Methyl-carbamic acid (3aR,4R,6R,6aR)-2,2-dimethyl-6-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester | 342419-08-3

• 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: Methyl-carbamic acid (3aR,4R,6R,6aR)-2,2-dimethyl-6-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
• CAS: 342419-08-3
• 化学式: C₁₉H₂₆N₆O₆
• 分子量: 434.452
• InChiKey: DANVSKQXTYWCCZ-RSUGUSAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  130.88
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Methyl-carbamic acid (3aR,4R,6R,6aR)-2,2-dimethyl-6-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 在 溶剂黄146 作用下， 生成 CVT-2759
  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
• 作为产物：
  描述：

  Tecadenoson 在 对甲苯磺酸 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 Methyl-carbamic acid (3aR,4R,6R,6aR)-2,2-dimethyl-6-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  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