2-(2-(2-(4-iodophenoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate | 932711-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-(2-(4-iodophenoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate
• 英文别名: 2-[2-[2-(4-Iodophenoxy)ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 932711-47-2
• 化学式: C₁₉H₂₃IO₆S
• 分子量: 506.359
• InChiKey: JKEZXDRDCUQOGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-(2-(4-iodophenoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 在 copper(II) sulfate 、 L-脯氨酸 sodium azide 、 四丁基氟化铵 、 sodium carbonate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 24.5h， 生成 4-(1-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)-1H-1,2,3-triazol-4-yl)-N-methylbenzenamine
  参考文献：
  名称：

  Quick Assembly of 1,4-Diphenyltriazoles as Probes Targeting β-Amyloid Aggregates in Alzheimer's Disease

  摘要：

  Accumulation of beta-amyloid aggregates (A beta) in the brain is linked to the pathogenesis of Alzheimer's disease (AD). We report a novel approach for producing 1,4-diphenyltriazoles as probes for targeting A beta aggregates in the brain. The imaging probes, a series of substituted tricyclic 1,4-diphenyltriazoles showing excellent binding affinities to A beta aggregates (K-i = 4-30 nM), were conveniently assembled by "click chemistry." Two radioiodinated probes, [I-125]10a and [I-125]10b, and two radiofluorinated probes, [F-18]17a and [F-18]17b, exhibited moderate lipophilicities and showed excellent initial brain penetrations and fast washouts from the normal mouse brain. In vitro autoradiography of postmortem AD brain sections and homogenates showed that these triazoles were binding to A beta plaques. Preliminary results strongly suggest that use of click chemistry, which led to a 1,4-diphenyltriazole-based core, is a highly convenient and flexible approach for assembling novel imaging agents for targeting A beta aggregates in senile plaques in the living human brain.

  DOI：

  10.1021/jm070467l
• 作为产物：
  描述：

  4-碘苯酚 在 sodium iodide 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 2-(2-(2-(4-iodophenoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Quick Assembly of 1,4-Diphenyltriazoles as Probes Targeting β-Amyloid Aggregates in Alzheimer's Disease

  摘要：

  Accumulation of beta-amyloid aggregates (A beta) in the brain is linked to the pathogenesis of Alzheimer's disease (AD). We report a novel approach for producing 1,4-diphenyltriazoles as probes for targeting A beta aggregates in the brain. The imaging probes, a series of substituted tricyclic 1,4-diphenyltriazoles showing excellent binding affinities to A beta aggregates (K-i = 4-30 nM), were conveniently assembled by "click chemistry." Two radioiodinated probes, [I-125]10a and [I-125]10b, and two radiofluorinated probes, [F-18]17a and [F-18]17b, exhibited moderate lipophilicities and showed excellent initial brain penetrations and fast washouts from the normal mouse brain. In vitro autoradiography of postmortem AD brain sections and homogenates showed that these triazoles were binding to A beta plaques. Preliminary results strongly suggest that use of click chemistry, which led to a 1,4-diphenyltriazole-based core, is a highly convenient and flexible approach for assembling novel imaging agents for targeting A beta aggregates in senile plaques in the living human brain.

  DOI：

  10.1021/jm070467l

文献信息

• Host-guest complexation-triggered chiroptical change of poly(phenylacetylene)s bearing binaphthocrown ether moieties on the main chain
  作者：Ryosuke Sakai、Takafumi Yonekawa、Issei Otsuka、Ryohei Kakuchi、Toshifumi Satoh、Toyoji Kakuchi

  DOI：10.1002/pola.23881

  日期：2010.3.1

  cyclopolymerized with a rhodium catalyst to produce novel poly(phenylacetylene)s bearing a different cavity size of the chiral crown ether in the repeating units (2a–c). In the circular dichroism spectra of the resulting polymers, characteristic Cotton effects were observed in the range from 350 to 500 nm corresponding to the absorption of the conjugated polymer backbone, indicating that the polymers possessed a

