2-[2-[2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]乙氧基]乙氧基]乙醇,甲磺酸 | 109789-40-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 2-[2-[2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]乙氧基]乙氧基]乙醇,甲磺酸
• 英文名称: 3,6,9,12,15-pentaoxaheptadecane-1,17-diyl dimethanesulfonate
• 英文别名: methanesulfonic acid 2-[2-(2-{2-[2-(2-methanesulfonyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl ester；hexaethylene glycol bis(methanesulfonate)；hexaethylene glycol bismesylate；hexaethylene glycol dimesylate；hexaethylene glycol mesylate；hexaethylene glycol dimethanesulfonate；Ms-PEG6-Ms；2-[2-[2-[2-[2-(2-methylsulfonyloxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethyl methanesulfonate
• CAS: 109789-40-4
• 化学式: C₁₄H₃₀O₁₁S₂
• 分子量: 438.518
• InChiKey: JOECUAAPEWVDEO-UHFFFAOYSA-N

物化性质

• 沸点：
  587.2±50.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  27
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  11

安全信息

• 储存条件：
  存储条件：2-8°C，需密封并保持干燥。

制备方法与用途

Ms-PEG6-Ms 是一种PROTAC连接子，属于PEG类化合物，可用于合成PROTAC分子。

反应信息

• 作为反应物：
  描述：

  2-[2-[2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]乙氧基]乙氧基]乙醇,甲磺酸 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 1,17-diiodo-3,6,9,12,15-pentaoxaheptadecane
  参考文献：
  名称：

  Design, synthesis and biological evaluation of estradiol-PEG-linked platinum(II) hybrid molecules: Comparative molecular modeling study of three distinct families of hybrids

  摘要：

  The synthesis of a series of 17 beta-estradiol-platinum(II) hybrid molecules is reported. The hybrids are made of a PEG linking chain of various length and a 2-(2'-aminoethyl)pyridine ligand. They are prepared from estrone in only 5 chemical steps with an overall yield of 22%. The length of the PEG chain does not influence the solubility of the compounds as it remains relatively constant throughout the series. MTT assays showed that the derivative with the longest PEG chain showed the best activity against two human breast cancer cell lines (MCF-7 and MDA-MB-231). The novel PEG-hybrids are also compared in terms of activities with two other families of 17 beta-estradiol-platinum(II) hybrids that we reported in previous studies. Molecular modeling study performed on a representative member of each family of hybrids reveals distinct molecular interactions with the estrogen receptor alpha which further corroborates their notably contrasting cytocidal activities on breast cancer cell lines. This study also shows that lipophilicity and the orientation of the tether chain between the estrogenic portion and the platinum(II) core contribute markedly to the biological activity of the various families of hybrids. The most active hybrids are those possessing an alkyl tether chain at position 16 beta of the steroid nucleus. For example. derivative 3 (p = 6) is about 16 times more potent on MCF-7 breast cancer cells than the corresponding 16 alpha-PEG-hybrids (2b) made in this study. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.09.004
• 作为产物：
  描述：

  六甘醇 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以97%的产率得到2-[2-[2-[2-[2-(2-羟基乙氧基)乙氧基]乙氧基]乙氧基]乙氧基]乙醇,甲磺酸
  参考文献：
  名称：

  通过氢键辅助环聚合的聚丙烯酰胺假冠醚

  摘要：

  含有大链内环（15-24元）的聚丙烯酰胺假冠醚是通过氢键介导的含聚环氧乙烷间隔基的双丙烯酰胺的环聚合反应合成的（PEGnDAAm，环氧乙烷单元：n = 3–6）。单体在卤化溶剂中经历双丙烯酰胺单元的分子内氢键，以动态地相邻放置两个烯烃。结果，即使在相对较高的单体浓度（200 mM）下，双丙烯酰胺均一地允许受控的自由基环聚合，而在1,2-二氯乙烷中没有任何宏观的凝胶化，从而直接提供精密的环聚丙烯酰胺和相关的共聚物，具有很高的环化效率（84– 98％）。由于存在链内环式悬垂物，环聚丙烯酰胺的玻璃化转变温度高于相应的带线性悬垂物的聚丙烯酰胺。©2016 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学 2016，54，3294-3302

  DOI：

  10.1002/pola.28218

文献信息

• Synthesis of peptide homo‐ and heterodimers as potential mimics of platelet‐derived growth factor BB
  作者：Louise A. Stubbing、Harveen Kaur、Sheryl X. Feng、Miranda Aalderink、Michael Dragunow、Margaret A. Brimble

  DOI：10.1002/pep2.24150

  日期：2020.7

  disease. The platelet‐derived growth factor receptor β (PDGFRβ)/platelet‐derived growth factor BB (PDGF‐BB) signalling pathway is key to the regulation of pericyte survival and proliferation. A series of peptide dimers mimicking the ligand PDGF‐BB were prepared in the hope of stimulating PDGFRβ internalisation and activation of this pathway. Copper‐catalysed azide‐alkyne cycloaddition of peptide monomers

  在诸如阿尔茨海默氏病等神经系统疾病中，周细胞的丢失与血脑屏障的泄漏有关。血小板衍生的生长因子受体（PDGFRβ）/血小板衍生的生长因子BB（PDGF-BB）信号通路是调节周细胞存活和增殖的关键。制备了一系列模拟配体PDGF-BB的肽二聚体，以期刺激PDGFRβ的内在化和该途径的激活。铜催化的叠氮基-炔烃环化肽单体与不同长度的PEG化接头的加成反应提供了所需的肽二聚体。在人脑周细胞测定中对肽二聚体的评估显示，浓度小于10μM时，对PDGFRβ的内在化和细胞增殖均无影响。浓度<10μM时，肽二聚体也不能作为PDGFRβ的拮抗剂。
• Design and Synthesis of Sn-Porphyrin Based Molecular Gates
  作者：Aurélie Guenet、Ernest Graf、Nathalie Kyritsakas、Mir Wais Hosseini

