4-(formyl)-1-(2-(methoxymethoxy)ethyl)-1H-1,2,3-triazole | 1354569-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(formyl)-1-(2-(methoxymethoxy)ethyl)-1H-1,2,3-triazole
• 英文别名: 1-[2-(Methoxymethoxy)ethyl]triazole-4-carbaldehyde
• CAS: 1354569-79-1
• 化学式: C₇H₁₁N₃O₃
• 分子量: 185.183
• InChiKey: ZGIMYAQTFKCLTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(formyl)-1-(2-(methoxymethoxy)ethyl)-1H-1,2,3-triazole 、 二乙基(4-硝基苯甲基)磷酸盐 在 盐酸 、 tin(II) chloride dihdyrate 、 potassium tert-butylate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (E)-4-(4-aminostyryl)-1-(2-hydroxyethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and Evaluation of ¹⁸F-Labeled Styryltriazole and Resveratrol Derivatives for β-Amyloid Plaque Imaging

  摘要：

  In the present study, a styryltriazole and four resveratrol derivatives were synthesized as candidates for beta-amyloid (A beta) plaque imaging. On the basis of their binding affinities to A beta(1-42) aggregates, the styryltriazole (1, K-i = 12.8 nM) and one resveratrol derivative (5, K-i = 0.49 nM) were labeled with F-18. In normal mice, tissue distribution of [F-18]5 showed good initial brain uptake (3.26% ID/g at 2 min) but slow wash-out from brains (2-to-60 min uptake ratio: 2.9). Furthermore, it underwent in vivo metabolic defluorination (1.88% ID/g at 2 min and 9.73% ID/g at 60 min). In contrast, [F-18]1 displayed high initial brain uptake (5.38% ID/g at 2 min) with rapid wash-out from brains (0.52% ID/g at 60 min; 2-to-60 min uptake ratio: 10.3). These results indicate that [F-18]1 has in vivo kinetics comparable to PET radiopharmaceuticals currently under commercial development, demonstrating that [F-18]1 is a desirable PET radioligand for A beta plaque imaging.

  DOI：

  10.1021/jm201400q
• 作为产物：
  描述：

  4-(diethoxymethyl)-1-(2-hydroxyethyl)-1H-1,2,3-triazole 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 18.0h， 生成 4-(formyl)-1-(2-(methoxymethoxy)ethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and Evaluation of ¹⁸F-Labeled Styryltriazole and Resveratrol Derivatives for β-Amyloid Plaque Imaging

  摘要：

  In the present study, a styryltriazole and four resveratrol derivatives were synthesized as candidates for beta-amyloid (A beta) plaque imaging. On the basis of their binding affinities to A beta(1-42) aggregates, the styryltriazole (1, K-i = 12.8 nM) and one resveratrol derivative (5, K-i = 0.49 nM) were labeled with F-18. In normal mice, tissue distribution of [F-18]5 showed good initial brain uptake (3.26% ID/g at 2 min) but slow wash-out from brains (2-to-60 min uptake ratio: 2.9). Furthermore, it underwent in vivo metabolic defluorination (1.88% ID/g at 2 min and 9.73% ID/g at 60 min). In contrast, [F-18]1 displayed high initial brain uptake (5.38% ID/g at 2 min) with rapid wash-out from brains (0.52% ID/g at 60 min; 2-to-60 min uptake ratio: 10.3). These results indicate that [F-18]1 has in vivo kinetics comparable to PET radiopharmaceuticals currently under commercial development, demonstrating that [F-18]1 is a desirable PET radioligand for A beta plaque imaging.

  DOI：

  10.1021/jm201400q

文献信息

• Synthesis and Evaluation of ¹⁸F-Labeled Styryltriazole and Resveratrol Derivatives for β-Amyloid Plaque Imaging
  作者：Iljung Lee、Yearn Seong Choe、Joon Young Choi、Kyung-Han Lee、Byung-Tae Kim

  DOI：10.1021/jm201400q

  日期：2012.1.26

  In the present study, a styryltriazole and four resveratrol derivatives were synthesized as candidates for beta-amyloid (A beta) plaque imaging. On the basis of their binding affinities to A beta(1-42) aggregates, the styryltriazole (1, K-i = 12.8 nM) and one resveratrol derivative (5, K-i = 0.49 nM) were labeled with F-18. In normal mice, tissue distribution of [F-18]5 showed good initial brain uptake (3.26% ID/g at 2 min) but slow wash-out from brains (2-to-60 min uptake ratio: 2.9). Furthermore, it underwent in vivo metabolic defluorination (1.88% ID/g at 2 min and 9.73% ID/g at 60 min). In contrast, [F-18]1 displayed high initial brain uptake (5.38% ID/g at 2 min) with rapid wash-out from brains (0.52% ID/g at 60 min; 2-to-60 min uptake ratio: 10.3). These results indicate that [F-18]1 has in vivo kinetics comparable to PET radiopharmaceuticals currently under commercial development, demonstrating that [F-18]1 is a desirable PET radioligand for A beta plaque imaging.