(E)-2-(5,6-dichloro-1H-benzo[d][1,2,3]triazol-1-yl)-3-p-tolylacrylonitrile | 1335203-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: (E)-2-(5,6-dichloro-1H-benzo[d][1,2,3]triazol-1-yl)-3-p-tolylacrylonitrile
• 英文别名: (E)-2-(5,6-dichlorobenzotriazol-1-yl)-3-(4-methylphenyl)prop-2-enenitrile
• CAS: 1335203-59-2
• 化学式: C₁₆H₁₀Cl₂N₄
• 分子量: 329.188
• InChiKey: JOPYVSXRLPNJJW-WUXMJOGZSA-N

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：
  0.06
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,6-二氯苯并三唑 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.0h， 生成 (E)-2-(5,6-dichloro-1H-benzo[d][1,2,3]triazol-1-yl)-3-p-tolylacrylonitrile
  参考文献：
  名称：

  3-Aryl-2-[1H-benzotriazol-1-yl]acrylonitriles: A novel class of potent tubulin inhibitors

  摘要：

  During a screening for compounds that could act against Mycobacterium tuberculosis, a series of new cellular antiproliferative agents was identified. The most cytotoxic molecules were evaluated against a panel of human cell lines derived from hematological and solid human tumors. In particular, (E)-2-(1H-benzo[d] [1,2,3]triazol-1-yl)-3-(4-methoxyphenyl)acrylonitrile (1) was found to be of a potency comparable to etoposide and greater than 6-mercaptopurine in all cell lines tested. Accordingly, a synthesis of a new series of (E)-2-(5,6-dichloro-1H-benzo[d] [1,2,3]triazol-1-yl)-3-(4-R-phenyl)acrylonitriles was conducted in order to extend the studies of structure-activity relationship (SAR) for this class of molecules. With the aim to evaluate if 3-aryl-2-[1H-benzotriazol-1-yl]acrylonitriles were able to act like tubulin binding agents, the effects on cell cycle distribution of the most active compounds (1, 2a, 3 and 4) were analyzed in K562 cells. A detailed molecular modeling study of the putative binding mode of this series of compounds on tubulin is also reported. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.018

文献信息

• 3-Aryl-2-[1H-benzotriazol-1-yl]acrylonitriles: A novel class of potent tubulin inhibitors
  作者：Antonio Carta、Irene Briguglio、Sandra Piras、Giampiero Boatto、Paolo La Colla、Roberta Loddo、Manlio Tolomeo、Stefania Grimaudo、Antonietta Di Cristina、Rosaria Maria Pipitone、Erik Laurini、Maria Silvia Paneni、Paola Posocco、Maurizio Fermeglia、Sabrina Pricl

  DOI：10.1016/j.ejmech.2011.06.018

  日期：2011.9

  During a screening for compounds that could act against Mycobacterium tuberculosis, a series of new cellular antiproliferative agents was identified. The most cytotoxic molecules were evaluated against a panel of human cell lines derived from hematological and solid human tumors. In particular, (E)-2-(1H-benzo[d] [1,2,3]triazol-1-yl)-3-(4-methoxyphenyl)acrylonitrile (1) was found to be of a potency comparable to etoposide and greater than 6-mercaptopurine in all cell lines tested. Accordingly, a synthesis of a new series of (E)-2-(5,6-dichloro-1H-benzo[d] [1,2,3]triazol-1-yl)-3-(4-R-phenyl)acrylonitriles was conducted in order to extend the studies of structure-activity relationship (SAR) for this class of molecules. With the aim to evaluate if 3-aryl-2-[1H-benzotriazol-1-yl]acrylonitriles were able to act like tubulin binding agents, the effects on cell cycle distribution of the most active compounds (1, 2a, 3 and 4) were analyzed in K562 cells. A detailed molecular modeling study of the putative binding mode of this series of compounds on tubulin is also reported. (C) 2011 Elsevier Masson SAS. All rights reserved.