C3-Paullone | 362029-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: C3-Paullone
• 英文别名: 3-(4-aminobutoxy)-9-bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one；5-(4-Aminobutoxy)-14-bromo-8,18-diazatetracyclo[9.7.0.0;{2,7}.0;{12,17}]octadeca-1(11),2,4,6,12(17),13,15-heptaen-9-one hydrochloride；3-(4-aminobutoxy)-9-bromo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
• CAS: 362029-07-0
• 化学式: C₂₀H₂₀BrN₃O₂
• 分子量: 414.302
• InChiKey: MAQBOTRSBYDGOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  C3-Paullone 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-甲基吡咯烷酮 作用下， 反应 10.0h， 生成 3-[4-(biotinylamido)-butoxy]-9-bromo-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one
  参考文献：
  名称：

  通过聚合物辅助溶液相合成对胺进行生物素标记。

  摘要：

  已经开发出一种有效且简单的聚合物辅助方法来生物素化带有氨基官能团的多功能化合物。生物素通过Kenner安全捕捉连接器固定在氨基甲基化的聚苯乙烯上，被激活并随后通过化学选择性转移至目标化合物的氨基官能团，从而避免了保护基团的作用。这种方法具有引入间隔物修饰的生物素衍生物的潜力。

  DOI：

  10.1016/s0960-894x(01)00296-7
• 作为产物：
  描述：

  9-Bromo-3-methoxypaullone 在 三溴化硼 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 C3-Paullone
  参考文献：
  名称：

  Synthesis of Paullones with Aminoalkyl Side Chains

  摘要：

  Paullones 3 and 4 with aminoalkyl side chains in 2- or 3-position were synthesized as derivatives of kenpaullone 1. Both 3 and 4 showed the characteristic CDK1-inhibitory activity of the paullones and a modest antiproliferative activity on cultured human tumor cell lines. Hence, 3 and 4 appear to be suitable tools for affinity studies directed to find additional intracellular paullone targets.

  DOI：

  10.1002/1521-4184(200209)335:7<311::aid-ardp311>3.0.co;2-f

文献信息

• Polymer-bound reagents for the introduction of spacer-modified biotin labels
  作者：Claudia Herforth、Philipp Heidler、Stephan Franke、Andreas Link

  DOI：10.1016/j.bmc.2004.03.038

  日期：2004.6

  We have developed a method for the chemoselective introduction of spacer modified biotin labels into unprotected multifunctional amines. A range of novel biotin spacer conjugates attached to a polymer-bound sulfonamide anchor was prepared using established amide bond forming procedures. After chemical transformation of the attachment site by alkylation, the resulting reactive species were utilized as N-selective polymer-supported biotinylation reagents. The labeled compounds, obtained in good to excellent yield and purity, are free of residual biotin and possess a custom tailored distance from the immobilization site being especially suited for the immobilization on streptavidin-functionalized dextran layers of surface plasmon resonance detector chips. In addition, derivatives displaying a phenyl group were synthesized in order to demonstrate the versatility of the procedure for the simultaneous introduction of spacer-modified biotin and a UV-light absorbing moiety. The formation of biotin sulfoxides in the presence of in situ generated peroxides was investigated and is discussed. Our results suggest that this derivatization technique is a useful addition to the existing biotin labeling protocols. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of Paullones with Aminoalkyl Side Chains
  作者：Karen Wieking、Marie Knockaert、Maryse Leost、Daniel W. Zaharevitz、Laurent Meijer、Conrad Kunick

  DOI：10.1002/1521-4184(200209)335:7<311::aid-ardp311>3.0.co;2-f

  日期：2002.9

  Paullones 3 and 4 with aminoalkyl side chains in 2- or 3-position were synthesized as derivatives of kenpaullone 1. Both 3 and 4 showed the characteristic CDK1-inhibitory activity of the paullones and a modest antiproliferative activity on cultured human tumor cell lines. Hence, 3 and 4 appear to be suitable tools for affinity studies directed to find additional intracellular paullone targets.
• Biotin labelling of amines by polymer-assisted solution-phase synthesis
  作者：Abolfasl Golisade、Claudia Herforth、Karen Wieking、Conrad Kunick、Andreas Link

  DOI：10.1016/s0960-894x(01)00296-7

  日期：2001.7

  multifunctional compounds bearing an amino functionality. Biotin was immobilized on aminomethylated polystyrene via the Kenner safety catch linker, activated and subsequently transferred to the amino function of the target compounds chemoselectively, thus avoiding protecting group operations. This approach holds potential for the introduction of spacer-modified biotin derivatives.

  已经开发出一种有效且简单的聚合物辅助方法来生物素化带有氨基官能团的多功能化合物。生物素通过Kenner安全捕捉连接器固定在氨基甲基化的聚苯乙烯上，被激活并随后通过化学选择性转移至目标化合物的氨基官能团，从而避免了保护基团的作用。这种方法具有引入间隔物修饰的生物素衍生物的潜力。