(E)-3-(3,5-dinitrophenyl)acryloyl chloride | 146324-14-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,5-dinitrophenyl)acryloyl chloride
• 英文别名: (E)-3-(3,5-Dinitro-phenyl)-acryloyl chloride
• CAS: 146324-14-3
• 化学式: C₉H₅ClN₂O₅
• 分子量: 256.602
• InChiKey: XUFRFVDXFMQPIW-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103.35
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,5-dinitrophenyl)acryloyl chloride 在 氯化亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (E)-2-(3,5-dinitrostyryl)-4,4-dimethyl-2-oxazoline hydrochloride
  参考文献：
  名称：

  Mehta; Musso; White, European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 443 - 446

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-dinitrocinnamic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(3,5-dinitrophenyl)acryloyl chloride
  参考文献：
  名称：

  Synthesis and in vitro and in vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids

  摘要：

  Fourteen bergenin/cinnamic acid hybrids were synthesized, characterized and evaluated for their anti-tumour activity both in vitro and in vivo. The most potent compound, 5c, arrested HepG2 cells (IC50 = 4.23 +/- 0.79 mu M) in the G2/M phase and induced cellular apoptosis. Moreover, compound 5c was also found to suppress the tumour growth in Heps xenograft-bearing mice with low toxicity. In the mechanistic study, 5c administration ignited a mitochondria-mediated apoptosis pathway of HepG2 cell death. Furthermore, 5c activated Akt-dependent pathways and further decreased the expression of the Bc1-2 family of proteins. The downstream mitochondrial p53 translocation was also significantly activated, accompanied by an increase of the caspase-9, caspase-3 activation. These data imply that bergenin/cinnamic acid hybrids could serve as novel Akt/Bcl-2 inhibitors for further preclinical studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.053