  将具有各自氧乙烯链长度的二乙炔单体与铑催化剂进行环聚合，以生产在重复单元（2a – c）中带有不同手性冠醚空腔尺寸的新型聚苯乙炔。在所得聚合物的圆二色性光谱中，观察到特征性的棉花效应在350至500 nm范围内，与共轭聚合物主链的吸收相对应，表明该聚合物具有螺旋结构，并由其诱导了过量的单螺杆感。共价键联的联萘单元。2a – c的宿主-客体复合体非手性宾客根据主链构象的波动产生了手性改变。络合诱导的手性改变的行为基本上由双萘冠醚单元的腔尺寸决定。另外，在2a - c与手性客体络合的情况下，观察到手性响应的螺旋度发生变化，这也取决于冠醚的大小。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem 48：1197-1206，2010年
• Synthesis and evaluation of indolinyl- and indolylphenylacetylenes as PET imaging agents for β-amyloid plaques
  作者：Wenchao Qu、Seok-Rye Choi、Catherine Hou、Zhiping Zhuang、Shunichi Oya、Wei Zhang、Mei-Ping Kung、Rajesh Manchandra、Daniel M. Skovronsky、Hank F. Kung

  DOI：10.1016/j.bmcl.2008.07.077

  日期：2008.9

  Two new phenylacetylene derivatives, 5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)indoline 8 and 5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)-1H-indole 14, targeting beta-amyloid ( Ab) plaques have been prepared. In vitro binding carried out in tissue homogenates prepared from postmortem AD brains with [(125)[] IMPY (6-iodo-2-(40-dimethylamino-phenyl-imidazo[1,2-a]pyridine) as the radioligand indicated good binding affinities (K-i = 4.0 and 1.5 nM for 8 and 14, respectively). Brain penetration of the corresponding radiofluorinated ligands, evaluated in the normal mice, showed good initial brain penetration (4.50 and 2.43% ID/g (injected dose/gram) for [F-18]8 and [F-18]14 at 2 min after injection) with moderate to low washout rates from the brain (1.71% ID/g at 2h and 2.10% ID/g at 3 h, respectively). Autoradiography and homogenate binding studies demonstrated the high specific binding of [F-18]14 to the Ab plaques; however, [F-18]8 showed low specific binding. These preliminary results identified that indolylphenylacetylene, 14, may be a good lead for further structural modi. cation to develop a useful Ab plaque imaging agent. (C) 2008 Elsevier Ltd. All rights reserved.
• Conformationally Constrained Analogues of Diacylglycerol (DAG). 27. Modulation of Membrane Translocation of Protein Kinase C (PKC) Isozymes α and δ by Diacylglycerol Lactones (DAG-<scp>l</scp>actones) Containing Rigid-Rod Acyl Groups
  作者：Krishnan Malolanarasimhan、Noemi Kedei、Dina M. Sigano、James A. Kelley、Christopher C. Lai、Nancy E. Lewin、Robert J. Surawski、Vladimir A. Pavlyukovets、Susan H. Garfield、Stephen Wincovitch、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm061289j

  日期：2007.3.1

  Highly rigid and geometrically well-defined rods composed of ethynylene-substituted aromatic spacers [oligo(p-phenyleneethynylene), OPE] were incorporated as acyl moieties on diacylglycerol lactones (DAG-lactones) and investigated for their ability to bind to protein kinase C (PKC) and translocate PKC alpha and delta isoforms to plasma and internal membranes. The kinetics of PKC translocation were correlated with biological responses, viz. ERK phosphorylation, induction of IL-6 secretion, inhibition of cell proliferation, and induction of cellular attachment, that display very different time courses. Because OPE rods assemble through noncovalent forces and form stable films, they may influence the microdomain environment around the DAG-lactone membrane-binding site. A comparison of two DAG-lactones (1 and 10), one with two PE units (1) and the other with an equivalent flexible acyl chain (10) of matching lipophilicity, clearly demonstrated the effect of the rigid OPE chain in substantially prolonging the translocated state of both PKC alpha and delta.