5'-chloromercuri-2'-deoxycytidine | 65523-09-3

• 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'-chloromercuri-2'-deoxycytidine
• CAS: 65523-09-3
• 化学式: C₉H₁₂ClHgN₃O₄
• 分子量: 462.255
• InChiKey: POOYMQLJIODYGB-CDNBRZBRSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.67
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-chloromercuri-2'-deoxycytidine 在 lithium tetrachloropalladate 、 RhCl(PPh₃)3 、 copper dichloride 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 (E)-5-propenyl-2'-deoxycytidine
  参考文献：
  名称：

  Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity

  摘要：

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.

  DOI：

  10.1021/jm00363a009
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 以 水 为溶剂， 反应 20.0h， 生成 5'-chloromercuri-2'-deoxycytidine
  参考文献：
  名称：

  5-巯基胞嘧啶：一种有机金属的Janus核碱基

  摘要：

  已通过NMR滴定在单体水平上探索了5巯基胞嘧啶的碱基配对特性，并通过熔解温度测量在寡核苷酸上探索了5巯基胞嘧啶的碱基配对特性。NMR研究表明，它与鸟嘌呤，次黄嘌呤和尿苷具有相对较高的亲和力，也就是说，在Hg II配位时被去质子化的碱基。在寡核苷酸双链体中，5-巯基胞嘧啶与胸腺嘧啶和鸟嘌呤形成Hg II介导的碱基对。在前一种情况下，形成的双链体与仅包含Watson-Crick碱基对的双链体一样稳定。基于对熔解曲线的详细热力学分析，Hg II介导的碱基对的稳定可能归因于杂交的熵熵较低。

  DOI：

  10.1002/chem.201600851

文献信息

• Palladium-mediated synthesis of C-5 pyrimidine nucleoside thioethers from disulfides and mercurinucleosides
  作者：Donald E. Bergstrom、Peter Beal、Jeffrey Jenson、Xiaoping Lin

  DOI：10.1021/jo00019a025

  日期：1991.9

  Thioether-linked side chains can be created at C-5 of pyrimidine nucleosides via a palladium-mediated reaction of mercurated nucleosides with organic disulfides. 5-(Chloromercuri)-2'-deoxyuridine reacts with butyl disulfide, phenyl disulfide, dimethyl 3,3'-dithiodipropionate, and N,N'-bis(trifluoroacetyl)cystamine to yield respectively 5-(1-thiapentyl)-2'-deoxyuridine, 5-(phenylthio)-2'-deoxyuridine, 5-[3-(methoxycarbonyl)-1-thiapropyl]-2'-deoxyuridine, and 5-[3-(trifluoroacetamido)-1-thiapropyl]-2'-deoxyuridine in yields ranging from 46 to 73%. Other mercurated nucleosides, including 5-(chloromercuri)-2'-deoxycytidine, 5-(chloromercuri)cytidine, and 5-(chloromercuri)tubercidin react with N,N'-bis(trifluoroacetyl)cystamine and lithium-palladium chloride in methanol to yield the corresponding coupled products, but the yields are much lower (5-10%). The nucleoside coupling reaction is complicated by competing side reactions between disulfides and Pd2+, which remain to be elucidated.
• Hassan, Mohamed E., Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 6, p. 1295 - 1299
  作者：Hassan, Mohamed E.

  DOI：——

  日期：——
• C-5-Substituted pyrimidine nucleosides. 3. Reaction of allylic chlorides, alcohols, and acetates with pyrimidine nucleoside derived organopalladium intermediates
  作者：Donald E. Bergstrom、Jerry L. Ruth、Paul Warwick

  DOI：10.1021/jo00320a039

  日期：1981.3
• HASSAN, MOHAMED E., COLLECT. CZECHOSL. CHEM. COMMUN., 56,(1991) N, C. 1295-1299
  作者：HASSAN, MOHAMED E.

  DOI：——

  日期：——