1-(4-氨基苯基)-1-甲基-3-苯基脲 | 1039976-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氨基苯基)-1-甲基-3-苯基脲
• 英文名称: 1-(4-aminophenyl)-1-methyl-3-phenylurea
• CAS: 1039976-40-3
• 化学式: C₁₄H₁₅N₃O
• 分子量: 241.293
• InChiKey: CEQLXUKJRSPFRX-UHFFFAOYSA-N

物化性质

• 沸点：
  496.5±37.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氨基苯基)-1-甲基-3-苯基脲 、 3-甲醛苯甲酸甲酯 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以49%的产率得到GN-6860
  参考文献：
  名称：

  Discovery of 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivatives as non-peptidic selective SUMO-sentrin specific protease (SENP)1 inhibitors

  摘要：

  We developed 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivative 4 (GN6958) as a non-peptidic selective SUMO-sentrin specific protease (SENP) 1 protease inhibitor based on the hypoxia inducible factor (HIF)-1 alpha inhibitor 1 (GN6767). The direct interaction of compound 1 with SENP1 protein in cells was observed by the pull-down experiments using the biotin-tagged compound 2 coated on the streptavidin affinity column. Among the various 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivatives tested, compounds 3 and 4 suppressed HIF-1 alpha accumulation in a concentration-dependent manner without affecting the expression level of tubulin protein in HeLa cells. Both compounds inhibited SENP1 protease activity in a concentration-dependent manner, and compound 4 exhibited more potent inhibition than compound 3. Compound 4 exhibited selective inhibition against SENP1 protease activity without inhibiting other protease enzyme activities in vitro. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.084
• 作为产物：
  描述：

  N-methyl-N-(4-nitrophenyl)carbamoyl chloride 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 1-(4-氨基苯基)-1-甲基-3-苯基脲
  参考文献：
  名称：

  Discovery of 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivatives as non-peptidic selective SUMO-sentrin specific protease (SENP)1 inhibitors

  摘要：

  We developed 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivative 4 (GN6958) as a non-peptidic selective SUMO-sentrin specific protease (SENP) 1 protease inhibitor based on the hypoxia inducible factor (HIF)-1 alpha inhibitor 1 (GN6767). The direct interaction of compound 1 with SENP1 protein in cells was observed by the pull-down experiments using the biotin-tagged compound 2 coated on the streptavidin affinity column. Among the various 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivatives tested, compounds 3 and 4 suppressed HIF-1 alpha accumulation in a concentration-dependent manner without affecting the expression level of tubulin protein in HeLa cells. Both compounds inhibited SENP1 protease activity in a concentration-dependent manner, and compound 4 exhibited more potent inhibition than compound 3. Compound 4 exhibited selective inhibition against SENP1 protease activity without inhibiting other protease enzyme activities in vitro. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.084

文献信息

• BENZENE DERIVATIVES AND MEDICINAL USE THEREOF
  申请人：Ajinomoto Co., Inc.

  公开号：EP1113000A1

  公开（公告）日：2001-07-04

  The present invention provides an AP-1 activation inhibitor, NF-kappa B activation inhibitor, inflammatory cytokine production inhibitor, matrix metalloprotease production inhibitor, inflammatory cell adhesion molecule expression inhibitor, anti-inflammatory agent, antirheumatic agent, immunosuppressant, cancer metastasis inhibitor, remedy for arteriosclerosis and antiviral agent which contain the benzene derivative of the following general formula (I) or a pharmaceutically acceptable salt thereof as an active ingredient.

  本发明提供了一种 AP-1 活化抑制剂、NF-kappa B 活化抑制剂、炎症细胞因子产生抑制剂、基质金属蛋白酶产生抑制剂、炎症细胞粘附分子表达抑制剂、抗炎剂、抗风湿剂、免疫抑制剂、癌症转移抑制剂、动脉硬化治疗剂和抗病毒剂，其活性成分含有下通式（I）的苯衍生物或其药学上可接受的盐。
• Benzene derivatives and Pharmaceutical use thereof
  申请人：Ajinomoto Co., Inc.

  公开号：US20010018441A1

  公开（公告）日：2001-08-30

  The present invention provides an AP-1 activation inhibitor, NF-kappa B activation inhibitor, inflammatory cytokine production inhibitor, matrix metalloprotease production inhibitor, inflammatory cell adhesion molecule expression inhibitor, anti-inflammatory agent, antirheumatic agent, immunosuppressant, cancer metastasis inhibitor, remedy for arteriosclerosis and antiviral agent which contain the benzene derivative of the following general formula (I) or a pharmaceutically acceptable salt thereof as an active ingredient. 1

  本发明提供了一种AP-1活化抑制剂、NF-kappa B活化抑制剂、炎症细胞因子产生抑制剂、基质金属蛋白酶产生抑制剂、炎症细胞粘附分子表达抑制剂、抗炎剂、抗风湿剂、免疫抑制剂、癌症转移抑制剂、动脉硬化治疗剂和抗病毒剂，其活性成分含有下通式（I）的苯衍生物或其药学上可接受的盐。 1
• Benzene derivatives and pharmaceutical use thereof
  申请人：AJINOMOTO CO., INC

  公开号：US20030166693A1

  公开（公告）日：2003-09-04

  The present invention provides an AP-1 activation inhibitor, NF-kappa B activation inhibitor, inflammatory cytokine production inhibitor, matrix metalloprotease production inhibitor, inflammatory cell adhesion molecule expression inhibitor, anti-inflammatory agent, antirheumatic agent, immunosuppressant, cancer metastasis inhibitor, remedy for arteriosclerosis and antiviral agent which contain the benzene derivative of the following general formula (I) or a pharmaceutically acceptable salt thereof as an active ingredient. 1

  本发明提供了一种AP-1活化抑制剂、NF-kappa B活化抑制剂、炎症细胞因子产生抑制剂、基质金属蛋白酶产生抑制剂、炎症细胞粘附分子表达抑制剂、抗炎剂、抗风湿剂、免疫抑制剂、癌症转移抑制剂、动脉硬化治疗剂和抗病毒剂，其活性成分含有下通式（I）的苯衍生物或其药学上可接受的盐。 1
• US6703379B2
  申请人：——

  公开号：US6703379B2

  公开（公告）日：2004-03-09
• US7459585B2
  申请人：——

  公开号：US7459585B2

  公开（公告）日：2008-12-02