3-isopropylamino-5-phenylcyclohex-2-enone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isopropylamino-5-phenylcyclohex-2-enone
• 英文别名: 5-Phenyl-3-(propan-2-ylamino)cyclohex-2-en-1-one
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: KDLWBWCNVNESPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-isopropylamino-5-phenylcyclohex-2-enone 在 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 5-isopropyl-7-phenyl-5,6,7,8-tetrahydroindeno[1,2-b]indole-9,10-dione
  参考文献：
  名称：

  Synthesis, Biological Evaluation and Molecular Modeling of Substituted Indeno[1,2-b]indoles as Inhibitors of Human Protein Kinase CK2

  摘要：

  由于其环状的6-5-5-6成员环结构，吲哚吲哚烯引起了人类CK2 ATP竞争性抑制剂设计的极大兴趣。本研究中，我们制备了二十一种吲哚[1,2-b]吲哚衍生物，并对它们进行了体外人类CK2的测试。吲哚吲哚酮5a和5b对人类CK2的抑制作用分别为IC50值0.17和0.61 µM。吲哚[1,2-b]吲哚醌7a在亚微摩尔范围内亦显示出对CK2的抑制活性（IC50 = 0.43 µM）。此外，还评估了大量吲哚吲哚烯衍生物对细胞系3T3、WI-38、HEK293T和MEF的细胞毒性活性。

  DOI：

  10.3390/ph8020279
• 作为产物：
  描述：

  5-phenyl-cyclohexane-1,3-dione 、 异丙胺 以 甲苯 为溶剂， 反应 6.0h， 以100%的产率得到3-isopropylamino-5-phenylcyclohex-2-enone
  参考文献：
  名称：

  Synthesis, Biological Evaluation and Molecular Modeling of Substituted Indeno[1,2-b]indoles as Inhibitors of Human Protein Kinase CK2

  摘要：

  由于其环状的6-5-5-6成员环结构，吲哚吲哚烯引起了人类CK2 ATP竞争性抑制剂设计的极大兴趣。本研究中，我们制备了二十一种吲哚[1,2-b]吲哚衍生物，并对它们进行了体外人类CK2的测试。吲哚吲哚酮5a和5b对人类CK2的抑制作用分别为IC50值0.17和0.61 µM。吲哚[1,2-b]吲哚醌7a在亚微摩尔范围内亦显示出对CK2的抑制活性（IC50 = 0.43 µM）。此外，还评估了大量吲哚吲哚烯衍生物对细胞系3T3、WI-38、HEK293T和MEF的细胞毒性活性。

  DOI：

  10.3390/ph8020279

文献信息

• Screening of indeno[1,2-<i>b</i>]indoloquinones by MALDI-MS: a new set of potential CDC25 phosphatase inhibitors brought to light
  作者：Faten Alchab、Estelle Sibille、Laurent Ettouati、Emilie Bana、Zouhair Bouaziz、Angélique Mularoni、Elodie Monniot、Denyse Bagrel、Joachim Jose、Marc Le Borgne、Patrick Chaimbault

  DOI：10.1080/14756366.2016.1201480

  日期：2016.11.3

  Quinones and quinones-like compounds are potential candidates for the inhibition of CDC25 phosphatases. The combination of MALDI-MS analyses and biological studies was used to develop a rapid screening of a targeted library of indeno[1,2-b]indoloquinone derivatives. The screening protocol using MALDI-TOFMS and MALDI-FTICRMS highlighted four new promising candidates. Biological investigations showed that only compounds 5c-f inhibited CDC25A and -C phosphatases, with IC50 values around the micromolar range. The direct use of a screening method based on MALDI-MS technology allowed achieving fast scaffold identification of a new class of potent inhibitors of CDC25 phosphatases. These four molecules appeared as novel molecules of a new class of CDC25 inhibitors. Assessment of 5c-e in an MRC5 proliferation assay provided an early indicator of toxicity to mammalian cells. Compound 5d seems the most promising hit for developing new CDC25 inhibitors.
• Synthesis, Biological Evaluation and Molecular Modeling of Substituted Indeno[1,2-b]indoles as Inhibitors of Human Protein Kinase CK2
  作者：Faten Alchab、Laurent Ettouati、Zouhair Bouaziz、Andre Bollacke、Jean-Guy Delcros、Christoph Gertzen、Holger Gohlke、Noël Pinaud、Mathieu Marchivie、Jean Guillon、Bernard Fenet、Joachim Jose、Marc Borgne

  DOI：10.3390/ph8020279

  日期：——

  Due to their system of annulated 6-5-5-6-membered rings, indenoindoles have sparked great interest for the design of ATP-competitive inhibitors of human CK2. In the present study, we prepared twenty-one indeno[1,2-b]indole derivatives, all of which were tested in vitro on human CK2. The indenoindolones 5a and 5b inhibited human CK2 with an IC50 of 0.17 and 0.61 µM, respectively. The indeno[1,2-b]indoloquinone 7a also showed inhibitory activity on CK2 at a submicromolar range (IC50 = 0.43 µM). Additionally, a large number of indenoindole derivatives was evaluated for their cytotoxic activities against the cell lines 3T3, WI-38, HEK293T and MEF.

  由于其环状的6-5-5-6成员环结构，吲哚吲哚烯引起了人类CK2 ATP竞争性抑制剂设计的极大兴趣。本研究中，我们制备了二十一种吲哚[1,2-b]吲哚衍生物，并对它们进行了体外人类CK2的测试。吲哚吲哚酮5a和5b对人类CK2的抑制作用分别为IC50值0.17和0.61 µM。吲哚[1,2-b]吲哚醌7a在亚微摩尔范围内亦显示出对CK2的抑制活性（IC50 = 0.43 µM）。此外，还评估了大量吲哚吲哚烯衍生物对细胞系3T3、WI-38、HEK293T和MEF的细胞毒性活性。