(1aS,1bR,4aS,5R,5aS)-5-(2,6-Dichloro-purin-9-yl)-3,3-dimethyl-tetrahydro-2,4-dioxa-cyclopropa[a]pentalene-1a-carboxylic acid | 352552-15-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1aS,1bR,4aS,5R,5aS)-5-(2,6-Dichloro-purin-9-yl)-3,3-dimethyl-tetrahydro-2,4-dioxa-cyclopropa[a]pentalene-1a-carboxylic acid
• CAS: 352552-15-9
• 化学式: C₁₅H₁₄Cl₂N₄O₄
• 分子量: 385.207
• InChiKey: RFENISHITACJFL-QYZQZEHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.36
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1aS,1bR,4aS,5R,5aS)-5-(2,6-Dichloro-purin-9-yl)-3,3-dimethyl-tetrahydro-2,4-dioxa-cyclopropa[a]pentalene-1a-carboxylic acid 在 草酰氯 、 TEA 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Ring-Constrained (N)-Methanocarba nucleosides as adenosine receptor agonists: independent 5′-Uronamide and 2′-deoxy modifications

  摘要：

  Novel methanocarba adenosine analogues, having the pseudo-ribose northern (N) conformation preferred at adenosine receptors (ARs), were synthesized and tested in binding assays. The 5'-uronamide modification preserved [N-6-(3-iodobenzyl)] or enhanced (N-6-methyl) affinity at A(3)ARs, while the 2'-deoxy modification reduced affinity and efficacy in a functional assay. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00213-x
• 作为产物：
  描述：

  (1R,2R,3S,4R,5S)-4-(2,6-dichloropurin-9-yl)-1-hydroxymethyl-2,3-O-isopropylidenebicyclo[3.1.0]hexane 在 ruthenium(IV) oxide 、 sodium periodate 、 potassium carbonate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 24.0h， 以97.3%的产率得到(1aS,1bR,4aS,5R,5aS)-5-(2,6-Dichloro-purin-9-yl)-3,3-dimethyl-tetrahydro-2,4-dioxa-cyclopropa[a]pentalene-1a-carboxylic acid
  参考文献：
  名称：

  Ring-Constrained (N)-Methanocarba nucleosides as adenosine receptor agonists: independent 5′-Uronamide and 2′-deoxy modifications

  摘要：

  Novel methanocarba adenosine analogues, having the pseudo-ribose northern (N) conformation preferred at adenosine receptors (ARs), were synthesized and tested in binding assays. The 5'-uronamide modification preserved [N-6-(3-iodobenzyl)] or enhanced (N-6-methyl) affinity at A(3)ARs, while the 2'-deoxy modification reduced affinity and efficacy in a functional assay. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00213-x