2-(1-(6-((2-fluoroethyl)(methyl)amino)naphthalen-2-yl)ethylidene)malononitrile | 1260894-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-(6-((2-fluoroethyl)(methyl)amino)naphthalen-2-yl)ethylidene)malononitrile
• 英文别名: 1-(6-((2-fluoroethyl)(methyl)amino)naphthalen-2-yl)ethanone；FENE；1-[6-[(2-Fluoroethyl)methylamino]-2-naphthalenyl]ethanone；1-[6-[2-fluoroethyl(methyl)amino]naphthalen-2-yl]ethanone
• CAS: 1260894-66-3
• 化学式: C₁₅H₁₆FNO
• 分子量: 245.297
• InChiKey: IHYOXMQEVMCIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-乙酰基-2-萘酚 在 potassium disulphite 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 2-(1-(6-((2-fluoroethyl)(methyl)amino)naphthalen-2-yl)ethylidene)malononitrile
  参考文献：
  名称：

  99mTc- and Re-labeled 6-dialkylamino-2-naphthylethylidene derivatives as imaging probes for β-amyloid plaques

  摘要：

  Based on the conjugate strategy, two neutral Tc-99m labeled 2-(1-(6-(dialkylamino)naphthalen-2-yl) ethylidene) malononitrile (DDNP) and 1-(6-(dialkylamino) naphthalen-2-yl) ethanone (ENE) derivatives, and their corresponding rhenium complexes were synthesized. In vitro fluorescent staining indicated that the corresponding rhenium derivatives selectively stained the beta-amyloid (A beta) plaques in the brain sections of AD model mice with low background. Compared with FDDNP and FENE, the affinities of the corresponding rhenium derivatives to A beta aggregates decreased about 10-14-fold. In vivo biodistribution experiments in normal mice showed that Tc-99m-MAMA-ENE displayed medium initial brain uptake (0.65 % ID/g at 2 min) with a reasonable washout from the brain (0.19 % ID/g at 2 h) while (99mTc)-MAMA-DDNP showed a low brain uptake (0.28 % ID/g at 2 min). Further optimize these Tc-99m-labeled tracers in order to improve their binding affinities to A beta plaques and diffusion through the blood brain barrier may generate useful imaging agents for SPECT. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.096

文献信息

• The Value of In Vitro Binding as Predictor of In Vivo Results: A Case for [18F]FDDNP PET
  作者：Graham B. Cole、Nagichettiar Satyamurthy、Jie Liu、Koon-Pong Wong、Gary W. Small、Sung-Cheng Huang、Janez Košmrlj、Jorge R. Barrio、Andrej Petrič

  DOI：10.1007/s11307-018-1210-2

  日期：2019.2

  demonstrate the critical importance of rigorous experimental design for meaningful in vitro determinations. [18F]FDDNP binding to both amyloid plaques and neurofibrillary tangles was confirmed by amyloid and tau immunohistochemical stains of adjacent tissues. ConclusionsThis work illustrates the sensitivity of in vitro techniques to various experimental conditions and underscores that conclusions obtained

  目的当用used标记的生物标志物的体外结果被人为地批评体内数据和用正电子发射体和正电子发射断层显像（PET）标记的相同示踪剂得出的结论时，必须谨慎。本文通过PET [ 18 F] FDDNP的使用来说明这一概念，该[ 18 F] FDDNP是一种用于体内可视化人类β-淀粉样蛋白和tau蛋白神经聚集体的生物标记物，后来与[ 3 H] FDDNP报道的体外数据相矛盾。在这项调查中，我们分析了[ 3 H] FDDNP体外实验设计中涉及的多个因素 导致错误解释结果的研究。 程序本工作描述了[ 3 H] FDDNP的合成，表征，纯度和放射稳定性的动力学的全部细节。还介绍了使用[ 18 F] FDDNP和[ 3 H] FDDNP进行宏观和微观放射自显影检测tau和β-淀粉样蛋白聚集体的最佳体外条件。宏观放射自显影法的测定是使用先前文献中所述的既定方法，用已验证纯度的[ 3 H] FDDNP进行。 结果
• 99mTc- and Re-labeled 6-dialkylamino-2-naphthylethylidene derivatives as imaging probes for β-amyloid plaques
  作者：Mengchao Cui、Ruikun Tang、Zijing Li、Huiying Ren、Boli Liu

  DOI：10.1016/j.bmcl.2010.11.096

  日期：2011.2

  Based on the conjugate strategy, two neutral Tc-99m labeled 2-(1-(6-(dialkylamino)naphthalen-2-yl) ethylidene) malononitrile (DDNP) and 1-(6-(dialkylamino) naphthalen-2-yl) ethanone (ENE) derivatives, and their corresponding rhenium complexes were synthesized. In vitro fluorescent staining indicated that the corresponding rhenium derivatives selectively stained the beta-amyloid (A beta) plaques in the brain sections of AD model mice with low background. Compared with FDDNP and FENE, the affinities of the corresponding rhenium derivatives to A beta aggregates decreased about 10-14-fold. In vivo biodistribution experiments in normal mice showed that Tc-99m-MAMA-ENE displayed medium initial brain uptake (0.65 % ID/g at 2 min) with a reasonable washout from the brain (0.19 % ID/g at 2 h) while (99mTc)-MAMA-DDNP showed a low brain uptake (0.28 % ID/g at 2 min). Further optimize these Tc-99m-labeled tracers in order to improve their binding affinities to A beta plaques and diffusion through the blood brain barrier may generate useful imaging agents for SPECT. (C) 2010 Elsevier Ltd. All rights reserved.