6H-1-phenyl-2,7,7-trimethyl-4,5,7,8-tetrahydropyrrolo[3,2-c]azepin-4-one | 164226-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 6H-1-phenyl-2,7,7-trimethyl-4,5,7,8-tetrahydropyrrolo[3,2-c]azepin-4-one
• 英文别名: 5,6,7,8-tetrahydro-2,7,7-trimethyl-1-phenylpyrrolo[3,2-c]azepin-4(1H)-one；2,7,7-trimethyl-1-phenyl-6,8-dihydro-5H-pyrrolo[3,2-c]azepin-4-one
• CAS: 164226-58-8
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: VMSHQQHMBFSTRS-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C
• 沸点：
  499.1±34.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 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：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6H-1-phenyl-2,7,7-trimethyl-4,5,7,8-tetrahydropyrrolo[3,2-c]azepin-4-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以87%的产率得到6H-1-phenyl-2,7,7-trimethyl-4,5,7,8-tetrahydropyrrolo[3,2-c]azepin-4-thione
  参考文献：
  名称：

  Synthesis of the New Triheterocyclic System C3N-C4N-C6N. 3-Aryl-2,5,5-trimethyl-9a-methylsulfanyl-9-phenoxy-4,5,6,8,9,9a-hexahydro-3H-azeto[1,2-a]pyrrolo[3,2-c]azepin-8-ones

  摘要：

  The regio- and stereoselective synthesis of the cis-3-aryl-2,5,5-trimethyl-9a-methylsulfanyl-9-phenoxy-4,5,6,8,9,9a-hexahydro-3H-azeto[1,2-a]pyrrolo[3,2-c]azepin-8-ones (1) was performed. A four-step sequence, which yields are good, constitutes the first synthetic way for the preparation of the first member of this new C3N-C4N-C6N series.

  DOI：

  10.3987/com-99-8662
• 作为产物：
  描述：

  5,5-dimethyl-2-(2-oxopropyl)cyclohexane-1,3-dione 在 磷酸酐 、 sodium hydroxide 、 磷酸 、 盐酸羟胺 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 6H-1-phenyl-2,7,7-trimethyl-4,5,7,8-tetrahydropyrrolo[3,2-c]azepin-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

• Synthesis and spectral properties of 6<i>H</i>-1-(2-, 3- and 4-<i>R</i>-Phenyl)-2,7,7-trimethyl-4,5,7,8-tetrahydropyrrolo[3,2-<i>c</i>]azepin-4-ones
  作者：Roberto Martínez、Gema López、Avila Z. J. Gustavo

  DOI：10.1002/jhet.5570320218

  日期：1995.3

  The preparation of novel 4,5,7,8-tetrahydropyrrolo[3,2-c]azepin-4-ones is described. The structure of all the products was corroborated by ir, mass spectrometry and 1H and 13C-nmr.

  描述了新型4,5,7,8-四氢吡咯并[3,2 - c ] azepin-4-ones的制备。所有产品的结构均通过红外，质谱和1 H和13 C-nmr证实。
• 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.
• Synthesis of the New Triheterocyclic System C3N-C4N-C6N. 3-Aryl-2,5,5-trimethyl-9a-methylsulfanyl-9-phenoxy-4,5,6,8,9,9a-hexahydro-3H-azeto[1,2-a]pyrrolo[3,2-c]azepin-8-ones
  作者：Roberto Martínez、José Gustavo Avila-Zárraga、Gema López-López、Víctor Oswaldo Nava-Salgado

  DOI：10.3987/com-99-8662

  日期：——

  The regio- and stereoselective synthesis of the cis-3-aryl-2,5,5-trimethyl-9a-methylsulfanyl-9-phenoxy-4,5,6,8,9,9a-hexahydro-3H-azeto[1,2-a]pyrrolo[3,2-c]azepin-8-ones (1) was performed. A four-step sequence, which yields are good, constitutes the first synthetic way for the preparation of the first member of this new C3N-C4N-C6N series.