methyl 5-[[3-[(3-methoxycarbonyl-1H-indol-5-yl)amino]-3-oxopropanoyl]amino]-1H-indole-3-carboxylate | 1408083-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 5-[[3-[(3-methoxycarbonyl-1H-indol-5-yl)amino]-3-oxopropanoyl]amino]-1H-indole-3-carboxylate
• CAS: 1408083-19-1
• 化学式: C₂₃H₂₀N₄O₆
• 分子量: 448.435
• InChiKey: UPRMQSGAWIRNLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-[[3-[(3-methoxycarbonyl-1H-indol-5-yl)amino]-3-oxopropanoyl]amino]-1H-indole-3-carboxylate 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以25%的产率得到5-[[3-[(3-carboxy-1H-indol-5-yl)amino]-3-oxopropanoyl]amino]-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Identification of Small-Molecule Enhancers of Arginine Methylation Catalyzed by Coactivator-Associated Arginine Methyltransferase 1

  摘要：

  Arginine methylation, is a common post-translational modification that is crucial in modulating gene expression at multiple critical. levels. The arginine methyltransferases (PRMTs) are envisaged as promising druggable targets,: but their role in physiological and pathological pathways is far from being clear due to the limited number of modulators reported to date. In this effort; enzyme activators can be invaluable tools, useful as gain-of-function reagents to interrogate the biological roles. in cells and in vivo of PRMTs. Yet the identification such molecule's is rarely pursued. Herein we describe a series of aryl ureido acetamido indole carboxylates (dubbed "uracandolates"), able to increase the Methylation of histone (H3) or nonhistone (polyadenylate-bihding protein 1, PABP1) substrates induced by coactivator-associated arginine methyltransferase 1 (CARM1), bath in in vitro and cellular settings. To the best of our knowledge, this is the first report of compounds acting as CARM1 activators.

  DOI：

  10.1021/jm301097p
• 作为产物：
  描述：

  5-硝基-1H-吲哚-3-羧酸甲酯 在 5%-palladium/activated carbon 、 氢气 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 甲苯 为溶剂， 20.0~120.0 ℃ 、1.72 MPa 条件下， 反应 3.0h， 生成 methyl 5-[[3-[(3-methoxycarbonyl-1H-indol-5-yl)amino]-3-oxopropanoyl]amino]-1H-indole-3-carboxylate
  参考文献：
  名称：

  Identification of Small-Molecule Enhancers of Arginine Methylation Catalyzed by Coactivator-Associated Arginine Methyltransferase 1

  摘要：

  Arginine methylation, is a common post-translational modification that is crucial in modulating gene expression at multiple critical. levels. The arginine methyltransferases (PRMTs) are envisaged as promising druggable targets,: but their role in physiological and pathological pathways is far from being clear due to the limited number of modulators reported to date. In this effort; enzyme activators can be invaluable tools, useful as gain-of-function reagents to interrogate the biological roles. in cells and in vivo of PRMTs. Yet the identification such molecule's is rarely pursued. Herein we describe a series of aryl ureido acetamido indole carboxylates (dubbed "uracandolates"), able to increase the Methylation of histone (H3) or nonhistone (polyadenylate-bihding protein 1, PABP1) substrates induced by coactivator-associated arginine methyltransferase 1 (CARM1), bath in in vitro and cellular settings. To the best of our knowledge, this is the first report of compounds acting as CARM1 activators.

  DOI：

  10.1021/jm301097p