N-(2-oxoindolin-5-yl)-1-phenylmethanesulfonamide | 921812-49-9

• 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: N-(2-oxoindolin-5-yl)-1-phenylmethanesulfonamide
• 英文别名: N-(2-oxo-1,3-dihydroindol-5-yl)-1-phenylmethanesulfonamide
• CAS: 921812-49-9
• 化学式: C₁₅H₁₄N₂O₃S
• 分子量: 302.354
• InChiKey: LAGAEWCMNROKCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoate 、 N-(2-oxoindolin-5-yl)-1-phenylmethanesulfonamide 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (Z)-ethyl 3-(4-oxo-2-((2-oxo-5-(phenylmethylsulfonamido)indolin-3-ylidene)methyl)-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoate
  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
• 作为产物：
  描述：

  5-硝基-1,3-二氢-2H-吲哚-2-酮 在 吡啶 、 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 13.2h， 生成 N-(2-oxoindolin-5-yl)-1-phenylmethanesulfonamide
  参考文献：
  名称：

  新型 1, 3-二氢-2H-二氢吲哚-2-酮衍生物的设计、合成和 COX-2 抑制活性评价

  摘要：

  通过Knoevenagel缩合反应设计并合成了33种带有α,β-不饱和酮的1, 3-二氢-2H-二氢吲哚-2-酮衍生物。评估了所有化合物的细胞毒性、体外抗炎能力和体外COX-2抑制活性。化合物4a、4e、4i-4j和9d在LPS刺激的RAW 264.7细胞中表现出弱细胞毒性和不同程度的NO产生抑制作用。化合物4a、4i和4j的IC50值分别为17.81±1.86μM、20.41±1.61μM和16.31±0.35μM。化合物4e和9d表现出更好的抗炎活性，IC50值分别为13.51±0.48μM和10.03±0.27μM，低于阳性对照吡咯烷二硫代氨基甲酸铵(PDTC)。化合物 4e、9h、和9i表现出良好的COX-2抑制活性，IC50值分别为2.35±0.04μM、2.422±0.10μM和3.34±0.05μM。此外，通过分子对接预测了COX-2识别4e、9h和9i的可能机制。本研究结果

  DOI：

  10.3390/molecules28124668

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, Synthesis, and Evaluation of the COX-2 Inhibitory Activities of New 1,3-Dihydro-2H-indolin-2-one Derivatives
  作者：Taohua Pan、Maofei He、Lulu Deng、Jiang Li、Yanhua Fan、Xiaojiang Hao、Shuzhen Mu

  DOI：10.3390/molecules28124668

  日期：——

  Thirty-three 1, 3-dihydro-2H-indolin-2-one derivatives bearing α, β-unsaturated ketones were designed and synthesized via the Knoevenagel condensation reaction. The cytotoxicity, in vitro anti-inflammatory ability, and in vitro COX-2 inhibitory activity of all the compounds were evaluated. Compounds 4a, 4e, 4i-4j, and 9d exhibited weak cytotoxicity and different degrees of inhibition against NO production

  通过Knoevenagel缩合反应设计并合成了33种带有α,β-不饱和酮的1, 3-二氢-2H-二氢吲哚-2-酮衍生物。评估了所有化合物的细胞毒性、体外抗炎能力和体外COX-2抑制活性。化合物4a、4e、4i-4j和9d在LPS刺激的RAW 264.7细胞中表现出弱细胞毒性和不同程度的NO产生抑制作用。化合物4a、4i和4j的IC50值分别为17.81±1.86μM、20.41±1.61μM和16.31±0.35μM。化合物4e和9d表现出更好的抗炎活性，IC50值分别为13.51±0.48μM和10.03±0.27μM，低于阳性对照吡咯烷二硫代氨基甲酸铵(PDTC)。化合物 4e、9h、和9i表现出良好的COX-2抑制活性，IC50值分别为2.35±0.04μM、2.422±0.10μM和3.34±0.05μM。此外，通过分子对接预测了COX-2识别4e、9h和9i的可能机制。本研究结果