4-[6-(3-{2-[2-(3-tert-Butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-propylamino)-pyridin-2-ylethynyl]-benzoic acid ethyl ester | 801240-17-5

• 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: 4-[6-(3-{2-[2-(3-tert-Butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-propylamino)-pyridin-2-ylethynyl]-benzoic acid ethyl ester
• 英文别名: Ethyl 4-[2-[6-[3-[2-[2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propoxy]ethoxy]ethoxy]propylamino]pyridin-2-yl]ethynyl]benzoate
• CAS: 801240-17-5
• 化学式: C₃₁H₄₃N₃O₇
• 分子量: 569.698
• InChiKey: MSFQXIZBFRGAPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  41
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[6-(3-{2-[2-(3-tert-Butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-propylamino)-pyridin-2-ylethynyl]-benzoic acid ethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 32.0h， 生成 4-{2-[6-(3-{2-[2-(3-tert-Butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-propylamino)-pyridin-2-yl]-ethyl}-benzoic acid
  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：

  4-乙炔苯甲酸乙酯 、 [3-(2-{2-[3-(6-Bromo-pyridin-2-ylamino)-propoxy]-ethoxy}-ethoxy)-propyl]-carbamic acid tert-butyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 various solvent(s) 为溶剂， 反应 16.0h， 以77%的产率得到4-[6-(3-{2-[2-(3-tert-Butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-propylamino)-pyridin-2-ylethynyl]-benzoic acid ethyl ester
  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