1,2-dipalmitoylamidopropan-3-ol | 163333-56-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,2-dipalmitoylamidopropan-3-ol
• 英文别名: 2,3-bis(palmitoylamino)propan-1-ol；N-[2-(hexadecanoylamino)-3-hydroxypropyl]hexadecanamide
• CAS: 163333-56-0
• 化学式: C₃₅H₇₀N₂O₃
• 分子量: 566.952
• InChiKey: MJJTYOOZXBJKLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  40
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-dipalmitoylamidopropan-3-ol 在 吡啶 作用下， 以 氯仿 为溶剂， 生成 N,N-dipalmitoyl-1,2-diaminopropyl-3-carbamoyl-(N,N-dimethylaminoethane)
  参考文献：
  名称：

  Synthesis, in vitro transfection activity and physicochemical characterization of novel N,N′-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) amphiphilic derivatives

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2004.09.017
• 作为产物：
  描述：

  2,3-diamino-1-tetrahydropyran-2-yloxypropane 在 吡啶 、 水 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 1,2-dipalmitoylamidopropan-3-ol
  参考文献：
  名称：

  Jia, Chunhua; Haines, Alan H., Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2521 - 2524

  摘要：

  DOI：

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
• p-[Bis(2-chloroethyl)amino]phenylalanine compounds
  申请人：Adir et Compagnie

  公开号：US05424464A1

  公开（公告）日：1995-06-13

  Antileukemic compounds of formula (I): ##STR1## in which: R.sup.1 represents hydrogen, linear or branched (C.sub.1 -C.sub.6)-alkoxycarbonyl or substituted or unsubstituted phenylalkoxycarbonyl, R.sup.2 represents any one of the following groups: ##STR2## in which: R.sub.3 or R.sub.4, which are identical or different, represent linear or branched (C.sub.6 -C.sub.19)-alkyl or linear or branched (C.sub.6 -C.sub.19)-alkenyl, and antileukemic products containing the same.

  化合物(I)的抗白血病化合物：##STR1## 其中：R.sup.1代表氢、线性或支链(C.sub.1-C.sub.6)-烷氧羰基或取代或未取代的苯基烷氧羰基，R.sup.2代表以下任何一种基团之一：##STR2## 其中：R.sub.3或R.sub.4，它们相同或不同，代表线性或支链(C.sub.6-C.sub.19)-烷基或线性或支链(C.sub.6-C.sub.19)-烯基，以及含有相同化合物的抗白血病产品。
• Nouveaux dérivés de p-[di(2-chloroéthyl)amino]phénylalanine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0604301A1

  公开（公告）日：1994-06-29

  Composé de formule (I) : dans laquelle : R₁représente un atome d'hydrogène, un radical alkoxycarbonyl (C₁-C₆) linéaire ou ramifié, ou phénylalkoxycarbonyl substitué ou non, R₂représente l'un quelconque des groupements suivants : dans lesquels : R₃ ou R₄,identiques ou différents, représentent un radical alkyle (C₆-C₁₉) linéaire ou ramifié ou alkényle (C₆-C₁₉) linéaire ou ramifié. Médicaments.

  式 (I) 的化合物： 其中 ： R₁ 代表氢原子、直链或支链烷氧基羰基（C₁-C₆）或取代或未取代的苯基烷氧基羰基、 R₂ 代表以下任何一个基团： 其中 ： R₃ 或 R₄（可以相同或不同）代表直链或支链烷基（C₆-C₁₉）或烯基（C₆-C₁₉）。 药用产品。
• 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.
• US5424464A
  申请人：——

  公开号：US5424464A

  公开（公告）日：1995-06-13