methanesulfonic acid 2-(2-(2-(4-(4-(tert-butoxycarbonylmethylamino)phenylethynyl)phenoxy)ethoxy)ethoxy)ethyl ester | 937701-51-4

• 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: methanesulfonic acid 2-(2-(2-(4-(4-(tert-butoxycarbonylmethylamino)phenylethynyl)phenoxy)ethoxy)ethoxy)ethyl ester
• 英文别名: 2-[2-[2-[4-[2-[4-[Methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]phenyl]ethynyl]phenoxy]ethoxy]ethoxy]ethyl methanesulfonate
• CAS: 937701-51-4
• 化学式: C₂₇H₃₅NO₈S
• 分子量: 533.643
• InChiKey: KNBMRRYMVTXCMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 2-(2-(2-(4-(4-(tert-butoxycarbonylmethylamino)phenylethynyl)phenoxy)ethoxy)ethoxy)ethyl ester 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.07h， 生成
  参考文献：
  名称：

  New Diphenylacetylenes as Probes for Positron Emission Tomographic Imaging of Amyloid Plaques

  摘要：

  A series of F-18 fluoropegylated diphenylacetylenes as probes for binding to A beta plaques were successfully prepared. These relatively rigid acetylenes, 12a, 12b, 14a, and 14b, displayed high binding affinities in postmortem AD brain homogenates (K-i ranging from 1.2 to 2.9 nM). In vivo biodistribution in normal mice exhibited excellent initial brain penetrations (4.42, 4.55, 5.41, and 6.78% dose/g at 2 min for [F-18]12a, 12b, 14a, and 14b, respectively). [F-18]12b and [F-18]14b, with a longer fluoropegylated unit, that is, n = 3, showed faster brain washout at 30 min postinjection (0.42 and 1.57% dose/g) as compared to the shorter fluoropegylated chain ligands, that is, [F-18]12a and [F-18]14a(1.03 and 3.69% dose/g). Autoradiography and homogenate binding confirmed the high binding signal due to A beta plaques. These preliminary results suggest that the novel diphenylacetylenes may be potentially useful for imaging of A beta plaques in the brain of patients with Alzheimer's disease.

  DOI：

  10.1021/jm070090j
• 作为产物：
  描述：

  4-(4-(2-(2-(2-(tert-butyldimethylsilanyloxy)ethoxy)ethoxy)ethoxy)phenylethynyl)phenylamine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 methanesulfonic acid 2-(2-(2-(4-(4-(tert-butoxycarbonylmethylamino)phenylethynyl)phenoxy)ethoxy)ethoxy)ethyl ester
  参考文献：
  名称：

  New Diphenylacetylenes as Probes for Positron Emission Tomographic Imaging of Amyloid Plaques

  摘要：

  A series of F-18 fluoropegylated diphenylacetylenes as probes for binding to A beta plaques were successfully prepared. These relatively rigid acetylenes, 12a, 12b, 14a, and 14b, displayed high binding affinities in postmortem AD brain homogenates (K-i ranging from 1.2 to 2.9 nM). In vivo biodistribution in normal mice exhibited excellent initial brain penetrations (4.42, 4.55, 5.41, and 6.78% dose/g at 2 min for [F-18]12a, 12b, 14a, and 14b, respectively). [F-18]12b and [F-18]14b, with a longer fluoropegylated unit, that is, n = 3, showed faster brain washout at 30 min postinjection (0.42 and 1.57% dose/g) as compared to the shorter fluoropegylated chain ligands, that is, [F-18]12a and [F-18]14a(1.03 and 3.69% dose/g). Autoradiography and homogenate binding confirmed the high binding signal due to A beta plaques. These preliminary results suggest that the novel diphenylacetylenes may be potentially useful for imaging of A beta plaques in the brain of patients with Alzheimer's disease.

  DOI：

  10.1021/jm070090j

文献信息

• Acetylene Derivatives And Their Use For Binding And Imaging Amyloid Plaques
  申请人：Kung Hank F.

  公开号：US20080166299A1

  公开（公告）日：2008-07-10

  The invention relates to radiolabeled compounds and their use in methods of imaging amyloid deposits, as well as to methods of their manufacture. The invention also relates to compounds for inhibiting the aggregation of amyloid proteins that form amyloid deposits, methods for delivering therapeutic agents to amyloid deposits, as well as methods of making compounds that inhibit the aggregation of amyloid proteins.

  这项发明涉及放射标记化合物及其在成像淀粉样沉积方法中的应用，以及它们的制造方法。该发明还涉及用于抑制形成淀粉样沉积的淀粉蛋白聚集的化合物，将治疗剂传递至淀粉样沉积的方法，以及制造抑制淀粉蛋白聚集的化合物的方法。