1-(3,5-dimethoxybenzyl)piperidin-4-amine | 380424-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(3,5-dimethoxybenzyl)piperidin-4-amine
• 英文别名: 4-amino-1-(3,5-dimethoxybenzyl)piperidine；1-[(3,5-dimethoxyphenyl)methyl]piperidin-4-amine
• CAS: 380424-81-7
• 化学式: C₁₄H₂₂N₂O₂
• mdl: MFCD10005765
• 分子量: 250.341
• InChiKey: WTBBUZDGTUDIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  47.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,5-dimethoxybenzyl)piperidin-4-amine 以 乙醇 为溶剂， 反应 24.0h， 生成 2-[trans-(4-aminocyclohexyl)amino]-6-[4-[1-(3,5-dimethoxybenzyl)]piperidinylamino]-9-cyclopentylpurine
  参考文献：
  名称：

  THE DESIGN AND SYNTHESIS OF PURINE INHIBITORS OF CDK2. III

  摘要：

  Cyclin-dependent kinases (CDKs) belong to a class of enzymes that control the ability of a cell to enter into and proceed through the cell division cycle. Using purine as a scaffold, we have synthesized a number of nanomolar inhibitors of CDK-2/cyclin E. In this report, the synthesis of a series of piperidine-substituted purine analogs will be presented, as well as some of their in vitro and in vivo biological effects.

  DOI：

  10.1081/ncn-100002493
• 作为产物：
  描述：

  1-[(3,5-Dimethoxyphenyl)methyl]piperidine-4-carboxamide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 乙腈 为溶剂， 生成 1-(3,5-dimethoxybenzyl)piperidin-4-amine
  参考文献：
  名称：

  THE DESIGN AND SYNTHESIS OF PURINE INHIBITORS OF CDK2. III

  摘要：

  Cyclin-dependent kinases (CDKs) belong to a class of enzymes that control the ability of a cell to enter into and proceed through the cell division cycle. Using purine as a scaffold, we have synthesized a number of nanomolar inhibitors of CDK-2/cyclin E. In this report, the synthesis of a series of piperidine-substituted purine analogs will be presented, as well as some of their in vitro and in vivo biological effects.

  DOI：

  10.1081/ncn-100002493

文献信息

• Synthesis, radiolabelling, and biodistribution studies of triazole derivatives for targeting melanoma
  作者：Stephanie M. Rathmann、Nancy Janzen、John F. Valliant

  DOI：10.1139/cjc-2016-0239

  日期：2016.9

  Molecular probes that target specific markers expressed in solid tumours are in demand for cancer imaging and radionuclide therapy applications. The synthesis, characterization, and in vivo evaluation of radioiodinated triazoles designed as probes to target melanoma are described here. Compounds were prepared using a thermal click reaction between ethynylstannane and methyl 2-azidoacetate, resulting in preferential formation of the corresponding 1,4-tin triazole. The primary amine of various targeting vectors was then coupled to the resulting tin triazole methyl ester. These precursors were labelled with no carrier added ¹²³I or ¹²⁵I and purified by high performance liquid chromatography to give isolated radiochemical yields between 6% and 51% and radiochemical purities of >95% in all cases. Among the evaluated compounds, N-(2-diethylamino-ethyl)-2-(4-iodo-[1,2,3]triazol-1-yl)acetamide (7a) and N-(1-benzylpiperidin-4-yl)-2-(4-iodo-1H-1,2,3-triazol-1-yl)acetamide (7d) showed the most promising in vivo data, and their ¹²³I-labelled forms were used in single photon emission computed tomography computed tomography (SPECT–CT) imaging studies. The imaging data showed excellent tumour visualization with a very high signal to noise ratio.

  靶向固体肿瘤中特定标记物的分子探针在癌症成像和放射性核素治疗应用中需求旺盛。本文描述了设计为靶向黑色素瘤的三唑类探针的合成、表征和体内评估的放射碘化合物。化合物是通过乙炔基锡烷和甲基2-叠氮乙酸酯之间的热点击反应制备的，导致了相应的1,4-锡三唑的优先形成。然后，各种靶向载体的主氨基与得到的锡三唑甲酯偶联。这些前体物质被标记为无载体添加的¹²³I或¹²⁵I，并通过高效液相色谱纯化，得到的分离放射化学产率在6%至51%之间，所有情况下的放射化学纯度均高于95%。在评估的化合物中，N-(2-二乙氨乙基)-2-(4-碘-[1,2,3]三唑-1-基)乙酰胺（7a）和N-(1-苄哌啶-4-基)-2-(4-碘-1H-1,2,3-三唑-1-基)乙酰胺（7d）展现出最有希望的体内数据，它们的¹²³I标记形式被用于单光子发射计算机断层扫描（SPECT-CT）成像研究。成像数据显示出优秀的肿瘤可视化效果，信噪比非常高。
• 6,9-disubstituted 2-[trans-(4-aminocyclohexyl) amino] purines
  申请人：——

  公开号：US20030105098A1

  公开（公告）日：2003-06-05

  The present invention comprises 6-9-Disubstituted 2-[trans-(4-aminocyclohexyl]aminopurines that are useful in inhibiting cyclin dependent kinases, particularly cdk-2. The present invention also provides a method of preventing apoptosis in neuronal cells and a method of inhibiting the development of neoplasms.

  本发明涉及6-9-二取代的2- [转-（4-氨基环己基）]氨基嘌呤，其在抑制细胞周期依赖性激酶，特别是cdk-2方面具有用途。本发明还提供了一种预防神经细胞凋亡和抑制肿瘤发展的方法。
• 6,9-DISUBSTITUTED 2- TRANS-(4- AMINOCYCLOHEXYL) AMINO]PURINES
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP1056744B1

  公开（公告）日：2003-10-22
• US6479487B1
  申请人：——

  公开号：US6479487B1

  公开（公告）日：2002-11-12
• US6642231B2
  申请人：——

  公开号：US6642231B2

  公开（公告）日：2003-11-04