Methyl 4-ethynyl-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]pentoxy]benzoate | 801240-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 4-ethynyl-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]pentoxy]benzoate
• CAS: 801240-08-4
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: BFDAVAFBWYMYTK-UHFFFAOYSA-N

物化性质

• 沸点：
  501.9±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-ethynyl-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]pentoxy]benzoate 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 Methyl 4-[2-[6-(methylamino)pyridin-2-yl]ethyl]-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]pentoxy]benzoate
  参考文献：
  名称：

  Chemical Adaptor Immunotherapy:  Design, Synthesis, and Evaluation of Novel Integrin-Targeting Devices

  摘要：

  A series of beta-diketone derivatives of RGD peptidornimetics that selectively bind to alphabbeta3 and alphavbeta5 integrins were synthesized and covalently docked to the reactive lysine residues of monoclonal aldolase antibody 38C2. The resulting targeting devices strongly and selectively bound to human cancer cells expressing integrins alphavbeta3 and alphavbeta5 as analyzed by flow cytometry. In vitro and in vivo studies revealed that these novel integrin-targeting devices efficiently inhibit tumor growth. Thus, the combination of beta-diketone derivatives of RGD peptidomimetics that target cell surface integrins alphavbeta3 and alphavbeta5 with monoclonal aldolase antibodies through formation of a covalent bond of defined stoichiometry holds promise as a new approach to cancer therapy.

  DOI：

  10.1021/jm049666k
• 作为产物：
  描述：

  5-(N-叔丁氧羰基氨基)-1-戊醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 Methyl 4-ethynyl-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]pentoxy]benzoate
  参考文献：
  名称：

  Chemical Adaptor Immunotherapy:  Design, Synthesis, and Evaluation of Novel Integrin-Targeting Devices

  摘要：

  A series of beta-diketone derivatives of RGD peptidornimetics that selectively bind to alphabbeta3 and alphavbeta5 integrins were synthesized and covalently docked to the reactive lysine residues of monoclonal aldolase antibody 38C2. The resulting targeting devices strongly and selectively bound to human cancer cells expressing integrins alphavbeta3 and alphavbeta5 as analyzed by flow cytometry. In vitro and in vivo studies revealed that these novel integrin-targeting devices efficiently inhibit tumor growth. Thus, the combination of beta-diketone derivatives of RGD peptidomimetics that target cell surface integrins alphavbeta3 and alphavbeta5 with monoclonal aldolase antibodies through formation of a covalent bond of defined stoichiometry holds promise as a new approach to cancer therapy.

  DOI：

  10.1021/jm049666k