1-[4-(5-bromopyrimidin-2-ylsulfanyl)-phenyl]-3-(2-nitrobenzoyl)urea | 886572-78-7

• 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: 1-[4-(5-bromopyrimidin-2-ylsulfanyl)-phenyl]-3-(2-nitrobenzoyl)urea
• 英文别名: 1-[4-(5-Bromopyrimidin-2-ylsulfanyl)phenyl]-3-(2-nitrobenzoyl)urea；N-[[4-(5-bromopyrimidin-2-yl)sulfanylphenyl]carbamoyl]-2-nitrobenzamide
• CAS: 886572-78-7
• 化学式: C₁₈H₁₂BrN₅O₄S
• 分子量: 474.294
• InChiKey: VGWNSNNCXCIKIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[4-(5-bromopyrimidin-2-ylsulfanyl)-phenyl]-3-(2-nitrobenzoyl)urea 在 铁粉 乙酸乙酯 、 silica gel 、 ethyl acetate n-hexane 作用下， 以 溶剂黄146 、 水 为溶剂， 反应 0.5h， 以to give 7d, yield 62%的产率得到1-(2-aminobenzoyl)-3-[4-(5-bromopyrimidin-2-ylsulfanyl)phenyl]urea
  参考文献：
  名称：

  Synthesis of novel tubulin polymerization inhibitors: benzoylphenylurea (BPU) sulfur analogs

  摘要：

  一系列的BPU类似物被合成并用于抗肿瘤活性评估。特别是BPU硫类似物6n和7d显示出与化合物1相比，对癌细胞系具有高达10倍的增强效力。6n比化合物1更有效地导致MCF-7细胞凋亡。与具有类似作用机制的其他药物相比，6n保持了显著的抑制微管组装的能力，其IC50为2.1μM。

  公开号：

  US07595326B2
• 作为产物：
  描述：

  4-氨基苯硫酚 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 20.5h， 生成 1-[4-(5-bromopyrimidin-2-ylsulfanyl)-phenyl]-3-(2-nitrobenzoyl)urea
  参考文献：
  名称：

  Benzoylphenylurea Sulfur Analogues with Potent Antitumor Activity

  摘要：

  A novel series of BPU analogues were synthesized and evaluated for antitumor activity. In particular, BPU sulfur analogues 6n and 7d were shown to possess up to10-fold increased potency, when compared to I (NSC-639829), against cancer cell lines. 6n was more effective than I in causing apoptosis of MCF-7 cells. When compared to other drugs with a similar mechanism of action, 6n retained significant ability to inhibit tubulin assembly, with an IC50 of 2.1 mu M.

  DOI：

  10.1021/jm051261s

文献信息

• SYNTHESIS OF NOVEL TUBULIN POLYMERIZATION INHIBITORS: BENZOYLPHENYLUREA (BPU) SULFUR ANALOGS
  申请人：Khan Saeed R.

  公开号：US20090099218A1

  公开（公告）日：2009-04-16

  This invention provides a series of BPU analogues; their synthesis and evaluated biological activity. BPU sulfur analogues were found to possess up to 20 fold increased potency, when compared to compound 1, in various cancerous cell lines.

  这项发明提供了一系列BPU类似物；它们的合成和评估生物活性。与化合物1相比，BPU硫类似物在各种癌细胞系中被发现具有高达20倍的增强效力。
• DESIGN AND SYNTHESIS OF NOVEL TUBULIN POLYMERIZATION INHIBITORS: BENZOYLPHENYLUREA (BPU) SULFUR ANALOGS
  申请人：Khan R. Saeed

  公开号：US20070232631A1

  公开（公告）日：2007-10-04

  A novel series of BPU analogues were synthesized and evaluated for antitumor activity. In particular, BPU sulfur analogues 6 n and 7 d were shown to possess up to 10-fold increased potency, when compared to compound 1, against cancer cell lines. 6 n was more effective than compound 1 in causing apoptosis of MCF-7 cells. When compared to other drugs with a similar mechanism of action, 6 n retained significant ability to inhibit tubulin assembly, with an IC 50 of 2.1 μM.

  一系列的BPU类似物被合成并评估其抗肿瘤活性。特别是，BPU硫类似物6n和7d相对于化合物1，在癌细胞系中表现出高达10倍的增强效力。6n比化合物1更有效地引起MCF-7细胞的凋亡。与其他具有类似作用机制的药物相比，6n保留了显著的抑制微管组装的能力，IC50为2.1μM。
• Design and synthesis of novel tubulin polymerization inhibitors: benzoylphenylurea (BPU) sulfur analogs
  申请人：Champions Biotechnology, Inc.

  公开号：EP2055697A1

  公开（公告）日：2009-05-06

  This invention provides a series of BPU analogues such as those of formula (XXX); their synthesis and evaluated biological activity. BPU sulfur analogues were found to possess up to 20 fold increased potency, when compared to reference compound 1, in various cancerous cell lines.

  本发明提供了一系列 BPU 类似物，如式 (XXX)；它们的合成和生物活性评估。研究发现，与参考化合物 1 相比，BPU 硫类似物在各种癌细胞系中的效力最多可提高 20 倍。
• WO2006/113650
  申请人：——

  公开号：——

  公开（公告）日：——
• DESIGN AND SYNTHESIS OF NOVEL TUBULIN POLYMERIZATION INHIBITORS: BONZOYLPHENYLURIA (BPU) SULFUR ANALOGS
  申请人：Khan, Saeed R.

  公开号：EP1907367A1

  公开（公告）日：2008-04-09