2-chloro-2'-ethoxy-5'-isopropyl-3,7'-biquinoline | 1415663-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-chloro-2'-ethoxy-5'-isopropyl-3,7'-biquinoline
• 英文别名: 7-(2-Chloroquinolin-3-yl)-2-ethoxy-5-propan-2-ylquinoline；7-(2-chloroquinolin-3-yl)-2-ethoxy-5-propan-2-ylquinoline
• CAS: 1415663-45-4
• 化学式: C₂₃H₂₁ClN₂O
• 分子量: 376.886
• InChiKey: GLUWGGVPSOWYTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-2'-ethoxy-5'-isopropyl-3,7'-biquinoline 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 水 、 sodium carbonate 、 氯化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 21.33h， 生成 2-Ethoxy-5-propan-2-yl-3-(5-propan-2-yl-2-propoxyquinolin-7-yl)-7-(2-pyrrolidin-1-ylquinolin-3-yl)quinoline
  参考文献：
  名称：

  Synthesis and biological activities of polyquinoline derivatives: New Bcl-2 family protein modulators

  摘要：

  The synthesis of quinoline derivatives, designed to interact with BCl-x(L), and to inhibit its interaction with pro-apoptotic partners, is described and their biological effects investigated. We showed that 5 out of 28 synthetized compounds restored cell death of 3T3 cells overexpressing Bcl-x(L) following serum starvation. Active compounds were further characterized for their binding capacity to the anti-apoptotic member of the Bcl-2 family, Bcl-x(L) as well as Bcl-2, Bcl-x(L) and Mcl-1, and for their pro-apoptotic activities toward lymphoid tumor cells and peripheral blood mononuclear cells. Altogether our results indicate that dimeric, rather than trimeric quinoline derivatives, represent a new attractive class of BH3 mimetics for cancer therapy. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.012
• 作为产物：
  描述：

  2-氯喹啉-3-硼酸 、 7-bromo-2-ethoxy-5-isopropylquinoline 在 三叔丁基膦 、 palladium diacetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以57%的产率得到2-chloro-2'-ethoxy-5'-isopropyl-3,7'-biquinoline
  参考文献：
  名称：

  Synthesis and biological activities of polyquinoline derivatives: New Bcl-2 family protein modulators

  摘要：

  The synthesis of quinoline derivatives, designed to interact with BCl-x(L), and to inhibit its interaction with pro-apoptotic partners, is described and their biological effects investigated. We showed that 5 out of 28 synthetized compounds restored cell death of 3T3 cells overexpressing Bcl-x(L) following serum starvation. Active compounds were further characterized for their binding capacity to the anti-apoptotic member of the Bcl-2 family, Bcl-x(L) as well as Bcl-2, Bcl-x(L) and Mcl-1, and for their pro-apoptotic activities toward lymphoid tumor cells and peripheral blood mononuclear cells. Altogether our results indicate that dimeric, rather than trimeric quinoline derivatives, represent a new attractive class of BH3 mimetics for cancer therapy. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.012

文献信息

• Synthesis and biological activities of polyquinoline derivatives: New Bcl-2 family protein modulators
  作者：Emmanuelle Saugues、Anne-Laure Debaud、Fabrice Anizon、Nathalie Bonnefoy、Pascale Moreau

  DOI：10.1016/j.ejmech.2012.09.012

  日期：2012.11

  The synthesis of quinoline derivatives, designed to interact with BCl-x(L), and to inhibit its interaction with pro-apoptotic partners, is described and their biological effects investigated. We showed that 5 out of 28 synthetized compounds restored cell death of 3T3 cells overexpressing Bcl-x(L) following serum starvation. Active compounds were further characterized for their binding capacity to the anti-apoptotic member of the Bcl-2 family, Bcl-x(L) as well as Bcl-2, Bcl-x(L) and Mcl-1, and for their pro-apoptotic activities toward lymphoid tumor cells and peripheral blood mononuclear cells. Altogether our results indicate that dimeric, rather than trimeric quinoline derivatives, represent a new attractive class of BH3 mimetics for cancer therapy. (C) 2012 Elsevier Masson SAS. All rights reserved.