(E)-5-(2-Carboxyvinyl)-2'-deoxycytidin | 74131-07-0

• 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: (E)-5-(2-Carboxyvinyl)-2'-deoxycytidin
• 英文别名: (E)-5-(2-carboxyvinyl)-2'-deoxycytidine；3-[4-amino-1-(β-D-erythro-2-deoxy-pentofuranosyl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-acrylic acid；E-5-(2-carboxyvinyl)-2'-deoxycytidine；(E)-3-[4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-5-yl]prop-2-enoic acid
• CAS: 74131-07-0
• 化学式: C₁₂H₁₅N₃O₆
• 分子量: 297.268
• InChiKey: JEEPLDNEMJPHTF-PIXDULNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-dibutylformamide dimethyl acetal 、 (E)-5-(2-Carboxyvinyl)-2'-deoxycytidin 以 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到(E)-5-(2-carboxyvinyl)-4-N-(N',N'-di(n-butyl)formamidine)-2'-deoxycytidine
  参考文献：
  名称：

  Doubly thiazole orange-labeled cytidine for functional expansion of a hybridization-sensitive probe

  摘要：

  A 2'-deoxycytidine derivative modified by two thiazole orange dyes has been designed for functional expansion of hybridization-sensitive fluorescence probes. This nucleotide was synthesized by a procedure that included protection of the cytosine amino group by di(n-butyl)formamidine formation, followed by incorporation into DNA. The fluorescence of the synthesized DNA was controlled by excitonic interaction, showing strong fluorescence upon hybridization with the target nucleic acid and effective quenching in a single-stranded state of the probe. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.037
• 作为产物：
  描述：

  methyl 3-(2'-deoxy-5-cytidinyl)propenoate 在 水 、 sodium hydroxide 作用下， 反应 2.0h， 以91%的产率得到(E)-5-(2-Carboxyvinyl)-2'-deoxycytidin
  参考文献：
  名称：

  Doubly thiazole orange-labeled cytidine for functional expansion of a hybridization-sensitive probe

  摘要：

  A 2'-deoxycytidine derivative modified by two thiazole orange dyes has been designed for functional expansion of hybridization-sensitive fluorescence probes. This nucleotide was synthesized by a procedure that included protection of the cytosine amino group by di(n-butyl)formamidine formation, followed by incorporation into DNA. The fluorescence of the synthesized DNA was controlled by excitonic interaction, showing strong fluorescence upon hybridization with the target nucleic acid and effective quenching in a single-stranded state of the probe. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.037

文献信息

• E-5-(2-Halogenovinyl)-2'-deoxycytidines
  申请人：The University of Birmingham

  公开号：US04382925A1

  公开（公告）日：1983-05-10

  The invention relates to E-5-(2-halogenovinyl)-2'-deoxycytidines, e.g. E-5-(bromovinyl)-2'-deoxycytidine and E-5-(2-iodovinyl)-2'-deoxycytidine. These substances are endowed with specific antiviral activities towards herpes simplex virus and with an extremely low toxicity which makes them useful in antiviral medicines and for treatment of virus diseases in man and animal. They may be synthesized by introduction of an E-5-(2-halogenovinyl) sidechain into 2'-deoxycytidine, or by condensation of a trialkylsilyl derivative of E-5-(2-halogenovinyl)-cytosine with a hydroxyl-protected reactive derivative of 2'-deoxy-D-erythro-pentofuranose.

  本发明涉及E-5-(2-卤代乙烯基)-2'-脱氧胞苷，例如E-5-(溴乙烯基)-2'-脱氧胞苷和E-5-(2-碘乙烯基)-2'-脱氧胞苷。这些物质具有对单纯疱疹病毒的特异性抗病毒活性，并具有极低的毒性，使它们有用于抗病毒药物和治疗人和动物病毒性疾病。它们可以通过将E-5-(2-卤代乙烯基)侧链引入2'-脱氧胞苷中合成，或通过将E-5-(2-卤代乙烯基)-胞嘧啶的三烷基硅基衍生物与2'-脱氧-D-核糖呋喃糖的羟基保护反应衍生物缩合而制备。
• US4382925A
  申请人：——

  公开号：US4382925A

  公开（公告）日：1983-05-10
• Doubly thiazole orange-labeled cytidine for functional expansion of a hybridization-sensitive probe
  作者：Shuji Ikeda、Mizue Yuki、Hiroyuki Yanagisawa、Akimitsu Okamoto

  DOI：10.1016/j.tetlet.2009.10.037

  日期：2009.12

  A 2'-deoxycytidine derivative modified by two thiazole orange dyes has been designed for functional expansion of hybridization-sensitive fluorescence probes. This nucleotide was synthesized by a procedure that included protection of the cytosine amino group by di(n-butyl)formamidine formation, followed by incorporation into DNA. The fluorescence of the synthesized DNA was controlled by excitonic interaction, showing strong fluorescence upon hybridization with the target nucleic acid and effective quenching in a single-stranded state of the probe. (c) 2009 Elsevier Ltd. All rights reserved.