(1S,2R,5R)-5-(6-chloropurin-9-yl)-3-(2-hydroxyethyl)cyclopent-3-ene-1,2-diol | 1373313-88-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1S,2R,5R)-5-(6-chloropurin-9-yl)-3-(2-hydroxyethyl)cyclopent-3-ene-1,2-diol
• 英文别名: (1S,2R,5S) 5-(6-chloropurine-9-yl)-3-hydroxyethylcyclopent-3-en-1,2-diol
• CAS: 1373313-88-2
• 化学式: C₁₂H₁₃ClN₄O₃
• 分子量: 296.713
• InChiKey: ZPRRNSHEPGFCCC-QNSHHTMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  104.29
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R)-5-(6-chloropurin-9-yl)-3-(2-hydroxyethyl)cyclopent-3-ene-1,2-diol 在 氨 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以67%的产率得到homoneplanocin A
  参考文献：
  名称：

  立体选择性合成氟代人单胞菌素A作为潜在的抗病毒药

  摘要：

  氟homoneplanocin A（4）由合成d -核糖，经由的烯炔闭环复分解9，环氧化物的立体选择性开口23a中被氟，和一个同时氧化消除反应。关键中间体8有望用作合成核苷的通用中间体。

  DOI：

  10.1021/ol300667q
• 作为产物：
  描述：

  6-氯嘌呤 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 (1S,2R,5R)-5-(6-chloropurin-9-yl)-3-(2-hydroxyethyl)cyclopent-3-ene-1,2-diol
  参考文献：
  名称：

  Structure–Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities

  摘要：

  On the basis of the potent inhibitory activity of neplanocin A (1) against S-adenosylhomocysteine (AdoHcy) hydrolase, we analyzed the comprehensive structure-activity relationships by modifying the adenine and carbasugar moiety of 1 to find the pharmacophore in the active site of the enzyme. The introduction of 7-deazaadenine instead of adenine eliminated the inhibitory activity against the AdoHcy hydrolase, while 3-deazaadenine maintained the inhibitory activity of the enzyme, indicating that N-7 is essential for its role as a hydrogen bonding acceptor. The substitution of hydrogen at the 6'-position with fluorine increased the inhibitory activity Of the enzyme. The one-carbon homologation at the 5'-position generally decreased the inhibitory activity of the enzyme, indicating that steric repulsion exists. A molecular docking study also supported these experimental data. In this study, 6'-fluoroneplanocin A (2) was the most potent inhibitor of AdoHcy hydrolase (IC50 = 0.24 mu M). It showed a potent anti-VSV activity (EC50 = 0.43 mu M) and potent anticancer activity in all the human tumor cell lines tested.

  DOI：

  10.1021/acs.jmedchem.5b00553