2-{6-[((3R)oxolan-3-yl)amino]purin-9-yl}(4S,2R,3R,5R)-5-{[(dimethylamino)thioxomethoxy]methyl}oxolane-3,4-diol

• 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-{6-[((3R)oxolan-3-yl)amino]purin-9-yl}(4S,2R,3R,5R)-5-{[(dimethylamino)thioxomethoxy]methyl}oxolane-3,4-diol
• 英文别名: O-[[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-[[(3R)-oxolan-3-yl]amino]purin-9-yl]oxolan-2-yl]methyl] N,N-dimethylcarbamothioate
• 化学式: C₁₇H₂₄N₆O₅S
• 分子量: 424.481
• InChiKey: HWUKZZRTOQAPGE-ZGOQAQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  159
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Tecadenoson 在 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 57.0h， 生成 2-{6-[((3R)oxolan-3-yl)amino]purin-9-yl}(4S,2R,3R,5R)-5-{[(dimethylamino)thioxomethoxy]methyl}oxolane-3,4-diol
  参考文献：
  名称：

  Affinity and intrinsic efficacy (IE) of 5′-carbamoyl adenosine analogues for the A1 adenosine receptor—efforts towards the discovery of a chronic ventricular rate control agent for the treatment of atrial fibrillation (AF)

  摘要：

  The SAR for the affinity to the A, adenosine receptor and relative intrinsic efficacy (IE, [S-35]-GTPgammaS binding) of a series of 5'-carbamate and 5'-thionocarbamate derivatives of tecadenoson is described. Based on this SAR, selected compounds were evaluated in guinea pig isolated hearts to determine whether they were partial or full agonists with respect to their negative dromotropism, an A(1) AdoR mediated effect. Progress towards obtaining a partial A(1) AdoR agonist to potentially control ventricular rate during atrial fibrillation has been made with the discovery of several potent partial A(1) AdoR agonists (compounds 13, 14, and 17). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.094

文献信息

• Method of identifying partial adenosine A1 receptor agonists and their use in the treatment of arrhythmias
  申请人：——

  公开号：US20010008883A1

  公开（公告）日：2001-07-19

  The present invention provides a method for identifying parital adenosine A1 receptor agonists that are useful in the treatment of arrhythmias. Partial adenosine A1 receptor agonists and methods for using partial adenosine A1 receptor agonists to treat arrhythmias in mammals.

  本发明提供了一种用于识别对治疗心律失常有用的部分腺苷A1受体激动剂的方法。部分腺苷A1受体激动剂以及使用部分腺苷A1受体激动剂治疗哺乳动物心律失常的方法。
• N6 heterocyclic 5' modified adenosine derivatives
  申请人：CV Therapeutics, Inc.

  公开号：US20020037872A1

  公开（公告）日：2002-03-28

  N 6 heterocyclic 5′ modified adenosine derivatives that are adenosine A 1 receptor partial or full agonists, and as such, are useful for modifying cardiac activity, modifying adipocyte function, treating central nervous system disorders, and treating diabetic disorders and obesity in mammals, and especially in humans.

  N6杂环5'-修饰腺苷衍生物是腺苷A1受体的部分或全激动剂，因此对于修饰心脏活动、修饰脂肪细胞功能、治疗中枢神经系统疾病、治疗哺乳动物的糖尿病和肥胖症，特别是人类，具有用途。
• US6258793B1
  申请人：——

  公开号：US6258793B1

  公开（公告）日：2001-07-10
• US6576620B2
  申请人：——

  公开号：US6576620B2

  公开（公告）日：2003-06-10
• Affinity and intrinsic efficacy (IE) of 5′-carbamoyl adenosine analogues for the A1 adenosine receptor—efforts towards the discovery of a chronic ventricular rate control agent for the treatment of atrial fibrillation (AF)
  作者：Venkata P Palle、Vaibhav Varkhedkar、Prabha Ibrahim、Hiba Ahmed、Zhihe Li、Zhenhai Gao、Mark Ozeck、Yuzhi Wu、Dewan Zeng、Lin Wu、Kwan Leung、Nancy Chu、Jeff A Zablocki

  DOI：10.1016/j.bmcl.2003.09.094

  日期：2004.1

  The SAR for the affinity to the A, adenosine receptor and relative intrinsic efficacy (IE, [S-35]-GTPgammaS binding) of a series of 5'-carbamate and 5'-thionocarbamate derivatives of tecadenoson is described. Based on this SAR, selected compounds were evaluated in guinea pig isolated hearts to determine whether they were partial or full agonists with respect to their negative dromotropism, an A(1) AdoR mediated effect. Progress towards obtaining a partial A(1) AdoR agonist to potentially control ventricular rate during atrial fibrillation has been made with the discovery of several potent partial A(1) AdoR agonists (compounds 13, 14, and 17). (C) 2003 Elsevier Ltd. All rights reserved.