9-(2,3-Ο-isopropylidene-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine | 109680-74-2

• 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: 9-(2,3-Ο-isopropylidene-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine
• CAS: 109680-74-2
• 化学式: C₁₈H₂₅N₅O₄
• 分子量: 375.428
• InChiKey: GTDHWPUDMNPRAX-LSCFUAHRSA-N

物化性质

• 沸点：
  592.6±60.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  94.76
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  9-(2,3-Ο-isopropylidene-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine 在 硝酸 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到9-(2,3-O-isopropylidene-5-O-nitro-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine
  参考文献：
  名称：

  Discovery of 6-[4-(6-nitroxyhexanoyl)piperazin-1-yl)]-9H-purine, as pharmacological post-conditioning agent

  摘要：

  Novel purine analogues bearing nitrate esters were designed and synthesized in an effort to develop compounds triggering endogenous cardioprotective mechanisms such as ischemic preconditioning (IPC) or postconditioning (PostC). The majority of the compounds reduced infarct size compared to the control group in anesthetized rabbits, whereas administration of the most active analogue 16 at a dose of 3.8 mu mol/kg resulted on a significant reduction of infarct size, compared to PostC group (13.4 +/- 1.9% vs 26.4 +/- 2.3%). These findings introduce a novel class of promising pharmacological compounds that could be used as mimics or enhancers of PostC. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.037
• 作为产物：
  描述：

  6-哌啶嘌呤 在 硫酸氢铵 、 对甲苯磺酸一水合物 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 生成 9-(2,3-Ο-isopropylidene-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine
  参考文献：
  名称：

  Discovery of 6-[4-(6-nitroxyhexanoyl)piperazin-1-yl)]-9H-purine, as pharmacological post-conditioning agent

  摘要：

  Novel purine analogues bearing nitrate esters were designed and synthesized in an effort to develop compounds triggering endogenous cardioprotective mechanisms such as ischemic preconditioning (IPC) or postconditioning (PostC). The majority of the compounds reduced infarct size compared to the control group in anesthetized rabbits, whereas administration of the most active analogue 16 at a dose of 3.8 mu mol/kg resulted on a significant reduction of infarct size, compared to PostC group (13.4 +/- 1.9% vs 26.4 +/- 2.3%). These findings introduce a novel class of promising pharmacological compounds that could be used as mimics or enhancers of PostC. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.037

文献信息

• Studies on compounds related to antitumor agents. Syntheses of 8-substituted N6,N6-dimethyladenosine derivatives.
  作者：TETSUO KATO、EITARO ARAKAWA、SHUICHI OGAWA、YASUKO SUZUMURA、TAKETOSHI KATO

  DOI：10.1248/cpb.34.3635

  日期：——

  N6, N6-Dimethyl-8-methylsulfonyladenosine, obtained from N6, N6-dimethyl-8-methylthioadenosine by highly selective oxidation with KMnO4, was treated with cyanide ion to give 8-cyano-N6, N6-dimethyladenosine. The conversion of the cyano group to methyl imidate, methoxycarbonyl, carbamoyl, carbothioamide, and carboxylic acid moieties was achieved. These 8-substituted N6, N6-dimethyladenosines may possess resonances structures involving positions 6 and 8 in adenosine, as indicated by the spectroscopic data. They showed no antitumor activity.

  N6, N6-二甲基-8-甲磺酰基腺苷是通过 KMnO4 高选择性氧化从 N6, N6-二甲基-8-甲硫基腺苷中得到的，用氰离子处理得到 8-氰基-N6, N6-二甲基腺苷。氰基可转化为亚胺酸甲酯、甲氧基羰基、氨基甲酰基、硫代磷酸甲酰胺和羧酸分子。光谱数据表明，这些 8-取代的 N6、N6-二甲基腺苷可能具有涉及腺苷中第 6 和第 8 位的共振结构。它们没有显示出抗肿瘤活性。