2-[2-(4-苯基甲氧基苯氧基)乙氧基]乙醇 | 142879-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-[2-(4-苯基甲氧基苯氧基)乙氧基]乙醇
• 英文名称: 2-(2-(4-(benzyloxy)phenoxy)ethoxy)ethanol
• 英文别名: Ethanol, 2-[2-[4-(phenylmethoxy)phenoxy]ethoxy]-；2-[2-(4-phenylmethoxyphenoxy)ethoxy]ethanol
• CAS: 142879-00-3
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: YXOCGOSUHMJYOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(4-苯基甲氧基苯氧基)乙氧基]乙醇 在 palladium on activated charcoal 氢气 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 1,4-bis<2-<2-<2-<2-<<2-<2-<2-<2-(4-benzyloxyphenoxy)ethoxy>ethoxy>ethoxy>ethoxy>phenoxy>ethoxy>ethoxy>ethoxy>ethoxy>benzene
  参考文献：
  名称：

  Amabilino, David B.; Anelli, Pier-Lucio; Ashton, Peter R., Journal of the American Chemical Society, 1995, vol. 117, # 45, p. 11142 - 11170

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苄氧基苯酚 、 2-氯乙氧基乙醇 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64 %的产率得到2-[2-(4-苯基甲氧基苯氧基)乙氧基]乙醇
  参考文献：
  名称：

  乙二醇苯基氨基乙基醚衍生物作为FOXM1抑制剂的合成及其抗肿瘤活性

  摘要：

  FOXM1 信号通路在多种人类癌症中高表达。基于FOXM1 DNA结合域的晶体结构，我们初步研究发现乙二醇（4-苄氧基苯基）环戊基氨基乙基醚XST20，可以抑制卵巢癌细胞增殖，对截短蛋白FOXM1表现出中等亲和力。本研究旨在开发一种具有更强亲和力和更高效率的 FOXM1 抑制剂，以用作分子工具和候选药物。我们通过分子对接评估优化方向并对XST20的结构进行系统改造. 合成了一类新的乙二醇苯基氨基乙基醚衍生物，评价了它们的抗癌活性和作用机制，总结了构效关系。化合物S2对FOXM1表现出更强的亲和力，提高了其活性，具有广谱抗癌作用。S2对 FOXM1 蛋白高表达水平的癌细胞显示出选择性抗增殖活性。S2应该是一种很好的化学生物学工具，也是未来研究靶向 FOXM1 的抗癌药物的潜在先导化合物。

  DOI：

  10.1016/j.ejmech.2022.114877

文献信息

• Silica-attached molecular receptor complexes for benzoates and naphthoates
  作者：Jozef A. Z. Hodyl、Stephen F. Lincoln、Kevin P. Wainwright

  DOI：10.1007/s10847-010-9782-8

  日期：2010.12

  A series of cyclen (1,4,7,10-tetraazacyclododecane) derived molecular receptors for aromatic oxoanions, that are activated by complexation with Cd(II), have been covalently linked to 3-(glycidoxy)propyl-functionalised silica gel (70–230 mesh). These immobilised receptor complexes are highly effective for the sequestration of o-hydroxybenzoates and 2-naphthoate from aqueous solution, achieving a >80% saturation level by stirring the material in the aqueous solution for 1 h at pH 7.00 and 298 K. Examination of the uptake levels of a variety of different benzoates and naphthoates suggests that the retention mechanism involves a combination of classical hydrogen bonding and non-classical, water mediated, O–H···π hydrogen bonding. Contrary to expectations, attachment of hydroxy terminated polyether chains to the periphery of the receptor complex diminished the level of uptake. Silica-attached receptor complexes of the type shown are effective materials for sequestering o-hydroxybenzoates from aqueous solution.

  一系列由环烯（1,4,7,10-四氮杂环十二烷）衍生的芳香族氧阴离子分子受体通过与镉（II）络合而被激活，并与 3-（缩水甘油）丙基功能化硅胶（70-230 目）共价连接。在 pH 值为 7.00 和 298 K 的条件下，将这种材料在水溶液中搅拌 1 h 就能达到 80% 的饱和度。对各种不同苯甲酸盐和萘酸盐吸收水平的研究表明，保留机制涉及经典氢键和以水为介质的非经典 O-H--π 氢键的组合。与预期相反，羟基末端聚醚链附着在受体复合物外围会降低吸收水平。所示类型的二氧化硅附着受体复合物是从水溶液中封存邻羟基苯甲酸盐的有效材料。
• FOXM1抑制剂及其制备方法和应用
  申请人：中国医学科学院医药生物技术研究所

