6-(4-methylpiperazin-1-yl)naphthalene-2-carbaldehyde | 1290035-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-(4-methylpiperazin-1-yl)naphthalene-2-carbaldehyde
• 英文别名: 6-(4-Methylpiperazin-1-yl)naphthalene-2-carbaldehyde
• CAS: 1290035-73-2
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: KQEPSUUBLOEQOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甘醇单甲醚 、 6-(4-methylpiperazin-1-yl)naphthalene-2-carbaldehyde 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以85%的产率得到(E)-2-(2-(2-methoxyethoxy)ethoxy)ethyl 2-cyano-3-(2-(4-methylpiperazin-1-yl) napthalen-6-yl)acrylate
  参考文献：
  名称：

  Aminonaphthalene 2-Cyanoacrylate (ANCA) Probes Fluorescently Discriminate between Amyloid-β and Prion Plaques in Brain

  摘要：

  A major challenge for diagnosing and monitoring the progression of amyloid-based diseases is the capability to distinguish between amyloid deposits that are associated with related, but distinctly different, diseases. Here, we demonstrate that aminonaphthalenyl 2-cyanoacrylate-based probes can fluorescently discriminate between different types of amyloid deposits in brain. The discriminating capability of these molecular rotors is due to the stabilization of the ground versus excited states of these probes as a function of the polarity of their microenvironment (i.e., within the binding pocket on the amyloid). This property makes it possible, for the first time, to estimate the inherent static relative permittivity (epsilon(0)) of the binding pocket of each amyloid within tissue. The capability to selectively follow the deposition of specific amyloids in tissue may provide important information for therapeutic development that is not readily accessible from currently available technology.

  DOI：

  10.1021/ja3063698
• 作为产物：
  描述：

  6-溴-2-萘甲醇 在 三叔丁基膦 、 palladium diacetate 、 caesium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 77.0h， 生成 6-(4-methylpiperazin-1-yl)naphthalene-2-carbaldehyde
  参考文献：
  名称：

  Aminonaphthalene 2-Cyanoacrylate (ANCA) Probes Fluorescently Discriminate between Amyloid-β and Prion Plaques in Brain

  摘要：

  A major challenge for diagnosing and monitoring the progression of amyloid-based diseases is the capability to distinguish between amyloid deposits that are associated with related, but distinctly different, diseases. Here, we demonstrate that aminonaphthalenyl 2-cyanoacrylate-based probes can fluorescently discriminate between different types of amyloid deposits in brain. The discriminating capability of these molecular rotors is due to the stabilization of the ground versus excited states of these probes as a function of the polarity of their microenvironment (i.e., within the binding pocket on the amyloid). This property makes it possible, for the first time, to estimate the inherent static relative permittivity (epsilon(0)) of the binding pocket of each amyloid within tissue. The capability to selectively follow the deposition of specific amyloids in tissue may provide important information for therapeutic development that is not readily accessible from currently available technology.

  DOI：

  10.1021/ja3063698

文献信息

• AMYLOID BINDING AGENTS
  申请人：The Regents of the University of California

  公开号：US20150177262A1

  公开（公告）日：2015-06-25

  There are provided compounds and methods for the detection of amyloids and treatment of diseases related to amyloids including Alzheimer's disease and other related amyloid-based neurodegenerative diseases.

  提供了化合物和方法，用于检测淀粉样蛋白和治疗与淀粉样蛋白相关的疾病，包括阿尔茨海默病和其他相关的淀粉样蛋白相关神经退行性疾病。
• 10.1021/acs.jmedchem.4c00252
  作者：Liu, Bing、Li, Xiaofang、Liu, Zhengyang、He, Bing、Xu, Hanyue、Cao, Jianqin、Zeng, Fantian、Feng, Haiwei、Ren, Yanwei、Li, Haoyu、Wang, Tianyu、Li, Jia、Ye, Yuting、Zhao, Li、Ran, Chongzhao、Li, Yuyan

  DOI：10.1021/acs.jmedchem.4c00252

  日期：——

  Amyloid-β oligomers (AβOs), crucial toxic proteins in early Alzheimer’s disease (AD), precede the formation of Aβ plaques and cognitive impairment. In this context, we present our iterative process for developing novel near-infrared fluorescent (NIRF) probes specifically targeting AβOs, aimed at early AD diagnosis. An initial screening identified compound 18 as being highly selective for AβOs. Subsequent

  β 淀粉样蛋白寡聚体 (AβO) 是早期阿尔茨海默病 (AD) 中的关键有毒蛋白，先于 Aβ 斑块和认知障碍的形成。在此背景下，我们介绍了开发专门针对 AβO 的新型近红外荧光 (NIRF) 探针的迭代过程，旨在早期 AD 诊断。初步筛选确定化合物18对 AβO 具有高度选择性。随后的分析表明，化合物20改善了血清稳定性，同时保留了对 AβO 的亲和力。最有前途的迭代化合物37表现出卓越的品质：对 AβO 的高亲和力、近红外区域的发射以及良好的生物相容性。值得注意的是，离体双染色表明化合物37在 AD 小鼠大脑中检测到了 AβO，体内成像实验表明化合物37可以区分 4 个月大的 AD 小鼠和年龄匹配的野生型小鼠。因此，化合物37已成为AD早期检测的有价值的NIRF探针和探索AD病理机制的有用工具。
• USES OF LABELED HSP90 INHIBITORS
  申请人：Sloan Kettering Institute For Cancer Research

  公开号：EP3208615B1

  公开（公告）日：2019-10-09
• [EN] USES OF LABELED HSP90 INHIBITORS<br/>[FR] UTILISATIONS D'INHIBITEURS MARQUÉS DE HSP90
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2013009655A3

  公开（公告）日：2013-05-10
• US8940918B2
  申请人：——

  公开号：US8940918B2

  公开（公告）日：2015-01-27