(2E,5E)-2,5-bis(2-fluorobenzylidene)cyclopentanone | 1158188-88-5

• 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: (2E,5E)-2,5-bis(2-fluorobenzylidene)cyclopentanone
• 英文别名: 2,5-bis((E)-2-fluorobenzylidene)cyclopentan-1-one；(2E,5E)-2,5-bis[(2-fluorophenyl)methylidene]cyclopentan-1-one
• CAS: 1158188-88-5
• 化学式: C₁₉H₁₄F₂O
• 分子量: 296.316
• InChiKey: FGVSGXYJPMHZQB-JOBJLJCHSA-N

物化性质

• 熔点：
  207-209 °C
• 沸点：
  460.0±45.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 (2E,5E)-2,5-bis(2-fluorobenzylidene)cyclopentanone 、 苊醌 以 甲醇 为溶剂， 反应 0.5h， 以92.6%的产率得到1-methyl-4-(2-fluorophenyl)pyrrolo(spiro[2.2'']acenaphthene-1''-one)-spiro[3.2']-5'-[(2-fluorophenyl)methylidene]cyclopentanone
  参考文献：
  名称：

  A Highly Atom Economic, Chemo-, Regio- and Stereoselective Synthesis and Crystal Structure of Novel Spiro-Cyclopentanone

  摘要：

  从苊醌和 a-氨基酸（肌氨酸）衍生出的偶氮甲基酰化物与一系列 2,5-双（氟亚苄基）环戊酮进行 1,3-二极环加成反应，以化学、区域和立体选择性的方式得到了新颖的螺环戊酮-吡咯烷类化合物，定量收率为 95-96%。文中描述了一种含有双（2,6- 二氟苄）（2b）的化合物的晶体结构。双（2,6-二氟苄）(2b) 中的环戊烷环具有包络构象。

  DOI：

  10.14233/ajchem.2013.15413
• 作为产物：
  描述：

  2-氟苯甲醛 、 环戊酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 (2E,5E)-2,5-bis(2-fluorobenzylidene)cyclopentanone
  参考文献：
  名称：

  Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors

  摘要：

  对47种合成的姜黄素样二芳基戊烷类类似物进行了抗黑色素生成筛选，结果显示其中一些对B16黑色素瘤细胞的黑色素生成具有强抑制作用。这些作用主要被认为是通过抑制酪氨酸酶活性、抑制酪氨酸酶表达和降解黑色素色素实现的。还讨论了那些抑制黑色素生成和酪氨酸酶活性的姜黄素样二芳基戊烷类类似物的结构-活性关系。在测试的化合物中，（2E,6E）-2,6-双（2,5-二甲氧基苄叉）环己酮显示了最强的抗黑色素生成效果，其机制被认为是在B16黑色素瘤细胞中降解黑色素色素，既不影响酪氨酸酶活性也不影响酪氨酸酶表达。

  DOI：

  10.1007/s11418-011-0568-0

文献信息

• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.
• Synthesis and anti-tumor activity of EF24 analogues as IKKβ inhibitors
  作者：Rong Jin、Qiuxiang Chen、Song Yao、Encheng Bai、Weitao Fu、Ledan Wang、Jiabing Wang、Xiaojing Du、Tao Wei、Haineng Xu、Chengxi Jiang、Peihong Qiu、Jianzhang Wu、Wulan Li、Guang Liang

  DOI：10.1016/j.ejmech.2017.11.077

  日期：2018.1

  EF24 is an IKK beta inhibitor (IC50: 72 mu M) containing various anti-tumor activities. In this study, a series of EF24 analogs targeting IKK beta were designed and synthesized. Several IKK beta inhibitors with better activities than EF24 were screened out and B3 showed best IKK beta inhibitory (IC50: 6.6 mu M). Molecular docking and dynamic simulation experiments further confirmed this inhibitory effect. B3 obviously suppressed the viability of Hela229, A549, SGC-7901 and MGC-803 cells. Then, in SGC-7901 and MGC-803 cells, B3 blocked the NF-kappa B signal pathway by inhibiting IKK beta phosphorylation, and followed arrested the cell cycle at G2/M phase by suppressing the Cyclin B1 and Cdc2 p34 expression, induced the cell apoptosis by down-regulating Bcl-2 protein and up-regulating cleaved-caspase3. Moreover, B3 significantly reduced tumor growth and suppressed the IKK beta-NF-kappa B signal pathway in SGC-7901 xenograft model. In total, this study present a potential IKK beta inhibitor as anti-tumor precursor. (C) 2017 Published by Elsevier Masson SAS.