4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-7-methoxy-3-phenyl-2H-chromen-2-one | 740810-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-7-methoxy-3-phenyl-2H-chromen-2-one
• 英文别名: 7-Methoxy-3-phenyl-4-[4-(2-piperidin-1-ylethoxy)phenyl]chromen-2-one；7-methoxy-3-phenyl-4-[4-(2-piperidin-1-ylethoxy)phenyl]chromen-2-one
• CAS: 740810-08-6
• 化学式: C₂₉H₂₉NO₄
• 分子量: 455.554
• InChiKey: NAULGZBXUQZGCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-7-methoxy-3-phenyl-2H-chromen-2-one 在 aluminum tri-bromide 、 乙二醇 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到7-Hydroxy-3-phenyl-4-[4-(2-piperidin-1-ylethoxy)phenyl]chromen-2-one
  参考文献：
  名称：

  Lead identification of a potent benzopyranone selective estrogen receptor modulator

  摘要：

  Starting from a phenol screening hit (6), three series of benzopyranone selective estrogen receptor modulators (SERMs) have been designed, synthesized, and analyzed for both estrogen receptor alpha binding affinity and in vitro activity in two cell assays. The lead compound identified, SP500263 (13), was more potent than raloxifene and tamoxifen in a cell-based assay measuring inhibition of interleukin-6 release. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.081
• 作为产物：
  描述：

  4-(4-羟基苯基)-7-甲氧基-3-苯基色烯-2-酮 在 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.0h， 生成 4-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-7-methoxy-3-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activities of novel triphenylethylene–coumarin hybrids, and their interactions with Ct-DNA

  摘要：

  Novel triphenylethylene-coumarin hybrid derivatives containing different amounts of amino side chains Were designed and synthesized in good yields under microwave radiation. The derivatives 5b-d which possessed two amino side chains (except morpholinyl) showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 10c, 5c, and 13c bearing amino side chain (except morpholinyl) on 4-phenyl had significant interactions with Ct-DNA by the intercalative mode of binding. Structure-activity relationships (SARs) analysis suggested that the amino alkyl chain would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.009