(E)-1-(2-methanesulfonyloxyethyl)-4-(4-N,N-dimethylaminostyryl)-1H-1,2,3-triazole | 1354569-85-9

• 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: (E)-1-(2-methanesulfonyloxyethyl)-4-(4-N,N-dimethylaminostyryl)-1H-1,2,3-triazole
• 英文别名: 2-[4-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]triazol-1-yl]ethyl methanesulfonate
• CAS: 1354569-85-9
• 化学式: C₁₅H₂₀N₄O₃S
• 分子量: 336.415
• InChiKey: DMYVCIXECDALBU-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-methanesulfonyloxyethyl)-4-(4-N,N-dimethylaminostyryl)-1H-1,2,3-triazole 在 [18F]-tetrabutylammonium fluoride 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 (E)-1-(2-[18F]fluoroethyl)-4-(4-N,N-dimethylaminostyryl)-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：

  (E)-1-(2-hydroxyethyl)-4-(4-N,N-dimethylaminostyryl)-1H-1,2,3-triazole 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到(E)-1-(2-methanesulfonyloxyethyl)-4-(4-N,N-dimethylaminostyryl)-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.