(((3S)-1,7-bis(4-(benzyloxy)phenyl)-7-(2,4,6-trimethoxyphenyl)hept-5-yn-3-yl)oxy)triethylsilane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (((3S)-1,7-bis(4-(benzyloxy)phenyl)-7-(2,4,6-trimethoxyphenyl)hept-5-yn-3-yl)oxy)triethylsilane
• 英文别名: [(3S)-1,7-bis(4-phenylmethoxyphenyl)-7-(2,4,6-trimethoxyphenyl)hept-5-yn-3-yl]oxy-triethylsilane
• 化学式: C₄₈H₅₆O₆Si
• 分子量: 757.055
• InChiKey: BAHFQMCBTZGFSJ-LOARSGCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.42
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (((3S)-1,7-bis(4-(benzyloxy)phenyl)-7-(2,4,6-trimethoxyphenyl)hept-5-yn-3-yl)oxy)triethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到(3S)-1,7-bis(4-(benzyloxy)phenyl)-7-(2,4,6-trimethoxyphenyl)hept-5-yn-3-ol
  参考文献：
  名称：

  Design, synthesis, and evaluation of curcumin-derived arylheptanoids for glioblastoma and neuroblastoma cytotoxicity

  摘要：

  Using an innovative approach toward multiple carbon-carbon bond-formations that relies on the multifaceted catalytic properties of titanocene complexes we constructed a series of C1-C7 analogs of curcumin for evaluation as brain and peripheral nervous system anti-cancer agents. C2-Arylated analogs proved efficacious against neuroblastoma (SK-N-SH & SK-N-FI) and glioblastoma multiforme (U87MG) cell lines. Similar inhibitory activity was also evident in p53 knockdown U87MG GBM cells. Furthermore, lead compounds showed limited growth inhibition in vitro against normal primary human CD34+ hematopoietic progenitor cells. Taken together, the present findings indicate that these curcumin analogs are viable lead compounds for the development of new central and peripheral nervous system cancer chemotherapeutics with the potential for little effects on normal hematopoietic progenitor cells. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.095
• 作为产物：
  描述：

  (S)-1-(4-benzyloxyphenyl)hex-5-yn-3-ol 在 咪唑 、 二氯二茂钛 、 正丁基锂 、 三叔丁基膦 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.67h， 生成 (((3S)-1,7-bis(4-(benzyloxy)phenyl)-7-(2,4,6-trimethoxyphenyl)hept-5-yn-3-yl)oxy)triethylsilane
  参考文献：
  名称：

  Titanocene-Catalyzed Multicomponent Coupling Approach to Diarylethynyl Methanes

  摘要：

  A titanocene-catalyzed multicomponent coupling to provide diarylethynyl methanes is described. By combining the multifunctionality of Cp2TiCl2 with the traceless dielectrophilicity of aryl aldehydes, all-carbon tertiary centers are obtained in 55-99% yield.

  DOI：

  10.1021/ja308891e

文献信息

• Titanocene-Catalyzed Multicomponent Coupling Approach to Diarylethynyl Methanes
  作者：Joseph B. Gianino、Brandon L. Ashfeld

  DOI：10.1021/ja308891e

  日期：2012.11.7

  A titanocene-catalyzed multicomponent coupling to provide diarylethynyl methanes is described. By combining the multifunctionality of Cp2TiCl2 with the traceless dielectrophilicity of aryl aldehydes, all-carbon tertiary centers are obtained in 55-99% yield.
• Design, synthesis, and evaluation of curcumin-derived arylheptanoids for glioblastoma and neuroblastoma cytotoxicity
  作者：Catherine A. Campos、Joseph B. Gianino、Barbara J. Bailey、Mary E. Baluyut、Constanze Wiek、Helmut Hanenberg、Harlan E. Shannon、Karen E. Pollok、Brandon L. Ashfeld

  DOI：10.1016/j.bmcl.2013.09.095

  日期：2013.12

  Using an innovative approach toward multiple carbon-carbon bond-formations that relies on the multifaceted catalytic properties of titanocene complexes we constructed a series of C1-C7 analogs of curcumin for evaluation as brain and peripheral nervous system anti-cancer agents. C2-Arylated analogs proved efficacious against neuroblastoma (SK-N-SH & SK-N-FI) and glioblastoma multiforme (U87MG) cell lines. Similar inhibitory activity was also evident in p53 knockdown U87MG GBM cells. Furthermore, lead compounds showed limited growth inhibition in vitro against normal primary human CD34+ hematopoietic progenitor cells. Taken together, the present findings indicate that these curcumin analogs are viable lead compounds for the development of new central and peripheral nervous system cancer chemotherapeutics with the potential for little effects on normal hematopoietic progenitor cells. (C) 2013 Elsevier Ltd. All rights reserved.