7-bromo-5-(propen-2-yl)-2-(pyrrolidin-1-yl)quinoline | 1415663-37-4

• 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: 7-bromo-5-(propen-2-yl)-2-(pyrrolidin-1-yl)quinoline
• 英文别名: 7-Bromo-5-prop-1-en-2-yl-2-pyrrolidin-1-ylquinoline；7-bromo-5-prop-1-en-2-yl-2-pyrrolidin-1-ylquinoline
• CAS: 1415663-37-4
• 化学式: C₁₆H₁₇BrN₂
• 分子量: 317.228
• InChiKey: AGCULISVPGIMOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-bromo-5-(propen-2-yl)-2-(pyrrolidin-1-yl)quinoline 在 platinum(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 2.33h， 生成 4-[3-[2-Ethoxy-5-propan-2-yl-3-(5-propan-2-yl-2-pyrrolidin-1-ylquinolin-7-yl)quinolin-7-yl]quinolin-2-yl]morpholine
  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：

  四氢吡咯 、 7-bromo-2-chloro-5-(propen-2-yl)quinoline 反应 2.0h， 以94%的产率得到7-bromo-5-(propen-2-yl)-2-(pyrrolidin-1-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

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.