7-[(2-acetoxyethoxy)methyl]-4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine | 120386-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-[(2-acetoxyethoxy)methyl]-4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine
• 英文别名: 4-amino-6-bromo-5-cyano-7-<(2-acetoxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine；2-[(4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl acetate
• CAS: 120386-03-0
• 化学式: C₁₂H₁₂BrN₅O₃
• 分子量: 354.163
• InChiKey: HTGURYMSECCEOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  116.05
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  7-[(2-acetoxyethoxy)methyl]-4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine 在 溶剂黄146 、 sodium nitrite 、 水 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 18.0h， 以91%的产率得到7-[(2-acetoxyethoxy)methyl]-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Acyclic Sugar Analogs of Triciribine: Lack of Antiviral and Antiproliferative Activity Correlate with Low Intracellular Phosphorylation

  摘要：

  Triciribine and triciribine monophosphate have antiviral and antiproliferative activity at low or submicromolar concentrations. In an effort to improve and better understand this activity, we have synthesized a series of acyclic analogs and evaluated them for activity against select viruses and cancer cell. lines. We conclude that the rigid ribosyl ring system of triciribine must be intact in order to be phosphorylated and to obtain significant antiviral and antiproliferative activity.

  DOI：

  10.1080/07328319908044621
• 作为产物：
  描述：

  乙酸酐 、 4-amino-6-bromo-5-cyano-7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine 在 吡啶 作用下， 反应 24.0h， 以88%的产率得到7-[(2-acetoxyethoxy)methyl]-4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Acyclic Sugar Analogs of Triciribine: Lack of Antiviral and Antiproliferative Activity Correlate with Low Intracellular Phosphorylation

  摘要：

  Triciribine and triciribine monophosphate have antiviral and antiproliferative activity at low or submicromolar concentrations. In an effort to improve and better understand this activity, we have synthesized a series of acyclic analogs and evaluated them for activity against select viruses and cancer cell. lines. We conclude that the rigid ribosyl ring system of triciribine must be intact in order to be phosphorylated and to obtain significant antiviral and antiproliferative activity.

  DOI：

  10.1080/07328319908044621

文献信息

• Synthesis, cytotoxicity, and antiviral activity of certain 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine nucleosides related to toyocamycin and sangivamycin
  作者：Pranab K. Gupta、M. Reza Nassiri、Lisa A. Coleman、Linda L. Wotring、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jm00127a003

  日期：1989.7

  7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine derivatives related to the nucleoside antibiotics toyocamycin and sangivamycin were prepared and tested for their biological activity. Treatment of the sodium salt of 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine (1) with (2-acetoxyethoxy)methyl bromide (2) afforded a mixture of 4-amino-6-bromo-5-cyano-7-[(2-acetoxyethoxy)methyl]pyrrolo[2,3-d] pyrimidine

  制备了许多与核苷抗生素Toyocamycin和Sangivamycin有关的7-[（（2-羟基乙氧基）甲基]吡咯并[2,3-d]嘧啶衍生物，并对其生物学活性进行了测试。用（2-乙酰氧基乙氧基）甲基溴（2）处理4-氨基-6-溴-5-氰基吡咯并[2,3-d]嘧啶（1）的钠盐，得到4-氨基-6-溴的混合物-5-氰基-7-[（2-乙酰氧基乙氧基）甲基]吡咯并[2,3-d]嘧啶（3）和相应的N1异构体。将该混合物脱溴，得到相应的4-氨基-5-氰基-7-[（2-乙酰氧基乙氧基）-甲基]吡咯并[2，3-d]嘧啶（4）和4-氨基-5-氰基-1- [（2-乙酰氧基乙氧基）甲基]吡咯并[2,3-d]嘧啶e（5）。4和5的脱乙酰基分别提供4-氨基-5-氰基-7-[（2-羟基乙氧基）甲基]吡咯并[2，3-d]嘧啶（6）和相应的N1异构体（7）。基于UV光谱研究和13 C NMR光谱，指定了6和7的无环部分的连接位
• GUPTA, PRANAB K.;NASSIRI, M. REZA;COLEMAN, LISA A.;WOTRING, LINDA L.;DRAC+, J. MED. CHEM., 32,(1989) N, C. 1420-1425
  作者：GUPTA, PRANAB K.、NASSIRI, M. REZA、COLEMAN, LISA A.、WOTRING, LINDA L.、DRAC+

  DOI：——

  日期：——