  DOI：10.1021/ic902265e

  日期：2010.2.15

  The design, synthesis, and structural characterization, both in solution by 1H NMR and in the solid state by X-ray diffraction on single crystals, of a series of molecular gates based on Sn-porphyrin derivatives are presented. The molecular system is based on a porphyrin core bearing at the meso positions either phenyl or pyridyl groups as a stator, octahedral Sn(IV) cation located at the center of

  提出了一系列基于锡卟啉衍生物的分子门的设计，合成和结构表征，无论是通过1 H NMR在溶液中还是在固体中通过X射线衍射在单晶上。分子系统是基于在卟啉芯轴承内消旋位置任一苯基或吡啶基作为定子，八面体的Sn（IV）阳离子位于卟啉作为铰链的中心，和不同的手柄至Sn-连接到卟啉O轴向键。还报道了在不同酸存在下复合物的稳定性。
• Synthesis of unique 17β-estradiol homo-dimers, estrogen receptors binding affinity evaluation and cytocidal activity on breast, intestinal and skin cancer cell lines
  作者：Gervais Bérubé、Daniel Rabouin、Valérie Perron、Blaise N’Zemba、René-C. Gaudreault、Sophie Parent、Éric Asselin

  DOI：10.1016/j.steroids.2006.06.007

  日期：2006.10

  A rapid and efficient synthesis of a series of C2-symmetric 17beta-estradiol homo-dimers is described. The new molecules are linked at position 17alpha of the steroid nucleus with either an alkyl chain or a polyethylene glycol chain. They are made from estrone in only five chemical steps with an overall yield exceeding 30%. The biological activity of these compounds was evaluated in vitro on estrogen

  描述了一系列C2对称的17β-雌二醇同型二聚体的快速有效合成。新分子在类固醇核的17α位与烷基链或聚乙二醇链连接。它们仅用五个化学步骤由雌酮制成，总收率超过30％。在体外对雌激素依赖性和非依赖性（ER +和ER-）人乳腺肿瘤细胞系MCF-7和MDA-MB-231评估了这些化合物的生物学活性。一些二聚体表现出针对ER +细胞系的选择性细胞毒活性。但是，与抗雌激素他莫昔芬相比，它们的细胞毒性不是很高。不幸的是，它们对雌激素受体α（ERalpha）仅显示弱亲和力，而对雌激素受体β（ERbeta）没有亲和力。还对人肠道（HT-29）和鼠皮肤癌（B16-F10）细胞系测试了这些新化合物，以进行进一步的生物学评估。有趣的是，发现二聚体对鼠类皮肤癌细胞系具有细胞毒性，但对肠道癌细胞系无活性。
• LOW MOLECULAR WEIGHT POLYETHYLENE GLYCOL DRUG CONJUGATES HAVING IMPROVED DRUG BIOLOGICAL ACTIVITY
  申请人：JENKEM TECHNOLOGY CO.,LTD.(TIANJIN)

  公开号：US20160082117A1

  公开（公告）日：2016-03-24

  Provided are polyethylene glycol drug conjugates of general formula (I), (II) or (III) and pharmaceutical compositions and a use thereof. The conjugates are formed by combining low molecular weight polyethylene glycol with 2-4 drug molecules. The conjugates can interact with receptor dimers or polymers, thereby improving the in vivo distribution of the drug, changing the oil and water distribution coefficient, enhancing the pharmacological activity, reducing the blood-brain barrier permeability of the drug, and improving the bioavailability of the drug.

  提供了一般式（I）、（II）或（III）的聚乙二醇药物共轭物，以及其药物组合物和用途。这些共轭物是通过将低分子量聚乙二醇与2-4个药物分子结合而形成的。这些共轭物可以与受体二聚体或聚合物相互作用，从而改善药物在体内的分布，改变油水分配系数，增强药理活性，降低药物的血脑屏障渗透性，并提高药物的生物利用度。
• Amino-polystyrene supported hexaethylene glycol-bridged ionic liquid as an efficient heterogeneous catalyst for water-mediated nucleophilic hydroxylation
  作者：Mudumala Veeranarayana Reddy、Seok Min Kang、Suah Yoo、Sang Sik Woo、Dong Wook Kim

  DOI：10.1039/c9ra00590k

  日期：——

  amino-polystyrene supported hexaethylene glycol-bridged ionic liquid (APS-HEGBIL) based on the copolymerization of amino-styrene with 1-vinyl imidazolium ionic liquid bearing hexaethylene glycol moieties, and its characterization by several analytical techniques. The resulting APS-HEGBIL catalyst was found to be remarkably efficient at catalyzing the selective nucleophilic hydroxylation of alkyl halides to produce

  我们报告了一种基于氨基苯乙烯与带有六甘醇部分的 1-乙烯基咪唑离子液体的共聚制备氨基聚苯乙烯负载的六甘醇桥接离子液体 (APS-HEGBIL) 的简单且环保的方法及其表征通过几种分析技术。发现所得的 APS-HEGBIL 催化剂在催化卤代烷的选择性亲核羟基化以在水中产生相应的醇方面非常有效，该醇充当溶剂和亲核氢氧化物源。该催化剂在十次循环后易于回收并保持其催化活性和稳定性，并具有优异的收率。该催化剂的主要特性是它在反应过程中显着提高了水的亲核性，并促进了极性和碱敏感的卤代烷反应物以优异的收率快速转化为醇。离子液体和聚合物材料的结合提供了准均相催化剂，这些催化剂通过简单的过滤回收，并为进行催化过程提供了环境友好的手段。