2-cyclohexyl-N-(1-(hex-5-yn-1-yl)piperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-amine | 1586014-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-cyclohexyl-N-(1-(hex-5-yn-1-yl)piperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-amine
• CAS: 1586014-83-6
• 化学式: C₃₃H₄₉N₅O₂
• 分子量: 547.784
• InChiKey: VRDAQZLWDFZTMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  62.75
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-cyclohexyl-N-(1-(hex-5-yn-1-yl)piperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-amine 、 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以74%的产率得到
  参考文献：
  名称：

  Membrane-Permeant, Environment-Sensitive Dyes Generate Biosensors within Living Cells

  摘要：

  Dyes with environment-sensitive fluorescence have proven useful to study the spatiotemporal dynamics of protein activity in living cells. When attached to proteins, their fluorescence can reflect protein conformational changes, post-translational modifications, or protein interactions. However, the utility of such dye-protein conjugates has been limited because it is difficult to load them into cells. They usually must be introduced using techniques that perturb cell physiology, limit throughput, or generate fluorescent vesicles (e.g., electroporation, microinjection, or membrane transduction peptides). Here we circumvent these problems by modifying a proven, environment-sensitive biosensor fluorophore so that it can pass through cell membranes without staining intracellular compartments and can be attached to proteins within living cells using unnatural amino acid (UAA) mutagenesis. Reactive groups were incorporated for attachment to UAAs or small molecules (mero166, azide; mero167, alkyne; mero76, carboxylic acid). These dyes are bright and fluoresce at long wavelengths (reaching epsilon = 100 000 M-1 cm(-1), phi = 0.24, with excitation 565 nm and emission 594 nm). The utility of mero166 was demonstrated by in-cell labeling of a UAA to generate a biosensor for the small GTPase Cdc42. In addition, conjugation of mero166 to a small molecule produced a membrane-permeable probe that reported the localization of the DNA methyltransferase G9a in cells. This approach provides a strategy to access biosensors for many targets and to more practically harness the varied environmental sensitivities of synthetic dyes.

  DOI：

  10.1021/jacs.8b09841
• 作为产物：
  描述：

  5-甲氧基-2-硝基-4-(3-(吡咯烷-1-基)丙氧基)苯甲酸甲酯 在 盐酸 、 ammonium acetate 、 铁粉 、 potassium carbonate 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-cyclohexyl-N-(1-(hex-5-yn-1-yl)piperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolin-4-amine
  参考文献：
  名称：

  赖氨酸甲基转移酶 G9a 体外和体内沉淀的化学工具

  摘要：

  在这里，我们报告了一种新化学工具 UNC0965 的设计、合成和生化表征。UNC0965 是我们之前报道的 G9a 化学探针 UNC0638 的生物素化版本。重要的是，UNC0965 保持高体外效力并且是细胞渗透性的。UNC0965 的生物素化标签能够从全细胞裂解物中“化学沉淀”G9a。此外，UNC0965 的细胞外显率使我们能够通过基于化学抑制剂的染色质免疫沉淀（chem-ChIP）在体外和体内探索 G9a 在染色质上的定位。

  DOI：

  10.1002/cmdc.201300450