2-(2-(2-(4-(4-(4-(dimethylamino)phenyl)-1H-1,2,3-triazol-1-yl)phenoxy)ethoxy)ethoxy)ethanol | 946052-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-(2-(4-(4-(4-(dimethylamino)phenyl)-1H-1,2,3-triazol-1-yl)phenoxy)ethoxy)ethoxy)ethanol
• 英文别名: 2-[2-[2-[4-[4-[4-(Dimethylamino)phenyl]triazol-1-yl]phenoxy]ethoxy]ethoxy]ethanol
• CAS: 946052-62-6
• 化学式: C₂₂H₂₈N₄O₄
• 分子量: 412.489
• InChiKey: RHSZYIDPTHMWBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-(2-(4-(4-(4-(dimethylamino)phenyl)-1H-1,2,3-triazol-1-yl)phenoxy)ethoxy)ethoxy)ethanol 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以21%的产率得到4-(1-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)-1H-1,2,3-triazol-4-yl)-N,N-dimethylbenzenamine
  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：

  2-氯乙氧基-2-乙氧基二乙醇 在 copper(II) sulfate 、 L-脯氨酸 、 sodium iodide sodium azide 、 sodium carbonate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 2-(2-(2-(4-(4-(4-(dimethylamino)phenyl)-1H-1,2,3-triazol-1-yl)phenoxy)ethoxy)ethoxy)ethanol
  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

• WO2008/131148
  申请人：——

  公开号：——

  公开（公告）日：——
• DIPHENYL-HETEROARYL DERIVATIVES AND THEIR USE FOR BINDING AND IMAGING AMYLOID PLAQUES
  申请人：Kung Hank F.

  公开号：US20110158907A1

  公开（公告）日：2011-06-30

  This invention relates to a method of imaging amyloid deposits and to diphenyl-heteroaryl compounds, and methods of making radiolabeled diphenyl-heteroaryl compounds useful in imaging amyloid deposits. This invention also relates to compounds, and methods of making compounds for inhibiting the aggregation of amyloid proteins to form amyloid deposits, and a method of delivering a therapeutic agent to amyloid deposits.
• [EN] DIPHENYL-HETEROARYL DERIVATIVES AND THEIR USE FOR BINDING AND IMAGING AMYLOID PLAQUES<br/>[FR] DÉRIVÉS DE DIPHÉNYL-HÉTÉROARYLE ET LEUR UTILISATION POUR LA LIAISON ET L'IMAGERIE DE PLAQUES AMYLOÏDES
  申请人：UNIV PENNSYLVANIA

  公开号：WO2008131148A1

  公开（公告）日：2008-10-30

  [EN] This invention relates to a method of imaging amyloid deposits and to diphenyl-heteroaryl compounds, and methods of making radiolabeled diphenyl-heteroaryl compounds useful in imaging amyloid deposits. This invention also relates to compounds, and methods of making compounds for inhibiting the aggregation of amyloid proteins to form amyloid deposits, and a method of delivering a therapeutic agent to amyloid deposits.
  [FR] L'invention concerne un procédé d'imagerie de dépôts amyloïdes et des composés diphényl-hétéroaryle et des procédés de fabrication de composés diphényl-hétéroaryle radiomarqués utiles dans l'imagerie de dépôts amyloïdes. La présente invention concerne également des composés et des procédés de fabrication de composés pour inhiber l'agrégation de protéines amyloïdes pour former des dépôts amyloïdes et un procédé de distribution d'un agent thérapeutique aux dépôts amyloïdes.