2-Chloro-purine riboside | 5466-11-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-Chloro-purine riboside
• 英文别名: (2R,3R,4S,5R)-2-(2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；2-Cl-nebularine；(1R)-1-(2-chloro-purin-9-yl)-D-1,4-anhydro-ribitol；(1R)-1-(2-Chlor-purin-9-yl)-D-1,4-anhydro-ribit；(2R,3R,4S,5R)-2-(2-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 5466-11-5
• 化学式: C₁₀H₁₁ClN₄O₄
• 分子量: 286.675
• InChiKey: DXGGYSNDZSUEHC-JXOAFFINSA-N

物化性质

• 熔点：
  154-156 °C(Solv: water (7732-18-5))
• 沸点：
  580.9±60.0 °C(Predicted)
• 密度：
  2.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Chloro-purine riboside 在 palladium on activated charcoal 、 水 作用下， 生成 9 - (Β-D -呋喃核糖)嘌呤
  参考文献：
  名称：

  Synthesis of Potential Anticancer Agents. XV. Ribonucleosides of 2-Substituted Purines

  摘要：

  DOI：

  10.1021/ja01551a033
• 作为产物：
  描述：

  (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 在 氨 作用下， 以 乙醇 、 氯仿 为溶剂， 以204 mg的产率得到2-Chloro-purine riboside
  参考文献：
  名称：

  Investigations into the Origin of the Molecular Recognition of Several Adenosine Deaminase Inhibitors

  摘要：

  Inhibitors of adenosine deaminase (ADA, EC 3 5 4 4) are potential therapeutic agents for the treatment of various health disorders Several highly potent inhibitors were previously identified, yet they exhibit unacceptable toxicities We performed a SAR study involving a series of C2 or C8 substituted purine-riboside analogues with a view to discover less potent inhibitors with a lesser toxicity We found that any substitution at C8 position of nebularine resulted in total loss of activity toward calf intestinal ADA However several 2-substituted-adenosine, 8-aza-adenosine, and nebularine analogues exhibited inhibitory activity Specifically, 2-Cl-purine riboside, 8-aza-2-thiohexyl adenosine, 2-thiohexyl adenosine, and 2-MeS-purine riboside were found to be competitive inhibitors of ADA with K-i values of 25, 22, 6, and 3 mu M, respectively We concluded that electronic parameters are not major recognition determinants of ADA but rather steric parameters A C2 substituent which fits ADA hydrophobic pocket and improves H-bonding with the enzyme makes a good inhibitor In addition, a gg rotamer about C4'-C5' bond is apparently an important recognition determinant

  DOI：

  10.1021/jm101286g

文献信息

• Novel adenosine derivatives and pharmaceutical compositions containing them as an active ingredient
  申请人：NIPPON ZOKI PHARMACEUTICAL CO. LTD.

  公开号：EP0269574A2

  公开（公告）日：1988-06-01

  The present invention relates to novel adenosine derivatives having the formula (I): wherein each of R₁, R₂ and R₃, which may be the same or different, is hydrogen or a lower alkyl group; X is hydrogen, a lower alkyl group, an amino group or halogen; and Y is hydrogen or a lower alkyl group; and pharmaceutically acceptable salt thereof. These compounds are useful as antihypertensive agents, for example, for the treatments of hypertension and various diseases caused by hypertension, such as cerebrovascular diseases, cardiopathy or renal insufficiency.

  本发明涉及具有式(I)的新型腺苷衍生物：其中，R₁、R₂和R₃可以相同或不同，各自为氢或低级烷基；X为氢、低级烷基、氨基或卤素；Y为氢或低级烷基；及其药学上可接受的盐。 这些化合物可用作降压药，例如，用于治疗高血压和高血压引起的各种疾病，如脑血管疾病、心脏病或肾功能不全。
• Investigations into the Origin of the Molecular Recognition of Several Adenosine Deaminase Inhibitors
  作者：Irina Gillerman、Bilha Fischer

  DOI：10.1021/jm101286g

  日期：2011.1.13

  Inhibitors of adenosine deaminase (ADA, EC 3 5 4 4) are potential therapeutic agents for the treatment of various health disorders Several highly potent inhibitors were previously identified, yet they exhibit unacceptable toxicities We performed a SAR study involving a series of C2 or C8 substituted purine-riboside analogues with a view to discover less potent inhibitors with a lesser toxicity We found that any substitution at C8 position of nebularine resulted in total loss of activity toward calf intestinal ADA However several 2-substituted-adenosine, 8-aza-adenosine, and nebularine analogues exhibited inhibitory activity Specifically, 2-Cl-purine riboside, 8-aza-2-thiohexyl adenosine, 2-thiohexyl adenosine, and 2-MeS-purine riboside were found to be competitive inhibitors of ADA with K-i values of 25, 22, 6, and 3 mu M, respectively We concluded that electronic parameters are not major recognition determinants of ADA but rather steric parameters A C2 substituent which fits ADA hydrophobic pocket and improves H-bonding with the enzyme makes a good inhibitor In addition, a gg rotamer about C4'-C5' bond is apparently an important recognition determinant
• Synthesis of Potential Anticancer Agents. XV. Ribonucleosides of 2-Substituted Purines
  作者：Howard J. Schaeffer、H. Jeanette Thomas

  DOI：10.1021/ja01551a033

  日期：1958.9