2-Acetoxy-stearinsaeure | 71271-23-3

• 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: 2-Acetoxy-stearinsaeure
• 英文别名: 2-Acetoxyoctadecanoic acid；2-acetyloxyoctadecanoic acid
• CAS: 71271-23-3
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: VHVMZXQGJMKAIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Acetoxy-stearinsaeure 在 氯化亚砜 作用下， 以 乙醚 为溶剂， 生成 3-Acetoxy-1-diazo-2-nonadecanon
  参考文献：
  名称：

  Stereospecific Syntheses of Long-Chain 1,2,3,4-Alkanetetrols

  摘要：

  DOI：

  10.1021/jo01028a011
• 作为产物：
  描述：

  2-溴代十八酸 在 吡啶 作用下， 生成 2-Acetoxy-stearinsaeure
  参考文献：
  名称：

  Stereospecific Syntheses of Long-Chain 1,2,3,4-Alkanetetrols

  摘要：

  DOI：

  10.1021/jo01028a011

文献信息

• Zinc(II)-facilitated hydrolysis of 2-hydroxyacid esters. A model for carboxypeptidase A
  作者：Rodney F. Boyer

  DOI：10.1016/0022-1902(80)80069-8

  日期：1980.1

  Zn(II) complexes of naturally-occurring 2-hydroxyacids have been prepared by two separate methods: (1) Reaction between 2-hydroxyacid and Zn(II); and (2) Zn(II)-facilitated hydrolysis of esters of 2-hydroxyacids. For example, reaction of 0-acetyl 2-hydroxyoctadecanoic acid with Zn(II) in warm 95% ethanol led to formation of Zn(2-hydroxyoctadecanoate)2. This general reaction should provide insight into

  天然存在的2-羟基酸的Zn（II）配合物已通过两种单独的方法制备：（1）2-羟基酸与Zn（II）的反应；（2）Zn（II）促进的2-羟基酸的酯的水解。例如，在温暖的95％乙醇中0-乙酰基2-羟基十八碳烯酸与Zn（II）的反应导致形成Zn（2-羟基十八碳酸酯）2。该一般反应应提供洞察力，以羧肽酶催化的酯水解中离去基团的金属离子活化的重要性。
• Preparation of prodrugs for selective drug delivery
  申请人：Mills L. Randell

  公开号：US20050080260A1

  公开（公告）日：2005-04-14

  Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

  合成具有A-B-C化学式的化合物，可用于药物传递等应用，其中A是化学发光基团，B是光致变色基团，C是生物活性基团，其中A-B-C可作为前药。本发明的新型合成方法用于形成前药，包括以下步骤：(1)形成苯酮，(2)形成二芳基乙烯，(3)将邻苯二甲酰亚胺基团连接到乙烯的至少一个芳基上，形成邻苯二甲酰亚胺-乙烯共轭物，(4)缩合两个乙烯-邻苯二甲酰亚胺共轭物，形成邻苯二甲酰亚胺-戊二烯共轭物，(5)通过与肼反应将邻苯二甲酰亚胺转化为邻苯二酰肼，形成本发明的载体化合物，(6)将载体化合物与药物的亲核基团反应，形成相应的前药。另外，可以通过使用卤代二芳基乙烯制备相应的阳离子类似的类似类似染料化合物。然后，通过与亲核试剂反应保护阳离子类似化合物，并通过钯催化的胺化与氨基邻苯二甲酰亚胺偶联，形成保护的邻苯二甲酰亚胺-戊二烯共轭物。后者与肼回流，将其邻苯二甲酰亚胺转化为邻苯二酰肼，并酸化以得到载体。本发明的另一个方面涉及将这些化合物用作抗病毒剂，用于治疗病毒感染，如HIV，以及用作抗癌剂，用于治疗结肠癌、肺癌和乳腺癌等癌症。
• Quantitative Measurements of Recombinant HIV Surface Glycoprotein 120 Binding to Several Glycosphingolipids Expressed in Planar Supported Lipid Bilayers
  作者：John C. Conboy、Katherine D. McReynolds、Jacquelyn Gervay-Hague、S. Scott Saavedra

  DOI：10.1021/ja011225s

  日期：2002.2.1

  The interaction of recombinant HIV-1 surface glycoprotein gp120 (rgp120) with natural isolates of lactosylceramide (LacCer), glucosylceramide (GlcCer), and galactosylceramide (GaiCer) has been quantitatively measured under equilibrium conditions using total internal reflection fluorescence (TIRF) spectroscopy. The binding affinity (K-a) of rgp120 to these glycosphingolipids (GSLs), reconstituted at 5 mol % in supported planar lipid bilayers composed of 95 mol % POPC, is ca. 10(6) M-1 for dissolved rgp120 concentrations greater than 25 nM. In contrast, at concentrations of rgp120 between 0.2 and 15 nM, rgp120 does not bind significantly to LacCer and GlcCer, but has a high affinity for GalCer with a measured K-a value of 1.6 x 10(9) M-1. However, protein surface coverage measurements show that this strong binding process accounts for very little of the total protein adsorbed over the entire concentration range studied. At a protein concentration of ca. 20 nM, the surface coverage is only 3% of that achieved at apparent saturation (i.e., when the protein concentration is ca. 220 nM). Thus the "high affinity" binding sites comprise only a small fraction of the total number of binding sites. Several other variables were investigated, Rgp120 binding behavior at membranes doped with alpha-hydroxygalactosylceramide (alpha-GalCer) was very similar to that observed with GalCer, showing that the presence/absence of an alpha-hydroxy moiety does not significantly affect galactosylceramide recognition. Phase segregation of GalCer, which occurs when the mole fraction of this GSL in a POPC bilayer exceeds ca. 0.1, was also investigated and showed no effect on binding affinity at low rgp120 concentrations. To investigate the influence of fatty acid chain length, GSLs with monodisperse C-18 and C-24 chain lengths, both with and without an alpha-hydroxy moiety, were synthesized, and their binding affinity to rgp120 was examined. Relative to the natural isolates (which contain a mixture of chain lengths), minimal differences were observed; thus among the compounds tested, fatty acid chain length does not affect GSL recognition. The results of this work should aid efforts to design anti-HIV-1 agents based on membrane-tethered, carbohydrate-based receptors for rgp120.
• Guest, Journal of the American Chemical Society, 1947, vol. 69, p. 301
  作者：Guest

  DOI：——

  日期：——
• ANTIVIRAL AGENTS
  申请人：SYNTEK AB

  公开号：EP0207984A1

  公开（公告）日：1987-01-14