N,N-diethyl-3-(1',5',6',7'-tetrahydrospiro[[1,3]dithiolane-2,4'-indole]-3'-yl)propanamide | 1239441-04-3

• 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-(1',5',6',7'-tetrahydrospiro[[1,3]dithiolane-2,4'-indole]-3'-yl)propanamide
• 英文别名: N,N-diethyl-3-spiro[1,3-dithiolane-2,4'-1,5,6,7-tetrahydroindole]-3'-ylpropanamide
• CAS: 1239441-04-3
• 化学式: C₁₇H₂₆N₂OS₂
• 分子量: 338.538
• InChiKey: YSVCMKUMCWPIBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-3-(1',5',6',7'-tetrahydrospiro[[1,3]dithiolane-2,4'-indole]-3'-yl)propanamide 在 lithium aluminium tetrahydride 、 水 、 calcium carbonate 、 mercury dichloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 3-[3-(diethylamino)propyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde
  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：

  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

文献信息

• 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.
• 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。