ethyl (Z)-3-(3-bromo-4-methoxyphenyl)-2-cyanoprop-2-enoate

• 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: ethyl (Z)-3-(3-bromo-4-methoxyphenyl)-2-cyanoprop-2-enoate
• 化学式: C₁₃H₁₂BrNO₃
• 分子量: 310.147
• InChiKey: ZFAWVVVJOUYWDB-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-nitrobenzyl)-thiazolidine-2,4-dione 、 ethyl (Z)-3-(3-bromo-4-methoxyphenyl)-2-cyanoprop-2-enoate 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (5Z)-5-(3-bromo-4-methoxybenzylidene)-3-(4-nitrobenzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis, in vitro anticancer activity and in silico study of new disubstituted thiazolidinedione derivatives

  摘要：

  Thiazolidinediones are known to have antidiabetic activity, but new activities are being discovered every year; among these, their anticancer activity has received the most attention. In this study, we synthesized three new disubstituted thiazolidinediones and assayed their cytotoxicity against six tumor cell lines, as well as against normal cells. Cytometry studies and molecular modeling were also performed to elucidate the mechanism of cytotoxicity. Of the three new thiazolidinediones synthesized, (5Z)-5-(3-bromo-benzylidene)-3-(4-nitrobenzyl)-thiazolidine-2,4-dione (LPSF/SF-13) exhibited the most promising activity; it was selectively cytotoxic against leukemia, lymphoma, glioblastoma, and hepatocarcinoma cell lines without being toxic to normal cells. Apoptosis was the main cell death process induced by this compound, although it also induced necrosis. Furthermore, molecular modeling studies showed that LPSF/SF-13 had good affinity for peroxisome proliferator-activated receptor gamma; binding to the receptor involved hydrogen bonds with Arg288 and Ser342 residues (bond distances of 3.1 and 2.8 , respectively), as well as a pi-bonding interaction with His449. We concluded that LPSF/SF-13 is a promising compound for in vivo and combination therapy studies against cancer.

  DOI：

  10.1007/s00044-013-0902-z
• 作为产物：
  描述：

  3-溴-4-甲氧基苯甲醛 、 氰乙酸乙酯 生成 ethyl (Z)-3-(3-bromo-4-methoxyphenyl)-2-cyanoprop-2-enoate
  参考文献：
  名称：

  Synthesis, in vitro anticancer activity and in silico study of new disubstituted thiazolidinedione derivatives

  摘要：

  Thiazolidinediones are known to have antidiabetic activity, but new activities are being discovered every year; among these, their anticancer activity has received the most attention. In this study, we synthesized three new disubstituted thiazolidinediones and assayed their cytotoxicity against six tumor cell lines, as well as against normal cells. Cytometry studies and molecular modeling were also performed to elucidate the mechanism of cytotoxicity. Of the three new thiazolidinediones synthesized, (5Z)-5-(3-bromo-benzylidene)-3-(4-nitrobenzyl)-thiazolidine-2,4-dione (LPSF/SF-13) exhibited the most promising activity; it was selectively cytotoxic against leukemia, lymphoma, glioblastoma, and hepatocarcinoma cell lines without being toxic to normal cells. Apoptosis was the main cell death process induced by this compound, although it also induced necrosis. Furthermore, molecular modeling studies showed that LPSF/SF-13 had good affinity for peroxisome proliferator-activated receptor gamma; binding to the receptor involved hydrogen bonds with Arg288 and Ser342 residues (bond distances of 3.1 and 2.8 , respectively), as well as a pi-bonding interaction with His449. We concluded that LPSF/SF-13 is a promising compound for in vivo and combination therapy studies against cancer.

  DOI：

  10.1007/s00044-013-0902-z