C-5-bromo-2'-deoxycytidine | 102871-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: C-5-bromo-2'-deoxycytidine
• CAS: 102871-24-9
• 化学式: C₁₀H₁₄BrN₃O₃
• 分子量: 304.143
• InChiKey: QFCPVEHWUKYIRB-VMHSAVOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  101.37
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  Acetic acid (1R,2S,4S)-2-acetoxymethyl-4-(4-amino-5-bromo-2-oxo-2H-pyrimidin-1-yl)-cyclopentyl ester 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 C-5-bromo-2'-deoxycytidine
  参考文献：
  名称：

  Carbocyclic analogs of 5-halocytosine nucleosides

  摘要：

  Carbocyclic analogues of 5-halocytosine nucleosides were prepared by direct halogenation of the carbocyclic analogues of cytidine, 2'-deoxycytidine, 3'-deoxycytidine, or ara-C. The 5-chloro and 5-bromo derivatives of the cytidine (carbodine) and of the 2'-deoxycytidine analogues and the 5-iodo derivatives of all four of the cytosine nucleoside analogues were prepared. All of the C-5-halocytosine nucleosides, as well as the parent C-cytosine nucleosides, were tested against a strain of herpes simplex virus type 1 (HSV-1) that induces thymidine kinase in host cells. Carbodine, 5-bromocarbodine, C-2'-deoxycytidine, C-5-bromo-2'-deoxycytidine, the four C-5-iodocytosine nucleosides, and C-ara-C inhibited replication of this strain of HSV-1 in cultured cells. Most of these compounds were tested also against the type 2 virus (HSV-2) in vitro and were active. The greatest activity observed was exerted by C-5-iodo-2'-deoxycytidine in inhibiting replication of HSV-1 in L929 cells. In tests against these DNA viruses, carbodine, a ribofuranoside analogue that had been shown previously to be highly active against human influenza A virus in vitro, was the most active compound against HSV-2 and one of the most active compounds against HSV-1 in Vero cells. 5-Bromocarbodine was active against influenza virus, but it was less active than carbodine.

  DOI：

  10.1021/jm00159a026