N-(2-methoxy-phenyl)-N'-(4-nitro-phenyl)-urea

• 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: N-(2-methoxy-phenyl)-N'-(4-nitro-phenyl)-urea
• 英文别名: N-(2-Methoxy-phenyl)-N'-(4-nitro-phenyl)-harnstoff；1-(2-Methoxyphenyl)-3-(4-nitrophenyl)urea
• 化学式: C₁₄H₁₃N₃O₄
• 分子量: 287.275
• InChiKey: SEHBBZWCARMWMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-methoxy-phenyl)-N'-(4-nitro-phenyl)-urea 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 C₁₄H₁₅N₃O₂
  参考文献：
  名称：

  Design, synthesis and evaluation of acridine derivatives as multi-target Src and MEK kinase inhibitors for anti-tumor treatment

  摘要：

  Clinical studies have shown enhanced anticancer effects of combined inhibition of Src and MEK kinases. Development of multi-target drugs against Src and MEK is of potential therapeutic advantage against cancers. As a follow-up of our previous studies, and by using molecular docking method, we designed and synthesized a new series of 9-anilinoacridines containing phenyl-urea moieties as potential novel dual Src and MEK inhibitors. The anti-proliferative assays against K562 and HepG-2 tumor cells showed that most of the derivatives displayed good cytotoxicity in vitro. In particular, kinase inhibition assays showed that compound 8m inhibited Src (59.67%) and MEK (43.23%) at 10 mu M, and displayed moderate inhibitory activity against ERK and AKT, the downstream effectors of both Src and MEK. Moreover, compound 8m was found to induce K562 cells apoptosis. Structure-activity relationships of these derivatives were analyzed. Our study suggested that acridine scaffold, particularly compound 8m, is of potential interest for developing novel multi-target Src and MEK kinase inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.011
• 作为产物：
  描述：

  4-硝基-苯甲酰基叠氮化物 在 甲苯 作用下， 生成 N-(2-methoxy-phenyl)-N'-(4-nitro-phenyl)-urea
  参考文献：
  名称：

  Sah, Recueil des Travaux Chimiques des Pays-Bas, 1940, vol. 59, p. 231,235

  摘要：

  DOI：

文献信息

• Cotarca, Livius; Bacaloglu, R.; Csunderlik, C., Journal fur praktische Chemie (Leipzig 1954), 1987, vol. 329, # 6, p. 1052 - 1062
  作者：Cotarca, Livius、Bacaloglu, R.、Csunderlik, C.、Marcu, N.、Tarnaveanu, A.

  DOI：——

  日期：——
• A comparative study of diaryl urea molecules with and without sulfonamide group on Carbonic anhydrase IX and XII inhibition and its consequence on breast cancer cells
  作者：Joy Debnath、Dhananjaya Keshamasetthy、Jacob Combs、Katherine Leon、Daniela Vullo、Abhijit Chatterjee、Robert McKenna、Claudiu T. Supuran

  DOI：10.1016/j.bioorg.2024.107192

  日期：2024.4
• Design, synthesis and evaluation of acridine derivatives as multi-target Src and MEK kinase inhibitors for anti-tumor treatment
  作者：Zhishan Cui、Xi Li、Lulu Li、Bin Zhang、Chunmei Gao、Yuzong Chen、Chunyan Tan、Hongxia Liu、Weiyi Xie、Ti Yang、Yuyang Jiang

  DOI：10.1016/j.bmc.2015.12.011

  日期：2016.1

  Clinical studies have shown enhanced anticancer effects of combined inhibition of Src and MEK kinases. Development of multi-target drugs against Src and MEK is of potential therapeutic advantage against cancers. As a follow-up of our previous studies, and by using molecular docking method, we designed and synthesized a new series of 9-anilinoacridines containing phenyl-urea moieties as potential novel dual Src and MEK inhibitors. The anti-proliferative assays against K562 and HepG-2 tumor cells showed that most of the derivatives displayed good cytotoxicity in vitro. In particular, kinase inhibition assays showed that compound 8m inhibited Src (59.67%) and MEK (43.23%) at 10 mu M, and displayed moderate inhibitory activity against ERK and AKT, the downstream effectors of both Src and MEK. Moreover, compound 8m was found to induce K562 cells apoptosis. Structure-activity relationships of these derivatives were analyzed. Our study suggested that acridine scaffold, particularly compound 8m, is of potential interest for developing novel multi-target Src and MEK kinase inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.
• Sah, Recueil des Travaux Chimiques des Pays-Bas, 1940, vol. 59, p. 231,235
  作者：Sah

  DOI：——

  日期：——