2-((2-((6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl)(methyl)amino)ethyl)(2-(4-methoxybenzylthio)ethyl)amino)-N-(2-(4-methoxybenzylthio)ethyl)acetamide | 1276041-67-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-((2-((6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl)(methyl)amino)ethyl)(2-(4-methoxybenzylthio)ethyl)amino)-N-(2-(4-methoxybenzylthio)ethyl)acetamide
• CAS: 1276041-67-8
• 化学式: C₄₀H₄₅N₅O₃S₂
• 分子量: 707.961
• InChiKey: BGVNAEPDEZBBIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  50.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101.62
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-((2-((6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl)(methyl)amino)ethyl)(2-(4-methoxybenzylthio)ethyl)amino)-N-(2-(4-methoxybenzylthio)ethyl)acetamide 在 甲烷磺酸 、 苯甲醚 、 三氟乙酸 作用下， 反应 1.5h， 以57.01%的产率得到2-((2-((6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl)(methyl)amino)ethyl)(2-mercaptoethyl)amino)-N-(2-mercaptoethyl)acetamide
  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
• 作为产物：
  描述：

  2-(1-{6-[(2-hydroxyethyl)(methyl)amino]-2-naphthyl}ethylidene)malononitrile 在 N-溴代丁二酰亚胺(NBS) 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 38.17h， 生成 2-((2-((6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl)(methyl)amino)ethyl)(2-(4-methoxybenzylthio)ethyl)amino)-N-(2-(4-methoxybenzylthio)ethyl)acetamide
  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