6-(piperidin-1-yl)-9-(tetrahydropyran-2-yl)purine | 446832-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-(piperidin-1-yl)-9-(tetrahydropyran-2-yl)purine
• 英文别名: 9-(Oxan-2-yl)-6-piperidin-1-ylpurine
• CAS: 446832-13-9
• 化学式: C₁₅H₂₁N₅O
• 分子量: 287.365
• InChiKey: LVJMTYWNCMAFIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(piperidin-1-yl)-9-(tetrahydropyran-2-yl)purine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 N-(2-hydroxyethyl)-6-(piperidin-1-yl)-9-(tetrahydropyran-2-yl)-purine-8-carboxamide
  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：

  哌啶 、 6-氯-9-(四氢-2-吡喃基)嘌呤 在 三乙胺 作用下， 以 丙醇 为溶剂， 反应 3.0h， 以85%的产率得到6-(piperidin-1-yl)-9-(tetrahydropyran-2-yl)purine
  参考文献：
  名称：

  6-取代的嘌呤作为具有抗转移活性的ROCK抑制剂。

  摘要：

  Rho相关的丝氨酸/苏氨酸激酶（ROCKs）是肌动蛋白细胞骨架的主要调节剂，可调节细胞的收缩性，形状，运动性和侵袭性。我们探索了在一组碳素原子上被哌啶-1-基或氮杂-1-基取代的嘌呤衍生物的结构与抗ROCK2活性之间的关系。结构活性关系（SAR）分析表明，通过在C2原子处取代母体化合物或通过扩展C6侧链，可以保留抗ROCK活性，并且可以进一步提高抗ROCK活性。这些ROCK抑制剂可以在细胞内达到有效浓度，这可以通过ROCK靶MLC磷酸化的减少以及抑制ROCK依赖的黑色素瘤细胞在胶原蛋白基质中的侵入来证明。

  DOI：

  10.1016/j.bioorg.2019.103005

文献信息

• 6-Substituted purines as ROCK inhibitors with anti-metastatic activity
  作者：Jiří Voller、Lenka Zahajská、Lucie Plíhalová、Jana Jeřábková、David Burget、Andreea Csilla Pataki、Vladimír Kryštof、Marek Zatloukal、Jan Brábek、Daniel Rösel、Václav Mik、Martin Tkáč、Tomáš Pospíšil、Tomáš Gucký、Karel Doležal、Miroslav Strnad

  DOI：10.1016/j.bioorg.2019.103005

  日期：2019.9

  contractility, shape, motility, and invasion of cells. We explored the relationships between structure and anti-ROCK2 activity in a group of purine derivatives substituted at the C6 atom by piperidin-1-yl or azepan-1-yl groups. Structure-activity relationship (SAR) analyses suggested that anti-ROCK activity is retained, and may be further increased, by substitution of the parent compounds at the C2 atom or by expansion

  Rho相关的丝氨酸/苏氨酸激酶（ROCKs）是肌动蛋白细胞骨架的主要调节剂，可调节细胞的收缩性，形状，运动性和侵袭性。我们探索了在一组碳素原子上被哌啶-1-基或氮杂-1-基取代的嘌呤衍生物的结构与抗ROCK2活性之间的关系。结构活性关系（SAR）分析表明，通过在C2原子处取代母体化合物或通过扩展C6侧链，可以保留抗ROCK活性，并且可以进一步提高抗ROCK活性。这些ROCK抑制剂可以在细胞内达到有效浓度，这可以通过ROCK靶MLC磷酸化的减少以及抑制ROCK依赖的黑色素瘤细胞在胶原蛋白基质中的侵入来证明。
• Discovery of 6-[4-(6-nitroxyhexanoyl)piperazin-1-yl)]-9H-purine, as pharmacological post-conditioning agent
  作者：Maria Koufaki、Theano Fotopoulou、Efstathios K. Iliodromitis、Sophia-Iris Bibli、Anastasia Zoga、Dimitrios Th. Kremastinos、Ioanna Andreadou

  DOI：10.1016/j.bmc.2012.07.037

  日期：2012.10

  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.