(2S,3S,4R,5R)-2-[(1-methylimidazol-2-yl)sulfanylmethyl]-5-[6-[[(3R)-oxolan-3-yl]amino]purin-9-yl]oxolane-3,4-diol

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2S,3S,4R,5R)-2-[(1-methylimidazol-2-yl)sulfanylmethyl]-5-[6-[[(3R)-oxolan-3-yl]amino]purin-9-yl]oxolane-3,4-diol
• 化学式: C₁₈H₂₃N₇O₄S
• 分子量: 433.491
• InChiKey: MUQDCKYJVFVKKT-RSUGUSAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Tecadenoson 在 偶氮二甲酸二异丙酯 、 polystyrene bound triphenylphosphine 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (2S,3S,4R,5R)-2-[(1-methylimidazol-2-yl)sulfanylmethyl]-5-[6-[[(3R)-oxolan-3-yl]amino]purin-9-yl]oxolane-3,4-diol
  参考文献：
  名称：

  Structure–affinity relationships of 5 ′ -aromatic ethers and 5 ′ -aromatic sulfides as partial A 1 adenosine agonists, potential supraventricular anti-arrhythmic agents

  摘要：

  Atrial fibrillation (AF) is the most commonly encountered sustained clinical arrhythmia with an estimated 2.3 million cases in the US (2001). A, adenosine receptor agonists can slow the electrical impulse propagation through the atrioventricular (AV) node (i.e., negative dromotropic effect) resulting in prolongation of the stimulus-to-His bundle (S-H) interval to potentially reduce ventricular rate. Compounds that are full agonists of the A, adenosine receptor can cause high grade AV block. Therefore, it is envisioned that a compound that is a partial agonist of the A, adenosine receptor could avoid this deleterious effect. 5' Phenyl sulfides (e.g., 17, EC50 = 1.26 muM) and phenyl ethers (e.g., 28, EC50 = 0.2 muM) are partial agonists with respect to their AV nodal effects in guinea pig isolated hearts. Additional affinity, GTPgammaS binding data suggesting partial activity of the A(1) adenosine receptor, and PK results for 5' modified adenosine derivatives are shown. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.096

文献信息

• Structure–affinity relationships of 5 ′ -aromatic ethers and 5 ′ -aromatic sulfides as partial A 1 adenosine agonists, potential supraventricular anti-arrhythmic agents
  作者：Christopher F. Morrison、Elfatih Elzein、Bob Jiang、Prabha N. Ibrahim、Timothy Marquart、Venkata Palle、Kevin D. Shenk、Vaibhav Varkhedkar、Tenning Maa、Lin Wu、Yuzhi Wu、Dewan Zeng、Irving Fong、David Lustig、Kwan Leung、Jeff A. Zablocki

  DOI：10.1016/j.bmcl.2004.04.096

  日期：2004.7

  Atrial fibrillation (AF) is the most commonly encountered sustained clinical arrhythmia with an estimated 2.3 million cases in the US (2001). A, adenosine receptor agonists can slow the electrical impulse propagation through the atrioventricular (AV) node (i.e., negative dromotropic effect) resulting in prolongation of the stimulus-to-His bundle (S-H) interval to potentially reduce ventricular rate. Compounds that are full agonists of the A, adenosine receptor can cause high grade AV block. Therefore, it is envisioned that a compound that is a partial agonist of the A, adenosine receptor could avoid this deleterious effect. 5' Phenyl sulfides (e.g., 17, EC50 = 1.26 muM) and phenyl ethers (e.g., 28, EC50 = 0.2 muM) are partial agonists with respect to their AV nodal effects in guinea pig isolated hearts. Additional affinity, GTPgammaS binding data suggesting partial activity of the A(1) adenosine receptor, and PK results for 5' modified adenosine derivatives are shown. (C) 2004 Elsevier Ltd. All rights reserved.