  公开号：CN115304502A

  公开（公告）日：2022-11-08

  本发明涉及一种FOXM1抑制剂，其包括式I所示的化合物、其药用盐或酯、溶剂合物、异构体、多晶型物、同位素标记的化合物、代谢物或前药，并同时提供了其组合物、制备方法和应用，通过大量研究及筛选发现了上述系列化合物能够通过抑制FOXM1下调其下游靶蛋白的水平，从而发挥抗肿瘤活性，因此该系列化合物可用于预防和/或治疗肿瘤疾病。
• Preliminary evaluation of fluoro-pegylated benzyloxybenzenes for quantification of β-amyloid plaques by positron emission tomography
  作者：Yanping Yang、Hualong Fu、Mengchao Cui、Cheng Peng、Zhigang Liang、Jiapei Dai、Zhiyong Zhang、Chunping Lin、Boli Liu

  DOI：10.1016/j.ejmech.2015.09.028

  日期：2015.11

  A new series of fluoro-pegylated benzyloxybenzenes were designed, synthesized and evaluated as PET probes for early detection of A beta plaques. Molecular docking revealed that all of the flexible benzyloxybenzenes inserted themselves into the hydrophobic Va118_Phe20 cleft on the flat spine of the A beta fiber, in a manner similar to that of IMPY molecule. The most potent probe, [F-18]9a, exhibited a combination of high binding affinity to A beta aggregates (K-i= 21.0 +/- 4.9 nM), high initial brain uptake (9.14% ID/g at 2 min), fast clearance from normal brain tissue (1.79% ID/g at 60 min), and satisfactory in vivo biostability in the brain (95% of intact form at 2 min). [F-18]9a clearly labeled A beta plaques in in vitro autoradiography of postmortem AD patients and Tg mice brain sections. Ex vivo autoradiography further demonstrated that [F-18]9a did penetrate the intact BBB and specifically bind to A beta plaques in vivo. Overall, [F-18]9a may be a potential PET probe for imaging A beta plaques in AD brains. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Simple Mechanical Molecular and Supramolecular Machines: Photochemical and Electrochemical Control of Switching Processes
  作者：Peter R. Ashton、Roberto Ballardini、Vincenzo Balzani、Sue E. Boyd、Alberto Credi、Maria T. Gandolfi、Marcos Gómez-López、Sayeedha Iqbal、Douglas Philp、Jon A. Preece、Luca Prodi、Howard G. Ricketts、J. Fraser Stoddart、Malcolm S. Tolley、Margherita Venturi、Margherita Venturi、Andrew J. P. White、David J. Williams

  DOI：10.1002/chem.19970030123

  日期：1997.1

  AbstractPhotochemical control of a self‐assembled supramolecular 1:1 pseudorotaxane (formed between a tetracationic cyclophane, namely the tetrachloride salt of cyclobis(paraquat‐p‐phenylene), and 1,5‐bis[2‐(2‐(2‐hydroxy)ethoxy)ethoxy]naphthalene) has been achieved in aqueous solution. The photochemical one‐electron reduction of the cyclophane to the radical trication weakens the noncovalent bonding interactions between the cyclophane and the naphthalene guest—π‐π interactions between the π‐electron‐rich and π‐electron‐poor aromatic systems, and hydrogen‐bonding interactions between the acidic α‐bipyridinium hydrogen atoms of the cyclophane and the polyether oxygen atoms of the naphthalene derivative—sufficiently to allow the guest to dethread from the cavity; the process can be monitored by the appearance of naphthalene fluorescence. The radical tricationic cyclophane can be oxidized back to the tetracation in the dark by allowing oxygen gas into the system. This reversible process is marked by the disappearance of naphthalene fluorescence as the molecule is recomplexed by the tetracationic cyclophane. This supramolecular system can be chemically modified such that the π‐electron‐rich unit, either a naphthalene derivative or a hydroquinone ring, and the tetracationic cyclophane are covalently linked. We have demonstrated that the π‐electron‐rich residue in this system is totally “self‐complexed” by the cyclophane to which it is covalently attached. Additionally, the self‐complexation can be switched “off” and “on” by electrochemical two‐electron reductions and oxidations, respectively, of the tetracationic cyclophane component. Thus, we have achieved the construction of two switches at the nanoscale level, one driven by photons and the other by electrons.