Methyl 2,3-bis(hexadecanoylamino)propanoate | 192223-81-7

• 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: Methyl 2,3-bis(hexadecanoylamino)propanoate
• CAS: 192223-81-7
• 化学式: C₃₆H₇₀N₂O₄
• 分子量: 594.963
• InChiKey: QFDBTUZEUNXMST-UHFFFAOYSA-N

物化性质

• 沸点：
  720.3±50.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  42
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2,3-bis(hexadecanoylamino)propanoate 在 4-二甲氨基吡啶 、 锂硼氢 、 异丙烯基氯甲酸酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2,3-Bis(palmitoylamino)-(O)-{(S)-N-tert-butoxycarbonyl-4-[bis(2-chloroethyl)amino]phenylalanyl}propan-1-ol
  参考文献：
  名称：

  The synthesis of novel melphalan derivatives as potential antineoplastic agents

  摘要：

  Five derivatives of melphalan ((S)-4- [bis(2-chloroethyl)amino]phenylalanine), an alkylating agent presently employed as an antineoplastic in humans, were designed and synthesised as potential prodrugs. Their antitumour activity was tested against P388 leukaemia in mouse after acute intraperitoneal or oral administration and compared with that of the parent compound.

  DOI：

  10.1016/s0223-5234(97)89087-3
• 作为产物：
  描述：

  methyl 2,3-diaminopropanoate p-toluenesulfonate 、 棕榈酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到Methyl 2,3-bis(hexadecanoylamino)propanoate
  参考文献：
  名称：

  Synthesis of Metal-Chelating Lipids to Sensitize Lanthanide Ions

  摘要：

  Sensitization of lanthanide ions is important for lanthanide ion-based assays and sensing. To the best of our knowledge, there are very few reports of lanthanide ion sensitization after it is incorporated into the liposome surface. This paper describes the syntheses of several saturated and polymerizable metal-chelating lipids based on chelidamic acid. The lipids are synthesized either from (S)-ornithine or racemic 2,3-diaminopropanoic acid. These lipids as well as polymerized liposomes incorporating these lipids sensitize lanthanide ions. Liposomes from the lipid 18-Eu3+ provided a probe that relies not only on the emission wavelengths of Eu3+ but also on a reproducible lifetime that can be used for protein identification.

  DOI：

  10.1021/jo026833k

文献信息

• Temperature- and Pressure-Induced Bilayer Phase Transitions of an Amide-Linked Phosphatidylcholine: A Contrasting Effect of Chain-Linkage Type
  作者：Toshiki Nakao、Masaki Goto、Masashi Kurashina、Nobutake Tamai、Mikito Yasuzawa、Hitoshi Matsuki

  DOI：10.1246/bcsj.20210395

  日期：2022.2.15

  temperature–pressure phase diagram and thermodynamic quantities of the phase transitions of the DPADPC bilayer membrane were compared with those of bilayer membranes of hydrophobic chain-linkage isomers, ester-liked dipalmitoylphosphatidylcholine (DPPC) and ether-linked dihexadecylphosphatidylcholine (DHPC). The thermodynamic quantities of the main transition for these PC bilayer membranes were similar to

  合成了具有两个酰胺键的非天然磷脂二棕榈酰氨基脱氧磷脂酰胆碱 (DPADPC)，并通过大气压下的差示扫描量热法和高压下的透光率测量观察了其双层相变。DPADPC 双层膜显示出不同的相变，这取决于大气压下脂质样品的热历史。在高压下也观察到与热历史相关的转变。将 DPADPC 双层膜的相变的温度-压力相图和热力学量与疏水链键异构体、酯状二棕榈酰磷脂酰胆碱 (DPPC) 和醚连接的二十六烷基磷脂酰胆碱 (DHPC) 的双层膜进行了比较。这些 PC 双层膜的主要转变的热力学量彼此相似，而 DPADPC 双层膜观察到交叉指型的抑制和水合晶相的高度稳定性。此外，核磁共振测量结果表明，DPADPC 双层膜凝胶相和液晶相中 PC 分子的运动性远低于 DPPC 和 DHPC 双层膜。根据上述结果，我们得出结论，PC 双层膜中的分子相互作用按醚键、酯键和酰胺键异构体的顺序增加。而对于 DPADPC 双层膜，观察
• Synthesis, in vitro transfection activity and physicochemical characterization of novel N,N′-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) amphiphilic derivatives
  作者：Ahmad Aljaberi、Pensung Chen、Michalakis Savva

  DOI：10.1016/j.chemphyslip.2004.09.017

  日期：2005.2

  A novel series of NN'-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) cationic derivatives was synthesized and screened for in vitro transfection activity at different charge ratios in the presence and absence of the helper lipids DOPE and cholesterol. Physicochemical properties of lipid-DNA complexes were studied by gel electrophoresis, fluorescence spectroscopy and dynamic light scattering. The interfacial properties of the lipids in isolation were studied using the Langmuir film balance technique at 23 degreesC. It was found that only lipoplexes formulated with the dioleoyl derivative, 1,21mt[5], mediated significant in vitro transfection activity. Optimum activity was obtained with 1,21mt[5]/DOPE mixture at a +/-charge ratio of 2. In agreement with the transfection results, 1,21mt[5] was the only lipid found to complex and retard DNA migration as verified by gel electrophoresis. Despite the efficient complexation, no significant condensation of plasmid DNA was observed as indicated by fluorescence spectroscopy measurements. Monolayer studies showed that the dioleoyl derivative 1,21mt[5] was the only lipid that existed in an all liquid-expanded state with a collapse area and collapse pressure of 59.5 Angstrom(2) and 38.7 mN/m, respectively. This lipid was also found to have the highest elasticity with a compressibility modulus at monolayer collapse of 80.4 mN/m. In conclusion, increased acyl chain fluidity and high molecular elasticity of cationic lipids were found to correlate with improved transfection activity. (C) 2004 Elsevier Ireland Ltd. All rights reserved.
• The synthesis of novel melphalan derivatives as potential antineoplastic agents
  作者：A.D. Morris、G Atassi、N Guilbaud、A.A. Cordi

  DOI：10.1016/s0223-5234(97)89087-3

  日期：1997.1

  Five derivatives of melphalan ((S)-4- [bis(2-chloroethyl)amino]phenylalanine), an alkylating agent presently employed as an antineoplastic in humans, were designed and synthesised as potential prodrugs. Their antitumour activity was tested against P388 leukaemia in mouse after acute intraperitoneal or oral administration and compared with that of the parent compound.
• Synthesis of Metal-Chelating Lipids to Sensitize Lanthanide Ions
  作者：Bidhan C. Roy、Marina Santos、Sanku Mallik、Andres D. Campiglia

  DOI：10.1021/jo026833k

  日期：2003.5.1

  Sensitization of lanthanide ions is important for lanthanide ion-based assays and sensing. To the best of our knowledge, there are very few reports of lanthanide ion sensitization after it is incorporated into the liposome surface. This paper describes the syntheses of several saturated and polymerizable metal-chelating lipids based on chelidamic acid. The lipids are synthesized either from (S)-ornithine or racemic 2,3-diaminopropanoic acid. These lipids as well as polymerized liposomes incorporating these lipids sensitize lanthanide ions. Liposomes from the lipid 18-Eu3+ provided a probe that relies not only on the emission wavelengths of Eu3+ but also on a reproducible lifetime that can be used for protein identification.