1-fluoro-4-(4-iodobenzyloxy)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-fluoro-4-(4-iodobenzyloxy)benzene
• 英文别名: 1-Fluoro-4-[(4-iodophenyl)methoxy]benzene
• 化学式: C₁₃H₁₀FIO
• 分子量: 328.125
• InChiKey: WFCPHRHKQQOAFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氟苯酚 、 4-碘苄基溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以77.1%的产率得到1-fluoro-4-(4-iodobenzyloxy)benzene
  参考文献：
  名称：

  Radioiodinated Benzyloxybenzene Derivatives: A Class of Flexible Ligands Target to β-Amyloid Plaques in Alzheimer’s Brains

  摘要：

  Benzyloxybenzene, as a novel flexible scaffold without rigid planarity, was synthesized and evaluated as ligand toward A beta plaques. The binding site calculated for these flexible ligands was the hydrophobic Val18_Phe20 channel on the flat surface of A beta fiber. Structure activity relationship analysis generated a common trend that binding affinities declined significantly from para-substituted ligands to ortho-substituted ones, which was also quantitatively illustrated by 3D-QSAR modeling. Autoradiography in vitro further confirmed the high affinities of radioiodinated ligands [I-125]4, [I-125]24, and [I-125]22 (K-i = 24.3, 49.4, and 17.6 nM, respectively). In biodistribution, [I-125]4 exhibited high initial uptake and rapid washout property in the brain with brain(2 min)/brain(60 min) ratio of 16.3. The excellent in vitro and in vivo biostability of [I-125]4 enhanced its potential for clinical application in SPECT imaging of A beta plaques. This approach could also allow the design of a new generation of A beta targeting ligands without rigid and planar framework.

  DOI：

  10.1021/jm5004396

文献信息

• PHENYL BENZYL ETHER DERIVATIVE AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：ZHANG Zhiyong

  公开号：US20170037008A1

  公开（公告）日：2017-02-09

  Parts of compounds, after being labeled by radionuclide, of the phenyl benzyl ether derivative, are used as Aβ plaque imaging agent. The structural formula of the phenyl benzyl ether derivative is shown by formula (I). The present invention develops a kind of brand new phenyl benzyl ether derivative which has high affinity with Aβ plaques in brains of AD patients. The chemical structure of the phenyl benzyl ether derivative is different from that of compounds disclosed in the prior art and the phenyl benzyl ether derivative belongs to a brand new compound for diagnosing and treating AD. The obtained Aβ plaque imaging agent has the advantages that the in-vivo stability is good, the fat solubility is low, the removal speed for the brain is fast, the problem of removing the radionuclide in vivo does not exist, and the application prospect and the market value are great.

  化合物的部分，在被放射性核素标记后，苯基苄醚衍生物被用作Aβ斑块成像剂。苯基苄醚衍生物的结构式如公式（I）所示。本发明开发了一种全新的苯基苄醚衍生物，其与AD患者大脑中的Aβ斑块具有高亲和力。苯基苄醚衍生物的化学结构与先前公开的化合物不同，且该苯基苄醚衍生物属于一种全新的用于诊断和治疗AD的化合物。所得的Aβ斑块成像剂具有优点，即体内稳定性好，脂溶性低，对大脑的清除速度快，不存在体内去除放射性核素的问题，且应用前景和市场价值巨大。
• Aryl derivatives
  申请人：ZENECA LIMITED

  公开号：EP0488602A1

  公开（公告）日：1992-06-03

  The invention concerns an aryl derivative of the formula I, wherein Ar¹ is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X¹ is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X¹ is a group of the formula         -X⁴-CR₂- or -CR₂-X⁴- wherein X⁴ is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl; each of Ar² and Ar³ is optionally substituted phenylene; X² is oxy, thio, sulphinyl or sulphonyl; R¹ is (1-4C)alkyl; and R² and R³ together form a group of the formula -A¹-X³-A²- which together with the carbon atom to which A¹ and A² are attached define a ring having 5 to 7 ring atoms, wherein each of A¹ and A² is (1-3C)alkylene and X³ is oxy, thio, sulphinyl or sulphonyl; which compounds are inhibitors of 5-lipoxygenase and are useful in the treatment of inflammatory or allergic disease.

  本发明涉及一种式 I 的芳基衍生物、 其中 Ar¹ 是任选取代的苯基、萘基或杂环分子，X¹ 是氧、硫、亚硫酰基、磺酰基、二氟亚甲基、亚氨基、(1-4C)烷基亚氨基或任选取代的(1-4C)亚烷基，或 X¹ 是式中的基团 -X⁴-CR₂-或-CR₂-X⁴- 其中 X⁴ 是氧、硫、亚硫酰、磺酰或羰基，每个 R 是氢、甲基或乙基； Ar² 和 Ar³ 各为任选取代的亚苯基； X² 是氧基、硫代、亚砜基或磺酰基； R¹ 是 (1-4C) 烷基；以及 R² 和 R³ 共同形成一个式 -A¹-X³-A²- 的基团，该基团与 A¹ 和 A² 所连接的碳原子共同定义了一个具有 5 至 7 个环原子的环，其中 A¹ 和 A² 均为 (1-3C)亚烷基，X³ 为氧基、硫代、亚砜基或磺酰基； 这些化合物是 5-脂氧合酶的抑制剂，可用于治疗炎症或过敏性疾病。
• US5225438A
  申请人：——

  公开号：US5225438A

  公开（公告）日：1993-07-06
• US5272173A
  申请人：——

  公开号：US5272173A

  公开（公告）日：1993-12-21
• US5276037A
  申请人：——

  公开号：US5276037A

  公开（公告）日：1994-01-04