respectively. We examined several electron-withdrawing substituents for R1 and found that 5-bromocytosine (CBr) could selectively recognize ψ. In addition, we

  我们以前曾报道过含有非天然碱基三联体G-PPI·C3的DNA三链体，其中 生产者价格指数 是吲哚融合的 胞嘧啶 衍生物掺入DNA双链体中，C3是由三聚体形成的三链体形成寡核苷酸（TFO）的无碱基位点 丙烯链接器。在这项研究中，我们开发了一个新的非自然基础三合会A-ψ·C R1，其中ψ和C R1 是基本部分 2'-脱氧伪神经杜里定 和5-取代的 脱氧胞苷， 分别。我们检查了R1的几个吸电子取代基，发现5-溴胞嘧啶 （碳溴）可以选择性地识别ψ。此外，我们开发了新的生产者价格指数 衍生物， PPI我，在吲哚环上具有一个甲基，以便在结合了各种Watson-Crick碱基对的DNA双链体之间实现选择性的三链体形成，例如 TA， CG， -， 和 G-PPI我以及包含T，C， 碳溴和C3。我们使用紫外熔融和凝胶迁移率迁移分析研究了这些双链体和TFO之间的选择性三链体形成。
• 5-Modified-2′-dU and 2′-dC as Mutagenic Anti HIV-1 Proliferation Agents: Synthesis and Activity
  作者：Yazan El Safadi、Jean-Christophe Paillart、Géraldine Laumond、Anne-Marie Aubertin、Alain Burger、Roland Marquet、Valérie Vivet-Boudou

  DOI：10.1021/jm901758f

  日期：2010.2.25

  With the goal of limiting HIV-1 proliferation by increasing the mutation rate of the viral genome, we synthesized a series of pyrimidine nucleoside analogues modified in position 5 of the aglycone moiety but unmodified oil the sugar part. The synthetic strategies allow us to prepare the targeted compounds directly from commercially available nucleosides. All compounds were tested for their ability to reduce HIV-1 Proliferation in cell culture. Two of them (5-hydroxymethyl-2'-dU (1c) and 5-hydroxymethyl-2'-dC (2c)) displayed a moderate antiviral activity in single passage experiments. The same two compounds Plus two additional ones (5-carbamoyl-2'-dU (1a) and 5-carbamoylmethyl-2'-dU(1b)) were potent inhibitors of HIV-1 RT activity in serial passage assays, in which they induced a progressive loss of HIV-1 replication. In addition, viruses collected after seven passages in the presence of 1c and 2c replicated very poorly after withdrawal of these compounds, consistent with the accumulation of deleterious mutations in the HIV-1 genome.