1-(4-nitrophenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one | 163083-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-nitrophenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one
• 英文别名: 2,6,6-Trimethyl-1-(4-nitrophenyl)-5,7-dihydroindol-4-one
• CAS: 163083-12-3
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: CRWLTASCPOCPON-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  472.0±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one 在 sodium azide 、 硫酸 作用下， 反应 2.0h， 以73%的产率得到1-(4-nitrophenyl)-2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindole 3-sulfonic acid
  参考文献：
  名称：

  施密特条件下 1-(4-R-Phenyl)-2.6,6-trimethyl-4-oxo-4,5,6,7-四氢吲哚的异常磺化

  摘要：

  摘要 意外的 4-氧-四氢吲哚 3-磺酸是使用叠氮化钠和硫酸（施密特条件）从其相应的 4-氧-四氢吲哚合成的。

  DOI：

  10.1080/00397919508012669
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 potassium carbonate 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 60.0h， 生成 1-(4-nitrophenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one
  参考文献：
  名称：

  Tetrahydropyrrolo[3,2-c]azepin-4-ones as a new class of cytotoxic compounds

  摘要：

  Pyrroloazepinones 8a-j and 9a-j were designed by structural modification of lead compound 3. These compounds were tested on five tumor cell lines to determine the role of the azeto ring and the 2-methyl substituent in the cytotoxicity of compound 3. Our results show that compounds 8a-j (R-1 = CH3) have dramatically reduced cytotoxicity, resulting from the loss of the azeto moiety of lead compound 3. By contrast, azepinones 9a-j (R-1 = 4-nitrophenyl) inhibited the proliferation of almost all cancer cell lines tested even though they lack the azeto ring. Preliminary SAR studies with these compounds revealed the importance of halogens at the para- or meta-position of the 1-phenyl moiety. Additionally, derivatives 9a (R-2 = H), 9e (R-2 = 4-F), and 9g (R-2 = 4-OMe) were selectively cytotoxic to U-251 cells. However, none of the pyrroloazepinones inhibited the enzymatic activity of CDK1/cyclin B, CDK5/p25, and GSK-3. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.012

文献信息

• Martinez Roberto, Avila Gustavo Z., Reyes A. Eduardo, Synth. Commun, 25 (1995) N 7, S 1071-1076
  作者：Martinez Roberto, Avila Gustavo Z., Reyes A. Eduardo

  DOI：——

  日期：——
• Tetrahydropyrrolo[3,2-c]azepin-4-ones as a new class of cytotoxic compounds
  作者：Roberto Martínez、J. Gustavo Ávila、Ma. Teresa Ramírez、Araceli Pérez、Ángeles Martínez

  DOI：10.1016/j.bmc.2006.02.012

  日期：2006.6

  Pyrroloazepinones 8a-j and 9a-j were designed by structural modification of lead compound 3. These compounds were tested on five tumor cell lines to determine the role of the azeto ring and the 2-methyl substituent in the cytotoxicity of compound 3. Our results show that compounds 8a-j (R-1 = CH3) have dramatically reduced cytotoxicity, resulting from the loss of the azeto moiety of lead compound 3. By contrast, azepinones 9a-j (R-1 = 4-nitrophenyl) inhibited the proliferation of almost all cancer cell lines tested even though they lack the azeto ring. Preliminary SAR studies with these compounds revealed the importance of halogens at the para- or meta-position of the 1-phenyl moiety. Additionally, derivatives 9a (R-2 = H), 9e (R-2 = 4-F), and 9g (R-2 = 4-OMe) were selectively cytotoxic to U-251 cells. However, none of the pyrroloazepinones inhibited the enzymatic activity of CDK1/cyclin B, CDK5/p25, and GSK-3. (c) 2006 Elsevier Ltd. All rights reserved.
• Unusual Sulfonation of 1-(4-R-Phenyl)-2.6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindoles Under Schmidt Conditions
  作者：Roberto Martínez、Gustavo Avila、Eduardo Reyes

  DOI：10.1080/00397919508012669

  日期：1995.4

  Abstract Unexpected 4-oxo-tetrahydroindoles 3-sulfonic acids were synthesized from their corresponding 4-oxo-tetrahydroindoles using sodium azide and sulfuric acid (Schmidt conditions).

  摘要 意外的 4-氧-四氢吲哚 3-磺酸是使用叠氮化钠和硫酸（施密特条件）从其相应的 4-氧-四氢吲哚合成的。