benzyl 4-(2-(5-(3-(3,4-dichlorophenyl)ureido)-2-methylphenoxy)ethyl)piperazine-1-carboxylate | 1257423-71-4

• 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: benzyl 4-(2-(5-(3-(3,4-dichlorophenyl)ureido)-2-methylphenoxy)ethyl)piperazine-1-carboxylate
• CAS: 1257423-71-4
• 化学式: C₂₈H₃₀Cl₂N₄O₄
• 分子量: 557.477
• InChiKey: SKLLDPXTQRWSEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.14
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl 4-(2-(5-(3-(3,4-dichlorophenyl)ureido)-2-methylphenoxy)ethyl)piperazine-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 4-[2-(5-{[(3,4-dichlorophenyl)carbamoyl]amino}-2-methylphenoxy)ethyl]piperazine
  参考文献：
  名称：

  In vitro inhibition of translation initiation by N,N′-diarylureas—potential anti-cancer agents

  摘要：

  Symmetrical N,N'-diarylureas: 1,3-bis(3,4-dichlorophenyl)-, 1,3-bis[4-chloro-3-(trifluoromethyl)phenyl]- and 1,3-bis[3,5-bis(trifluoromethyl)phenyl]urea, were identified as potent activators of the eIF2 alpha kinase heme regulated inhibitor. They reduce the abundance of the eIF2.GTP.tRNA(i)(Met) ternary complex and inhibit cancer cell proliferation. An optimization process was undertaken to improve their solubility while preserving their biological activity. Non-symmetrical hybrid ureas were generated by combining one of the hydrophobic phenyl moieties present in the symmetrical ureas with the polar 3-hydroxy-tolyl moiety. O-alkylation of the later added potentially solubilizing charge bearing groups. The new non-symmetrical N,N'-diarylureas were characterized by ternary complex reporter gene and cell proliferation assays, demonstrating good bioactivities. A representative sample of these compounds potently induced phosphorylation of eIF2 alpha and expression of CHOP at the protein and mRNA levels. These inhibitors of translation initiation may become leads for the development of potent, non-toxic, and target specific anti-cancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.126
• 作为产物：
  描述：

  benzyl 4-[2-(2-methyl-5-nitrophenoxy)ethyl]piperazine-1-carboxylate 在 tin(II) chloride dihdyrate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 1.5h， 生成 benzyl 4-(2-(5-(3-(3,4-dichlorophenyl)ureido)-2-methylphenoxy)ethyl)piperazine-1-carboxylate
  参考文献：
  名称：

  In vitro inhibition of translation initiation by N,N′-diarylureas—potential anti-cancer agents

  摘要：

  Symmetrical N,N'-diarylureas: 1,3-bis(3,4-dichlorophenyl)-, 1,3-bis[4-chloro-3-(trifluoromethyl)phenyl]- and 1,3-bis[3,5-bis(trifluoromethyl)phenyl]urea, were identified as potent activators of the eIF2 alpha kinase heme regulated inhibitor. They reduce the abundance of the eIF2.GTP.tRNA(i)(Met) ternary complex and inhibit cancer cell proliferation. An optimization process was undertaken to improve their solubility while preserving their biological activity. Non-symmetrical hybrid ureas were generated by combining one of the hydrophobic phenyl moieties present in the symmetrical ureas with the polar 3-hydroxy-tolyl moiety. O-alkylation of the later added potentially solubilizing charge bearing groups. The new non-symmetrical N,N'-diarylureas were characterized by ternary complex reporter gene and cell proliferation assays, demonstrating good bioactivities. A representative sample of these compounds potently induced phosphorylation of eIF2 alpha and expression of CHOP at the protein and mRNA levels. These inhibitors of translation initiation may become leads for the development of potent, non-toxic, and target specific anti-cancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.126

文献信息

• N,N′-diarylurea compounds and N,N′-diarylthiourea compounds as inhibitors of translation initiation
  申请人：Aktas Bertal Huseyin

  公开号：US09421211B2

  公开（公告）日：2016-08-23

  Compositions and methods for inhibiting translation initiation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using N,N′-diarylureas and/or N,N′-diarylthiourea compounds are described.

  提供了用于抑制翻译起始的组合物和方法。描述了使用N,N′-二芳基脲和/或N,N′-二芳基硫脲化合物治疗（1）细胞增殖性疾病，（2）非增殖性、退行性疾病，（3）病毒感染和/或（4）与病毒感染相关的疾病的组合物、方法和试剂盒。