(3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(3-(3,4-dimethoxybenzoyl)benzylidene)piperazine-2,5-dione | 1314313-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(3-(3,4-dimethoxybenzoyl)benzylidene)piperazine-2,5-dione
• 英文别名: (3Z,6Z)-3-[(5-tert-butyl-1H-imidazol-4-yl)methylidene]-6-[[3-(3,4-dimethoxybenzoyl)phenyl]methylidene]piperazine-2,5-dione
• CAS: 1314313-90-0
• 化学式: C₂₈H₂₈N₄O₅
• 分子量: 500.554
• InChiKey: RFRFSHTZXQESPT-KGDRBKAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,3,4-三甲氧基-n-甲基苯甲酰胺 在 重铬酸吡啶 、 正丁基锂 、 二异丁基氢化铝 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 (3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(3-(3,4-dimethoxybenzoyl)benzylidene)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059

文献信息

• [EN] ANALOGS OF DEHYDROPHENYLAHISTINS<br/>[FR] ANALOGUES DE DÉSHYDROPHÉNYLAHISTINES
  申请人：NEREUS PHARMACEUTICALS INC

  公开号：WO2011084962A1

  公开（公告）日：2011-07-14

  Analogs of dehydrophenylahistins are disclosed as are methods for making such compounds. Compositions and methods for treating various disease conditions including cancer and non-cancer diseases associated with vascular proliferation are also disclosed.

  揭示了脱氢苯酚组合物的类似物，以及制备这类化合物的方法。还揭示了用于治疗包括癌症和与血管增殖有关的非癌症疾病等各种疾病状况的组合物和方法。