2-(2-dimethylamino-ethyl)-7-(2-isothiocyanato-ethyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone | 1357912-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2-dimethylamino-ethyl)-7-(2-isothiocyanato-ethyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone
• 英文别名: 6-[2-(Dimethylamino)ethyl]-13-(2-isothiocyanatoethyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 1357912-84-5
• 化学式: C₂₁H₁₈N₄O₄S
• 分子量: 422.464
• InChiKey: DFLLESXVHVLXDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(2-dimethylamino-ethyl)-7-(2-isothiocyanato-ethyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new naphtalene diimides bearing isothiocyanate functionality

  摘要：

  The synthesis and the biological activities of new derivatives 1-3, characterized by the isothiocyanate (ITC) functionalities coming from sulforaphane (SFN), a well-known anticancer natural product, were reported. The most interesting compound of the series was 2. It was chemically characterized by two ITC functionalities mounted on the 1,4,5,8-naphthalentetracarboxylic diimide (NDI) scaffold through two polymethylene chains, each constituted by three carbon units. It demonstrated an IC50 value in the submicromolar range, more potent than SFN, displaying also the ability to trigger apoptotic induction in the same range by eliciting both extrinsic and intrinsic apoptotic pathways. Finally, it was observed that 2 inhibited the cell growth by blocking the cell cycle in G1 phase. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.003

文献信息

• Design, synthesis and biological evaluation of new naphtalene diimides bearing isothiocyanate functionality
  作者：Anna Minarini、Andrea Milelli、Vincenzo Tumiatti、Lorenzo Ferruzzi、Melinda-Rita Marton、Eleonora Turrini、Patrizia Hrelia、Carmela Fimognari

  DOI：10.1016/j.ejmech.2011.12.003

  日期：2012.2

  The synthesis and the biological activities of new derivatives 1-3, characterized by the isothiocyanate (ITC) functionalities coming from sulforaphane (SFN), a well-known anticancer natural product, were reported. The most interesting compound of the series was 2. It was chemically characterized by two ITC functionalities mounted on the 1,4,5,8-naphthalentetracarboxylic diimide (NDI) scaffold through two polymethylene chains, each constituted by three carbon units. It demonstrated an IC50 value in the submicromolar range, more potent than SFN, displaying also the ability to trigger apoptotic induction in the same range by eliciting both extrinsic and intrinsic apoptotic pathways. Finally, it was observed that 2 inhibited the cell growth by blocking the cell cycle in G1 phase. (C) 2011 Elsevier Masson SAS. All rights reserved.