N,N-diethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanamide | 258831-31-1

• 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: N,N-diethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanamide
• 英文别名: N,N-diethyl-3-(4-oxo-1,5,6,7-tetrahydroindol-3-yl)propanamide
• CAS: 258831-31-1
• 化学式: C₁₅H₂₂N₂O₂
• 分子量: 262.352
• InChiKey: ONGJIUTYNDTROX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanamide 在 甲醇 、 三氟化硼乙醚 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 17.25h， 生成 N,N-diethyl-3-(1',5',6',7'-tetrahydrospiro[[1,3]dithiolane-2,4'-indole]-3'-yl)propanamide
  参考文献：
  名称：

  Design and synthesis of pyrrole–5-(2,6-dichlorobenzyl)sulfonylindolin-2-ones with C-3′ side chains as potent Met kinase inhibitors

  摘要：

  亚纳摩尔级别的Met抑制剂。

  DOI：

  10.1039/c4ra08720h
• 作为产物：
  描述：

  、 二乙胺 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N,N-diethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanamide
  参考文献：
  名称：

  Discovery of Pyrrole−Indoline-2-ones as Aurora Kinase Inhibitors with a Different Inhibition Profile

  摘要：

  A series of pyrrole-indolin-2-ones were synthesized, and their inhibition profile for Aurora kinases was studied. The potent compound 33 with phenylsulfonamido at the C-5 position and a carboxyethyl group at the C-3' position selectively inhibited Aurora A over Aurora B with IC(50) values of 12 and 156 nM, respectively. Replacement of the carboxyl group with an amino group led to compound 47, which retained the activity for Aurora B and lost activity for Aurora A (IC(50) = 2.19 mu M). Computation modeling was used to address the different inhibition profiles of 33 and 47. Compounds 47 and 36 (the ethyl ester analogue of 33) inhibited the proliferation of HCT-116 and HT-29 cells and suppressed levels of the phosphorylated substrates of Aurora A and Aurora B in the Western blots.

  DOI：

  10.1021/jm1001869

文献信息

• 3-methylidenyl-2-indolinone modulators of protein kinase
  申请人：Sugen, Inc.

  公开号：US20040024010A1

  公开（公告）日：2004-02-05

  The present invention relates to novel 3-methylidenyl-2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及新型的3-甲基亚烯基-2-吲哚酮化合物及其生理上可接受的盐和前药，这些化合物可调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用途。
• US6531502B1
  申请人：——

  公开号：US6531502B1

  公开（公告）日：2003-03-11
• US6855730B2
  申请人：——

  公开号：US6855730B2

  公开（公告）日：2005-02-15
• Design and synthesis of pyrrole–5-(2,6-dichlorobenzyl)sulfonylindolin-2-ones with C-3′ side chains as potent Met kinase inhibitors
  作者：Chia-Wei Liu、Chun-Liang Lai、Yu-Hsiang Lin、Li-Wei Teng、Sheng-chuan Yang、Win-Yin Wei、Shu Fu Lin、Ju-Ying Yang、Hung-Jyun Huang、Ru-Wen Wang、Chao-Cheng Chiang、Mei-Hui Lee、Yu-Chuan Wang、Shih-Hsien Chuang、Jia-Ming Chang、Ying-Shuan E. Lee、Jiann-Jyh Huang

  DOI：10.1039/c4ra08720h

  日期：——

  Subnanomolar Met inhibitors.

  亚纳摩尔级别的Met抑制剂。
• Discovery of Pyrrole−Indoline-2-ones as Aurora Kinase Inhibitors with a Different Inhibition Profile
  作者：Chao-Cheng Chiang、Yu-Hsiang Lin、Shu Fu Lin、Chun-Liang Lai、Chiawei Liu、Win-Yin Wei、Sheng-chuan Yang、Ru-Wen Wang、Li-Wei Teng、Shih-Hsien Chuang、Jia-Ming Chang、Ta-Tung Yuan、Ying-Shuen Lee、Paonien Chen、Wei-Kuang Chi、Ju-Ying Yang、Hung-Jyun Huang、Chu-Bin Liao、Jiann-Jyh Huang

  DOI：10.1021/jm1001869

  日期：2010.8.26

  A series of pyrrole-indolin-2-ones were synthesized, and their inhibition profile for Aurora kinases was studied. The potent compound 33 with phenylsulfonamido at the C-5 position and a carboxyethyl group at the C-3' position selectively inhibited Aurora A over Aurora B with IC(50) values of 12 and 156 nM, respectively. Replacement of the carboxyl group with an amino group led to compound 47, which retained the activity for Aurora B and lost activity for Aurora A (IC(50) = 2.19 mu M). Computation modeling was used to address the different inhibition profiles of 33 and 47. Compounds 47 and 36 (the ethyl ester analogue of 33) inhibited the proliferation of HCT-116 and HT-29 cells and suppressed levels of the phosphorylated substrates of Aurora A and Aurora B in the Western blots.