ethyl 5-[[2-[(4-methylphenyl)carbamoylamino]acetyl]amino]-1H-indole-2-carboxylate | 1408083-37-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 5-[[2-[(4-methylphenyl)carbamoylamino]acetyl]amino]-1H-indole-2-carboxylate
• CAS: 1408083-37-3
• 化学式: C₂₁H₂₂N₄O₄
• 分子量: 394.43
• InChiKey: UJJKORICSQAZGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	ethyl 5-(2-((tert-butoxycarbonyl)amino)acetamido)-1H-indole-2-carboxylate	1408083-98-6	C18H23N3O5	361.398
  5-氨基吲哚-2-甲酸乙酯	ethyl 5-amino-1H-indole-2-carboxylate	71086-99-2	C11H12N2O2	204.228

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-[[2-[(4-methylphenyl)carbamoylamino]acetyl]amino]-1H-indole-2-carboxylic acid	1408083-52-2	C19H18N4O4	366.376

反应信息

• 作为反应物：
  描述：

  ethyl 5-[[2-[(4-methylphenyl)carbamoylamino]acetyl]amino]-1H-indole-2-carboxylate 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以96%的产率得到5-[[2-[(4-methylphenyl)carbamoylamino]acetyl]amino]-1H-indole-2-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-氨基吲哚-2-甲酸乙酯 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 5-[[2-[(4-methylphenyl)carbamoylamino]acetyl]amino]-1H-indole-2-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