Ethyl 2-(didodecylamino)acetate | 1026502-19-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 2-(didodecylamino)acetate
• CAS: 1026502-19-1
• 化学式: C₂₈H₅₇NO₂
• 分子量: 439.766
• InChiKey: LAVRYJGFCGJUGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  31
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(didodecylamino)acetate 在 乙醇 、 potassium hydroxide 作用下， 以65 %的产率得到N,N-di-n-dodecylglycine
  参考文献：
  名称：

  阳离子脂质共轭双亚芳基羟吲哚衍生物作为广谱乳腺癌选择性治疗剂

  摘要：

  乳腺癌是一种异质性恶性肿瘤，在治疗反应、总生存期等方面存在广泛差异。可用化学治疗剂实现临床成功的主要挑战是维持全身生物分布和避免非特异性不良反应。双亚芳基羟吲哚是具有中等效力的雌激素受体 (ER) 选择性生物活性分子。在这里，我们设计、合成和评估了一系列双脂肪链阳离子脂质共轭双亚芳基羟吲哚分子，这些分子具有不同的接头性质、碳间隔基长度和疏水双链。我们观察到，在各种结构类似物中，含有 C8 双链的分子PGC8、S2C8和S3C8在不同的癌细胞系中显示出有效的癌细胞选择性细胞毒性，IC 50范围为 4 至 7 µM。这些分子在 ER + 乳腺癌细胞而非非癌细胞中选择性地诱导细胞凋亡、ROS 产生和 G1/S 期细胞周期抑制。此外，这些分子形成了同质的自组装体，显示出具有正表面电荷的有效流体动力学直径。自组装还显示出突出的癌细胞选择性摄取和 DNA 结合能力。因此，我们已经证明成功地将地塞米松掺入自组装体中，并且即使在

  DOI：

  10.1016/j.bioorg.2023.106395
• 作为产物：
  描述：

  双十二烷基胺 、 溴乙酸乙酯 以 乙醇 为溶剂， 反应 8.0h， 生成 Ethyl 2-(didodecylamino)acetate
  参考文献：
  名称：

  Efficient and Highly Selective Copper(II) Transport across a Bulk Liquid Chloroform Membrane Mediated by Lipophilic Dipeptides

  摘要：

  Several structurally simple N-monoalkylated and -dialkylated dipeptides made of alpha-amino acids Gly, Phe, and Leu, 1-11, were synthesized and investigated as carriers for the transport of Cu(II), Zn(II), and Ni(II) from an aqueous pH = 5.6 buffer source to a 0.1 M HCl receiving phase across a bulk chloroform membrane. The proton-driven translocation was followed during the process by analyzing the metal ion concentrations in the three phases. The transport efficiency depends on the ease of formation of a neutral complex with Cu(II) (the peptide group and carboxylic acid being deprotonated) at the source-chloroform interface and on that of its disruption by protonation at the receiving phase: the carrier's Lipophilicity favors the metal ion uptake and not the release. By modulating the length of the N-alkyl chains and the hydrophobicity of the dipeptide moiety, a quite remarkable transport efficiency was observed for Cu(II), in most cases superior to that of the industrial extractant Kelex 100. Moreover, using L,L- and L,D-N-octyl-PheLeu as carriers, remarkable diastereomeric effects were observed in the rate of uptake and release of Cu(II) ion although the differences mutually compensate in the overall transport rate. Under the conditions used the carriers are much less effective in the translocation of Zn(II) and Ni(II) and their transport efficiency drops dramatically in the presence of Cu(II), the latter being favored by factors of 1.2 x 10(3) and > 10(4), respectively. Such very high selectivities depend on the fact that only Cu(II) among other transition metal ions Can form neutral complexes at the pH value of the source phase.

  DOI：

  10.1021/jo9703257

文献信息

• Efficient and Highly Selective Copper(II) Transport across a Bulk Liquid Chloroform Membrane Mediated by Lipophilic Dipeptides
  作者：Marco C. Cleij、Paolo Scrimin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1021/jo9703257

  日期：1997.8.1

  Several structurally simple N-monoalkylated and -dialkylated dipeptides made of alpha-amino acids Gly, Phe, and Leu, 1-11, were synthesized and investigated as carriers for the transport of Cu(II), Zn(II), and Ni(II) from an aqueous pH = 5.6 buffer source to a 0.1 M HCl receiving phase across a bulk chloroform membrane. The proton-driven translocation was followed during the process by analyzing the metal ion concentrations in the three phases. The transport efficiency depends on the ease of formation of a neutral complex with Cu(II) (the peptide group and carboxylic acid being deprotonated) at the source-chloroform interface and on that of its disruption by protonation at the receiving phase: the carrier's Lipophilicity favors the metal ion uptake and not the release. By modulating the length of the N-alkyl chains and the hydrophobicity of the dipeptide moiety, a quite remarkable transport efficiency was observed for Cu(II), in most cases superior to that of the industrial extractant Kelex 100. Moreover, using L,L- and L,D-N-octyl-PheLeu as carriers, remarkable diastereomeric effects were observed in the rate of uptake and release of Cu(II) ion although the differences mutually compensate in the overall transport rate. Under the conditions used the carriers are much less effective in the translocation of Zn(II) and Ni(II) and their transport efficiency drops dramatically in the presence of Cu(II), the latter being favored by factors of 1.2 x 10(3) and > 10(4), respectively. Such very high selectivities depend on the fact that only Cu(II) among other transition metal ions Can form neutral complexes at the pH value of the source phase.
• Cationic lipid-conjugated bis-arylidene oxindole derivatives as broad-spectrum breast cancer-selective therapeutics
  作者：Md Yousuf、Kathyayani Sridharan、Tanushree Mishra、Namita S. Mahadik、Rajkumar Banerjee、Susanta S. Adhikari

  DOI：10.1016/j.bioorg.2023.106395

  日期：2023.4

  available chemotherapeutic agents in achieving clinical success are in maintaining systemic bio-distribution and avoiding non-specific adverse effects. Bis-arylidene oxindoles are estrogen receptor (ER)-selective bioactive molecules with moderate potency. In here, we have designed, synthesized and evaluated a series of twin aliphatic chain cationic lipid-conjugated bis-arylidene oxindole molecules with variations

  乳腺癌是一种异质性恶性肿瘤，在治疗反应、总生存期等方面存在广泛差异。可用化学治疗剂实现临床成功的主要挑战是维持全身生物分布和避免非特异性不良反应。双亚芳基羟吲哚是具有中等效力的雌激素受体 (ER) 选择性生物活性分子。在这里，我们设计、合成和评估了一系列双脂肪链阳离子脂质共轭双亚芳基羟吲哚分子，这些分子具有不同的接头性质、碳间隔基长度和疏水双链。我们观察到，在各种结构类似物中，含有 C8 双链的分子PGC8、S2C8和S3C8在不同的癌细胞系中显示出有效的癌细胞选择性细胞毒性，IC 50范围为 4 至 7 µM。这些分子在 ER + 乳腺癌细胞而非非癌细胞中选择性地诱导细胞凋亡、ROS 产生和 G1/S 期细胞周期抑制。此外，这些分子形成了同质的自组装体，显示出具有正表面电荷的有效流体动力学直径。自组装还显示出突出的癌细胞选择性摄取和 DNA 结合能力。因此，我们已经证明成功地将地塞米松掺入自组装体中，并且即使在