3-(4-chlorobenzoyl)benzaldehyde | 1267436-21-4

• 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: 3-(4-chlorobenzoyl)benzaldehyde
• 英文别名: 3-(4-Chlorobenzoyl)benzaldehyde
• CAS: 1267436-21-4
• 化学式: C₁₄H₉ClO₂
• 分子量: 244.677
• InChiKey: LTZALUABMMAXGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-acetyl-3-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)piperazine-2,5-dione 、 3-(4-chlorobenzoyl)benzaldehyde 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以13%的产率得到(3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(3-(4-chlorobenzoyl)benzylidene)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059
• 作为产物：
  描述：

  3-(4-chlorobenzoyl)benzonitrile 在 重铬酸吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 3-(4-chlorobenzoyl)benzaldehyde
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059

文献信息

• 一种常压下铜催化合成二芳甲酮的方法
  申请人：南京师范大学

  公开号：CN103951537B

  公开（公告）日：2017-04-05

  本发明公开了一种常压下铜催化合成二芳甲酮类化合物的方法，在溶剂醇或醇的水溶液中，在碱和酸的作用下，加入铜催化剂，常压下芳基碘代物、芳基硼酸与一氧化碳直接交叉偶联反应制备二芳甲酮类化合物。本发明的羰基化Suzuki偶联反应制备二芳甲酮类化合物的方法，具有催化剂来源广泛、廉价和毒性小；反应无需配体且活性好；反应常压进行且选择性高；底物来源广泛且稳定；官能团相容性好且底物的适用范围广；反应介质绿色且可以循环回收等优点。在优化的反应条件之下，目标产品分离收率高达95%。
• Copper-catalyzed carbonylative Suzuki coupling of aryl iodides with arylboronic acids under ambient pressure of carbon monoxide
  作者：Laijin Cheng、Yanzhen Zhong、Zhuchao Ni、Hongyan Du、Fengli Jin、Qi Rong、Wei Han

  DOI：10.1039/c4ra08594a

  日期：——

  An efficient and ligandless nanocopper-catalyzed carbonylative cross-coupling of aryl iodides with arylboronic acids at ambient CO pressure in poly(ethylene glycol), has been developed.

  在聚乙二醇中，一种高效且无需配体的纳米铜催化的羰基化交叉偶联反应被开发出来，可以在常压一氧化碳下实现芳香碘化物与芳香硼酸的转化。

• Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents
  作者：Yuri Yamazaki、Makiko Sumikura、Yurika Masuda、Yoshiki Hayashi、Hiroyuki Yasui、Yoshiaki Kiso、Takumi Chinen、Takeo Usui、Fumika Yakushiji、Barbara Potts、Saskia Neuteboom、Michael Palladino、George Kenneth Lloyd、Yoshio Hayashi

  DOI：10.1016/j.bmc.2012.05.059

  日期：2012.7

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.