benzyl (4S)-4-[2-(1-hexyl-4-nitroindol-3-yl)ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 1004551-09-0

• 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: benzyl (4S)-4-[2-(1-hexyl-4-nitroindol-3-yl)ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1004551-09-0
• 化学式: C₂₉H₃₇N₃O₅
• 分子量: 507.63
• InChiKey: SBDAJZHTHUFPTR-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4S)-4-[2-(1-hexyl-4-nitroindol-3-yl)ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到benzyl N-[(2S)-4-(1-hexyl-4-nitroindol-3-yl)-1-hydroxybutan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Biological Evaluation of 1-Hexylindolactam-V10 as a Selective Activator for Novel Protein Kinase C Isozymes

  摘要：

  Conventional and novel protein kinase C (PKC) isozymes are the main targets of tumor promoters. We developed 1-hexylindolactam-V10 (5) as a selective activator for novel PKC isozymes that play important roles in various cellular processes related to tumor promotion, ischemia-reperfusion injury in the heart, and Alzheimer's disease. The compound existed as a mixture of three conformers. The trans-amide restricted analogues of 5 (14 and 15) hardly bound to PKC isozymes, suggesting that the active conformation of 5 could be that with a cis-amide. Compound 5 selectively translocated novel PKC isozymes over conventional PKC isozymes in HeLa cells at 0.1-1 mu M. These results suggest that 5 could be useful for the functional analysis of novel PKC isozymes.

  DOI：

  10.1021/jm0706719
• 作为产物：
  描述：

  benzyl (4S)-4-[(E)-2-(1-hexyl-4-nitroindol-3-yl)ethenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 2,4,6-三异丙基苯磺酰基肼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以74%的产率得到benzyl (4S)-4-[2-(1-hexyl-4-nitroindol-3-yl)ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Biological Evaluation of 1-Hexylindolactam-V10 as a Selective Activator for Novel Protein Kinase C Isozymes

  摘要：

  Conventional and novel protein kinase C (PKC) isozymes are the main targets of tumor promoters. We developed 1-hexylindolactam-V10 (5) as a selective activator for novel PKC isozymes that play important roles in various cellular processes related to tumor promotion, ischemia-reperfusion injury in the heart, and Alzheimer's disease. The compound existed as a mixture of three conformers. The trans-amide restricted analogues of 5 (14 and 15) hardly bound to PKC isozymes, suggesting that the active conformation of 5 could be that with a cis-amide. Compound 5 selectively translocated novel PKC isozymes over conventional PKC isozymes in HeLa cells at 0.1-1 mu M. These results suggest that 5 could be useful for the functional analysis of novel PKC isozymes.

  DOI：

  10.1021/jm0706719

文献信息

• Synthesis, Conformational Analysis, and Biological Evaluation of 1-Hexylindolactam-V10 as a Selective Activator for Novel Protein Kinase C Isozymes
  作者：Ryo C. Yanagita、Yu Nakagawa、Nobuhiro Yamanaka、Kaori Kashiwagi、Naoaki Saito、Kazuhiro Irie

  DOI：10.1021/jm0706719

  日期：2008.1.1

  Conventional and novel protein kinase C (PKC) isozymes are the main targets of tumor promoters. We developed 1-hexylindolactam-V10 (5) as a selective activator for novel PKC isozymes that play important roles in various cellular processes related to tumor promotion, ischemia-reperfusion injury in the heart, and Alzheimer's disease. The compound existed as a mixture of three conformers. The trans-amide restricted analogues of 5 (14 and 15) hardly bound to PKC isozymes, suggesting that the active conformation of 5 could be that with a cis-amide. Compound 5 selectively translocated novel PKC isozymes over conventional PKC isozymes in HeLa cells at 0.1-1 mu M. These results suggest that 5 could be useful for the functional analysis of novel PKC isozymes.