(2E)-1-{4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one | 1350753-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-{4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(2,4,5-trimethoxyphenyl)-1-[4-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]phenyl]prop-2-en-1-one；(E)-3-(2,4,5-trimethoxyphenyl)-1-[4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]prop-2-en-1-one
• CAS: 1350753-36-4
• 化学式: C₂₉H₃₀O₇
• 分子量: 490.553
• InChiKey: QFKMWXBKCXQYNT-SCCLZRITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(4-Iodophenyl)-3-(2,4,5-trimethoxyphenyl)-2-propen-1-one 在 哌啶 、 四(三苯基膦)钯 、 potassium carbonate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 38.0h， 生成 (2E)-1-{4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Stilbene–Chalcone Hybrids: Design, Synthesis, and Evaluation as a New Class of Antimalarial Scaffolds That Trigger Cell Death through Stage Specific Apoptosis

  摘要：

  Novel stilbene-chalcone (S-C) hybrids were synthesized via a sequential Claisen-Schmidt-Knoevenagel-Heck approach and evaluated for antiplasmodial activity in in vitro red cell culture using SYBR Green I assay. The most potent hybrid (11) showed IC50 of 2.2, 1.4, and 6.4 mu M against 3D7 (chloroquine sensitive), Indo, and Dd2 (chloroquine resistant) strains of Plasmodium falciparum, respectively. Interestingly, the respective individual stilbene (IC50 > 100 mu M), chalcone (IC50 = 11.5 mu M), or an equimolar mixture of stilbene and chalcone (IC50 = 32.5 mu M) were less potent than 11. Studies done using specific stage enriched cultures and parasite in continuous culture indicate that 11 and 18 spare the schizont but block the progression of the parasite life cycle at the ring or the trophozoite stages. Further, 11 and 18 caused chromatin condensation, DNA fragmentation, and loss of mitochondrial membrane potential in Plasmodium falciparum, thereby suggesting their ability to cause apoptosis in malaria parasite.

  DOI：

  10.1021/jm201216y

文献信息

• Stilbene–Chalcone Hybrids: Design, Synthesis, and Evaluation as a New Class of Antimalarial Scaffolds That Trigger Cell Death through Stage Specific Apoptosis
  作者：Naina Sharma、Dinesh Mohanakrishnan、Amit Shard、Abhishek Sharma、Saima、Arun K. Sinha、Dinkar Sahal

  DOI：10.1021/jm201216y

  日期：2012.1.12

  Novel stilbene-chalcone (S-C) hybrids were synthesized via a sequential Claisen-Schmidt-Knoevenagel-Heck approach and evaluated for antiplasmodial activity in in vitro red cell culture using SYBR Green I assay. The most potent hybrid (11) showed IC50 of 2.2, 1.4, and 6.4 mu M against 3D7 (chloroquine sensitive), Indo, and Dd2 (chloroquine resistant) strains of Plasmodium falciparum, respectively. Interestingly, the respective individual stilbene (IC50 > 100 mu M), chalcone (IC50 = 11.5 mu M), or an equimolar mixture of stilbene and chalcone (IC50 = 32.5 mu M) were less potent than 11. Studies done using specific stage enriched cultures and parasite in continuous culture indicate that 11 and 18 spare the schizont but block the progression of the parasite life cycle at the ring or the trophozoite stages. Further, 11 and 18 caused chromatin condensation, DNA fragmentation, and loss of mitochondrial membrane potential in Plasmodium falciparum, thereby suggesting their ability to cause apoptosis in malaria parasite.