(2S,3S,4R,5R)-3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide | 331729-03-4

• 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: (2S,3S,4R,5R)-3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide
• 英文别名: (2S,3S,4R,5R)-3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydrofuran-2-carboxylic acid methylamide；9-[2-O-acetyl-3-C-azido-3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl]-6-chloropurine；3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methyl amide；(2S,3S,4R,5R)3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide；(2S,3S,4R,5R)3-azido-5-(6-chloro-purin-9-yl)4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide；[(2R,3R,4S,5S)-4-azido-2-(6-chloropurin-9-yl)-5-(methylcarbamoyl)oxolan-3-yl] acetate
• CAS: 331729-03-4
• 化学式: C₁₃H₁₃ClN₈O₄
• 分子量: 380.75
• InChiKey: YCSDQGWMRRXTBL-GURMABIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide 在 甲醇 、 三乙胺 作用下， 反应 15.0h， 以77%的产率得到(2S,3S,4R,5R)-3-azido-5-(6-chloro-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide
  参考文献：
  名称：

  在人腺苷A3受体上合成的高效，选择性和水溶性激动剂。

  摘要：

  使用平行和定向合成的组合，发现了高效和选择性系列的腺苷A3激动剂。预期的肠胃外给药途径所需的高水溶性是通过存在一个或两个碱性胺官能团实现的。

  DOI：

  10.1016/j.bmcl.2006.01.088
• 作为产物：
  描述：

  双丙酮葡萄糖 在 ruthenium trichloride 吡啶 、 sodium periodate 、 sodium azide 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 过碘酸 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 、 水 、 溶剂黄146 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 89.0h， 生成 (2S,3S,4R,5R)-3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide
  参考文献：
  名称：

  3‘-Aminoadenosine-5‘-uronamides:  Discovery of the First Highly Selective Agonist at the Human Adenosine A₃ Receptor

  摘要：

  Selective adenosine A(3) agonists have potential utility for the prevention of perioperative myocardial ischemic injury. Herein, we report on the discovery and synthesis of compound 7. This amino nucleoside agonist possesses unprecedented levels of selectivity for the human adenosine A(3) receptor.

  DOI：

  10.1021/jm0255724

文献信息

• Compounds for the treatment of ischemia
  申请人：——

  公开号：US20040198693A1

  公开（公告）日：2004-10-07

  A 3 agonists, methods of using such A 3 agonists and pharmaceutical compositions containing such A 3 agonists. The A 3 agonists are useful for the reduction of tissue damage resulting from tissue ischemia or hypoxia.

  A3激动剂，使用此类A3激动剂的方法以及含有此类A3激动剂的药物组合物。这些A3激动剂对于减少由组织缺血或缺氧引起的组织损伤是有用的。
• HIV-integrase inhibitors, pharmaceutical compositions, and methods for their use
  申请人：Kuki Atsuo

  公开号：US20050165040A1

  公开（公告）日：2005-07-28

  Beta-carboline hydroxamic acid compounds represented by formula (I) are described. The beta-carboline hydroxamic acid compounds and compositions containing those compounds may be used to inhibit or modulate the activity of HIV integrase enzyme and to treat HIV integrase-mediated diseases and conditions.

  由公式（I）表示的β-咔啉羟肟酸化合物被描述。这些β-咔啉羟肟酸化合物和含有这些化合物的组合物可用于抑制或调节HIV整合酶酶的活性，并用于治疗HIV整合酶介导的疾病和症状。
• [EN] COMPOUNDS FOR THE TREATMENT OF ISCHEMIA<br/>[FR] COMPOSES DESTINES AU TRAITEMENT D'ISCHEMIE
  申请人：PFIZER PROD INC

  公开号：WO2001023399A1

  公开（公告）日：2001-04-05

  A3 agonists, methods of using such A3 agonists and pharmaceutical compositions containing such A3 agonists. The A3 agonists are useful for the reduction of tissue damage resulting from tissue ischemia or hypoxia.

  A3激动剂，使用这种A3激动剂的方法和含有这种A3激动剂的药物组合物。这些A3激动剂对于减少组织缺血或低氧引起的组织损伤非常有用。
• Purine derivatives for the treatment of ischemia
  申请人：Pfizer Products Inc.

  公开号：EP1241176A1

  公开（公告）日：2002-09-18

  A3 agonists having Formula I are described herein as well as methods of using such A3 agonists and pharmaceutical compositions containing such A3 agonists. The A3 agonists are useful for the reduction of tissue damage resulting from tissue ischemia or hypoxia.

  本文描述了具有式 I 的 A3 激动剂以及使用这种 A3 激动剂的方法和含有这种 A3 激动剂的药物组合物。 A3 激动剂可用于减少组织缺血或缺氧造成的组织损伤。
• Design and synthesis of 3′-ureidoadenosine-5′-uronamides: effects of the 3′-ureido group on binding to the A3 adenosine receptor
  作者：Lak Shin Jeong、Myong Jung Kim、Hea Ok Kim、Zhan-Guo Gao、Soo-Kyung Kim、Kenneth A. Jacobson、Moon Woo Chun

  DOI：10.1016/j.bmcl.2004.07.042

  日期：2004.10

  On the basis of high binding affinity at the A(3) adenosine receptor of 3'-aminoadenosine derivatives with hydrogen bonding donor ability, novel 3'-ureidoadenosine analogues were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose in order to lead to stronger hydrogen bonding than the corresponding 3'-aminoadeno sine derivatives. However, the synthesized 3'-ureidoadenosine analogues were totally devoid of binding affinity, because 3'-urea moiety caused steric and electrostatic repulsions at the binding site of the A(3) adenosine receptor, leading to conformational distortion. (C) 2004 Elsevier Ltd. All rights reserved.