ethyl (Z)-3-(3-bromophenyl)-2-cyanoprop-2-enoate | 947739-62-0

• 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-bromophenyl)-2-cyanoprop-2-enoate
• CAS: 947739-62-0
• 化学式: C₁₂H₁₀BrNO₂
• 分子量: 280.121
• InChiKey: OTVZAMWNYOAFBV-POHAHGRESA-N

物化性质

• 沸点：
  384.2±37.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-3-(3-bromophenyl)-2-cyanoprop-2-enoate 在 2,3-dihydro-2-(3-bromophenyl)-1H-benzoimidazole 作用下， 生成 3-(3-bromo-phenyl)-2-cyano-propionic acid ethyl ester
  参考文献：
  名称：

  Unprecedented Reaction between Ethyl α-Cyanocinnamate and o-Phenylenediamine: Development of an Efficient Method for the Transfer Hydrogenation of Electronically Depleted Olefins

  摘要：

  在热条件下，乙基α-氰基肉桂酸酯与邻苯二胺的反应生成了2-氰基-3-苯基丙酸乙酯、2-苯基苯并咪唑和乙基氰乙酸酯。机制上的揭示促成了一种简单高效的转移氢化过程，从原位生成的苯并咪唑啉到活化烯烃，在无溶剂和无催化剂的条件下进行。

  DOI：

  10.1055/s-2007-991087
• 作为产物：
  描述：

  间溴苯甲醛 、 氰乙酸乙酯 生成 ethyl (Z)-3-(3-bromophenyl)-2-cyanoprop-2-enoate
  参考文献：
  名称：

  Unprecedented Reaction between Ethyl α-Cyanocinnamate and o-Phenylenediamine: Development of an Efficient Method for the Transfer Hydrogenation of Electronically Depleted Olefins

  摘要：

  在热条件下，乙基α-氰基肉桂酸酯与邻苯二胺的反应生成了2-氰基-3-苯基丙酸乙酯、2-苯基苯并咪唑和乙基氰乙酸酯。机制上的揭示促成了一种简单高效的转移氢化过程，从原位生成的苯并咪唑啉到活化烯烃，在无溶剂和无催化剂的条件下进行。

  DOI：

  10.1055/s-2007-991087

文献信息

• Synthesis, in vitro anticancer activity and in silico study of new disubstituted thiazolidinedione derivatives
  作者：Moacyr Jesus Barreto de Melo Rêgo、Marina Rocha Galdino-Pitta、Daniel Tarciso Martins Pereira、Juliana Cruz da Silva、Marcelo Montenegro Rabello、Maria do Carmo Alves de Lima、Marcelo Zaldini Hernandes、Ivan da Rocha Pitta、Suely Lins Galdino、Maira Galdino da Rocha Pitta

  DOI：10.1007/s00044-013-0902-z

  日期：2014.6

  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.