Diethyl 2-[(2-bromo-6-nitrophenyl)methyl]propanedioate | 887906-16-3

• 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: Diethyl 2-[(2-bromo-6-nitrophenyl)methyl]propanedioate
• CAS: 887906-16-3
• 化学式: C₁₄H₁₆BrNO₆
• 分子量: 374.188
• InChiKey: QLDAHEDCJGERQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl 2-[(2-bromo-6-nitrophenyl)methyl]propanedioate 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 锂硼氢 、 氯化亚砜 、 硼烷 、 氢气 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 71.5h， 生成 benzyl (2S)-2-[2-[(3S)-3-cyano-3-[[(1R)-2-hydroxy-1-phenylethyl]amino]propyl]-N-methyl-3-octylanilino]-3-methylbutanoate
  参考文献：
  名称：

  Design and Synthesis of 8-Octyl-benzolactam-V9, a Selective Activator for Protein Kinase Cε and η

  摘要：

  Conventional (alpha, beta I, beta II, gamma) and novel (delta, epsilon, eta, theta) protein kinase C (PKC) isozymes are main targets of tumor promoters, such as phorbol esters and indolactam-V ( ILV). We have recently found that 1-hexyl derivatives of indolinelactam-V ( 2, 3), in which the indole ring of ILV was replaced with the indoline ring, showed a binding preference for novel PKCs over conventional PKCs. To develop a new ILV analogue displaying increased synthetic accessibility and improved binding selectivity for novel PKCs, we have designed 8-octyl-benzolactam-V9 ( 4), a simple analogue without the pyrrolidine moiety of 2 and 3. Compound 4 showed significant binding selectivity for isolated C1B domains of novel PKCs. Moreover, 4 translocated PKC epsilon and eta from the cytoplasm to the plasma membrane of HeLa cells at 1 mu M, whereas other PKC isozymes did not respond even at 10 mu M. These results indicate that 4 could be a selective activator for PKC epsilon and eta.

  DOI：

  10.1021/jm050857c
• 作为产物：
  描述：

  2-溴-6-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.17h， 生成 Diethyl 2-[(2-bromo-6-nitrophenyl)methyl]propanedioate
  参考文献：
  名称：

  Design and Synthesis of 8-Octyl-benzolactam-V9, a Selective Activator for Protein Kinase Cε and η

  摘要：

  Conventional (alpha, beta I, beta II, gamma) and novel (delta, epsilon, eta, theta) protein kinase C (PKC) isozymes are main targets of tumor promoters, such as phorbol esters and indolactam-V ( ILV). We have recently found that 1-hexyl derivatives of indolinelactam-V ( 2, 3), in which the indole ring of ILV was replaced with the indoline ring, showed a binding preference for novel PKCs over conventional PKCs. To develop a new ILV analogue displaying increased synthetic accessibility and improved binding selectivity for novel PKCs, we have designed 8-octyl-benzolactam-V9 ( 4), a simple analogue without the pyrrolidine moiety of 2 and 3. Compound 4 showed significant binding selectivity for isolated C1B domains of novel PKCs. Moreover, 4 translocated PKC epsilon and eta from the cytoplasm to the plasma membrane of HeLa cells at 1 mu M, whereas other PKC isozymes did not respond even at 10 mu M. These results indicate that 4 could be a selective activator for PKC epsilon and eta.

  DOI：

  10.1021/jm050857c

文献信息

• Design and Synthesis of 8-Octyl-benzolactam-V9, a Selective Activator for Protein Kinase Cε and η
  作者：Yu Nakagawa、Kazuhiro Irie、Ryo C. Yanagita、Hajime Ohigashi、Ken-ichiro Tsuda、Kaori Kashiwagi、Naoaki Saito

  DOI：10.1021/jm050857c

  日期：2006.5.1

  Conventional (alpha, beta I, beta II, gamma) and novel (delta, epsilon, eta, theta) protein kinase C (PKC) isozymes are main targets of tumor promoters, such as phorbol esters and indolactam-V ( ILV). We have recently found that 1-hexyl derivatives of indolinelactam-V ( 2, 3), in which the indole ring of ILV was replaced with the indoline ring, showed a binding preference for novel PKCs over conventional PKCs. To develop a new ILV analogue displaying increased synthetic accessibility and improved binding selectivity for novel PKCs, we have designed 8-octyl-benzolactam-V9 ( 4), a simple analogue without the pyrrolidine moiety of 2 and 3. Compound 4 showed significant binding selectivity for isolated C1B domains of novel PKCs. Moreover, 4 translocated PKC epsilon and eta from the cytoplasm to the plasma membrane of HeLa cells at 1 mu M, whereas other PKC isozymes did not respond even at 10 mu M. These results indicate that 4 could be a selective activator for PKC epsilon and eta.