GN-6860 | 1392278-31-7

• 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: GN-6860
• 英文别名: methyl 3-[4-(1-methyl-3-phenylureido)phenylaminomethyl]benzoate；Methyl 3-[[4-[methyl(phenylcarbamoyl)amino]anilino]methyl]benzoate
• CAS: 1392278-31-7
• 化学式: C₂₃H₂₃N₃O₃
• 分子量: 389.454
• InChiKey: QZAVBGJBMLGHFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-methyl-N-(4-nitrophenyl)carbamoyl chloride 在 5%-palladium/activated carbon 、 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 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

文献信息

• Discovery of 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivatives as non-peptidic selective SUMO-sentrin specific protease (SENP)1 inhibitors
  作者：Masaharu Uno、Yosuke Koma、Hyun Seung Ban、Hiroyuki Nakamura

  DOI：10.1016/j.bmcl.2012.06.084

  日期：2012.8

  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.