4-(丙-2-炔-1-基氧基)苄基氨基甲酸叔丁酯 | 1380401-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(丙-2-炔-1-基氧基)苄基氨基甲酸叔丁酯
• 英文名称: tert-butyl N-{[4-(prop-2-yn-1-yloxy)phenyl]methyl}carbamate
• 英文别名: tert-butyl (4-(prop-2-yn-1-yloxy)benzyl)carbamate；Carbamic acid, N-[[4-(2-propyn-1-yloxy)phenyl]methyl]-, 1,1-dimethylethyl ester；tert-butyl N-[(4-prop-2-ynoxyphenyl)methyl]carbamate
• CAS: 1380401-33-1
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: PIGAXXGRAFGNBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(丙-2-炔-1-基氧基)苄基氨基甲酸叔丁酯 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以86%的产率得到(4-(prop-2-yn-1-yloxy)phenyl)methanamine
  参考文献：
  名称：

  Radiolabeled Selective Matrix Metalloproteinase 13 (MMP-13) Inhibitors: (Radio)Syntheses and in Vitro and First in Vivo Evaluation

  摘要：

  The noninvasive imaging of MMP activity in vivo could have a high impact in basic research as well as in clinical applications. This approach can be established using radiolabeled MMP inhibitors (MMPIs) as tracers for the detection of activated MMPs by means Of PET. However, the complexity of diseases associated with dysregulated MMP expression necessitates the imaging of distinct MMPs or MMP subgroups to distinguish their individual role in specific diseases. To this end, selective and potent MMP-13 inhibitors based on a N, N'-bis(benzyppyrimidine-4,6-dicarboxamide core have been synthesized and successfully radiolabeled with carbon-11, fluorine-18, and gallium-68. Selected radiolabeled candidates were evaluated in-vitro and in vivo regarding their pharmacokinetic properties and metabolic stability.

  DOI：

  10.1021/acs.jmedchem.6b01284
• 作为产物：
  描述：

  4-羟基苄胺溴酸盐 在 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 、 乙腈 为溶剂， 反应 23.0h， 生成 4-(丙-2-炔-1-基氧基)苄基氨基甲酸叔丁酯
  参考文献：
  名称：

  Structure-Based Design of Type II Inhibitors Applied to Maternal Embryonic Leucine Zipper Kinase

  摘要：

  A novel Type II kinase inhibitor chemotype has been identified for maternal embryonic leucine zipper kinase (MELK) using structure-based ligand design. The strategy involved structural characterization of an induced DFG-out pocket by proteinligand X-ray crystallography and incorporation of a slender linkage capable of bypassing a large gate-keeper residue, thus enabling design of molecules accessing both hinge and induced pocket regions. Optimization of an initial hit led to the identification of a low-nanomolar, cell-penetrant Type II inhibitor suitable for use as a chemical probe for MELK.

  DOI：

  10.1021/ml5001273

文献信息

• A Rotaxane-Based Switchable Organocatalyst
  作者：Victor Blanco、Armando Carlone、Kevin D. Hänni、David A. Leigh、Bartosz Lewandowski

  DOI：10.1002/anie.201201364

  日期：2012.5.21

  Switch it on! The activity of an organocatalytic group incorporated within a rotaxane architecture can be controlled by switching the position of the macrocycle. The system was used to mediate the progress of the Michael addition of an aliphatic thiol to trans‐cinnamaldehyde.

  把它打开！可以通过切换大环的位置来控制引入轮烷结构中的有机催化基团的活性。该系统用于介导将脂肪族硫醇迈克尔加成反式肉桂醛的过程。
• Radiolabeled Selective Matrix Metalloproteinase 13 (MMP-13) Inhibitors: (Radio)Syntheses and in Vitro and First in Vivo Evaluation
  作者：Verena Hugenberg、Stefan Wagner、Klaus Kopka、Michael Schäfers、Robert C. Schuit、Albert D. Windhorst、Sven Hermann

  DOI：10.1021/acs.jmedchem.6b01284

  日期：2017.1.12

  The noninvasive imaging of MMP activity in vivo could have a high impact in basic research as well as in clinical applications. This approach can be established using radiolabeled MMP inhibitors (MMPIs) as tracers for the detection of activated MMPs by means Of PET. However, the complexity of diseases associated with dysregulated MMP expression necessitates the imaging of distinct MMPs or MMP subgroups to distinguish their individual role in specific diseases. To this end, selective and potent MMP-13 inhibitors based on a N, N'-bis(benzyppyrimidine-4,6-dicarboxamide core have been synthesized and successfully radiolabeled with carbon-11, fluorine-18, and gallium-68. Selected radiolabeled candidates were evaluated in-vitro and in vivo regarding their pharmacokinetic properties and metabolic stability.
• Structure-Based Design of Type II Inhibitors Applied to Maternal Embryonic Leucine Zipper Kinase
  作者：Christopher N. Johnson、Christophe Adelinet、Valerio Berdini、Lijs Beke、Pascal Bonnet、Dirk Brehmer、Frederick Calo、Joseph E. Coyle、Phillip J. Day、Martyn Frederickson、Eddy J. E. Freyne、Ron A. H. J. Gilissen、Christopher C. F. Hamlett、Steven Howard、Lieven Meerpoel、Laurence Mevellec、Rachel McMenamin、Elisabeth Pasquier、Sahil Patel、David C. Rees、Joannes T. M. Linders

  DOI：10.1021/ml5001273

  日期：2015.1.8

  A novel Type II kinase inhibitor chemotype has been identified for maternal embryonic leucine zipper kinase (MELK) using structure-based ligand design. The strategy involved structural characterization of an induced DFG-out pocket by proteinligand X-ray crystallography and incorporation of a slender linkage capable of bypassing a large gate-keeper residue, thus enabling design of molecules accessing both hinge and induced pocket regions. Optimization of an initial hit led to the identification of a low-nanomolar, cell-penetrant Type II inhibitor suitable for use as a chemical probe for MELK.