2-(6-diethylaminohexyl)isoindoline-1,3-dione | 754227-30-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(6-diethylaminohexyl)isoindoline-1,3-dione
• 英文别名: N-(6-diethylamino-hexyl)-phthalimide；N-(6-Diaethylamino-hexyl)-phthalimid；2-[6-(Diethylamino)hexyl]isoindole-1,3-dione
• CAS: 754227-30-0
• 化学式: C₁₈H₂₆N₂O₂
• 分子量: 302.417
• InChiKey: AGCVARUNOXFJMW-UHFFFAOYSA-N

物化性质

• 熔点：
  206-208 °C
• 沸点：
  418.2±28.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(6-diethylaminohexyl)isoindoline-1,3-dione 在 氯甲酸乙酯 、 三乙胺 、 肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, biophysical and biological evaluation of 3,6-bis-amidoacridines with extended 9-anilino substituents as potent G-quadruplex-binding telomerase inhibitors

  摘要：

  Telomerase and telomere maintenance are emerging targets for the treatment of human cancers. We report here on the targeting of the telomere-telomerase complex with a series of small molecules based on an acridine platform. A series of 3,6-bis-amidoacridines with extended 9-anilino sidechains were designed and synthesised as potential telomeric G-quadruplex DNA (G4) interacting compounds. G4-stabilisation was assessed using a high-throughput FRET (fluorescence resonance energy transfer) assay and telomerase inhibition quantified by a modified TRAP (telomerase repeat amplification protocol) method. Within the series, the compounds showed significant G4-stabilising ability (DeltaT(m) values of 25-36degreesC at 1 muM concentration) and telomerase inhibition in the nanomolar region ((EC50)-E-tel values of 80-318 nM). Furthermore, a direct correlation between the FRET and TRAP assays was observed, supporting the use of the rapid screening FRET assay for early assessment of potential G4-stabilising telomerase inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.090
• 作为产物：
  描述：

  6-phthalimido-1-hexanol 在 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 2-(6-diethylaminohexyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis, biophysical and biological evaluation of 3,6-bis-amidoacridines with extended 9-anilino substituents as potent G-quadruplex-binding telomerase inhibitors

  摘要：

  Telomerase and telomere maintenance are emerging targets for the treatment of human cancers. We report here on the targeting of the telomere-telomerase complex with a series of small molecules based on an acridine platform. A series of 3,6-bis-amidoacridines with extended 9-anilino sidechains were designed and synthesised as potential telomeric G-quadruplex DNA (G4) interacting compounds. G4-stabilisation was assessed using a high-throughput FRET (fluorescence resonance energy transfer) assay and telomerase inhibition quantified by a modified TRAP (telomerase repeat amplification protocol) method. Within the series, the compounds showed significant G4-stabilising ability (DeltaT(m) values of 25-36degreesC at 1 muM concentration) and telomerase inhibition in the nanomolar region ((EC50)-E-tel values of 80-318 nM). Furthermore, a direct correlation between the FRET and TRAP assays was observed, supporting the use of the rapid screening FRET assay for early assessment of potential G4-stabilising telomerase inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.090

文献信息

• Novel Multitarget Directed Triazinoindole Derivatives as Anti-Alzheimer Agents
  作者：Dushyant V. Patel、Nirav R. Patel、Ashish M. Kanhed、Sagar P. Patel、Anshuman Sinha、Deep D. Kansara、Annie R. Mecwan、Sarvangee B. Patel、Pragnesh N. Upadhyay、Kishan B. Patel、Dharti B. Shah、Navnit K. Prajapati、Prashant R. Murumkar、Kirti V. Patel、Mange Ram Yadav

  DOI：10.1021/acschemneuro.9b00226

  日期：2019.8.21

  multitarget-directed ligands (MTDLs) to confront the key pathological aberrations. A novel series of triazinoindole derivatives were designed and synthesized. In vitro studies revealed that all the compounds showed moderate to good anticholinesterase activity; the most active compound 23e showed an IC50 value of 0.56 ± 0.02 μM for AChE and an IC50 value of 1.17 ± 0.09 μM for BuChE. These derivatives are also

  阿尔茨海默氏病（AD）的多面性要求使用多靶标配体（MTDL）进行治疗以应对关键的病理畸变。设计并合成了一系列新颖的三嗪并吲哚衍生物。体外研究表明，所有化合物均显示出中等至良好的抗胆碱酯酶活性。活性最高的化合物23e对AChE的IC50值为0.56±0.02μM，对BuChE的IC50值为1.17±0.09μM。这些衍生物还具有强大的抗氧化活性。为了理解化合物23e的合理结合模式，进行了分子对接研究和分子动力学模拟研究，结果表明23e在AChE和BuChE的活性位点之间发生了显着的相互作用。化合物23e成功地减轻了SH-SY5Y细胞中H2O2诱导的氧化应激，并以浓度依赖的方式对SH-SY5Y细胞表现出优异的抗 神经保护活性以及Aβ诱导的毒性。此外，在细胞毒性试验中，它对神经元SH-SY5Y细胞未显示任何明显的毒性。化合物23e在高达2000 mg / kg的剂量下未在大鼠中表现出任何急
• Design, Synthesis and Evaluation of Novel 2-(Aminoalkyl)-isoindoline-1,3-dione Derivatives as Dual-Binding Site Acetylcholinesterase Inhibitors
  作者：Michalina Ignasik、Marek Bajda、Natalia Guzior、Michaela Prinz、Ulrike Holzgrabe、Barbara Malawska

  DOI：10.1002/ardp.201100423

  日期：2012.7

  A new series of 2‐(diethylaminoalkyl)‐isoindoline‐1,3‐dione derivatives intended as dual binding site cholinesterase inhibitors were designed using molecular modeling and evaluated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), and the formation of the β‐amyloid (Aβ) plaques. For AChE inhibitory activity, the spectrophotometric method of Ellman and the electrophoretically

  使用分子模型设计了一系列旨在用作双结合位点胆碱酯酶抑制剂的新系列 2-(二乙氨基烷基)-异吲哚啉-1,3-二酮衍生物，并评估其作为乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶 (BuChE) 的抑制剂，以及β-淀粉样蛋白 (Aβ) 斑块。对于 AChE 抑制活性，使用 Ellman 的分光光度法和电泳介导的微量分析测定，给出了良好的结果。大多数合成的化合物具有 AChE 抑制活性，IC50 值范围从 IC50 = 0.9 到 19.5 µM，Aβ 抗聚集抑制活性较弱。这些结果支持对接研究的结果，该研究测试了针对 AChE 的催化活性位点 (CAS) 和外围阴离子位点 (PAS) 的化合物。
• 地氯雷他定衍生物、其制备方法及其用途
  申请人：天津市昕晨投资发展有限公司

  公开号：CN115385892A

  公开（公告）日：2022-11-25

  本申请公开了一种地氯雷他定衍生物、其制备方法及其用途，其中，–R为–R′或–Y–(CH2)–R′，Y为O或NH，n为1、2、3、4、5、或6，且–R′为二乙基氨基、吡咯烷基、哌嗪基、N‑吗啉基、双(2‑甲氧基乙基)氨基或4‑甲基哌嗪基。本申请并公开了一种合成如摘要附图所示的化合物的方法，还公开了如摘要附图所示的化合物，在制备缓解或治疗或预防过敏及其相关症状的药物的用途。如摘要附图所示的化合物为这一类型的药物提供了更多样的替代技术方案。
• N-Alkamine Substituted Phthalimides¹
  作者：M. B. Moore、R. T. Rapala

  DOI：10.1021/ja01212a089

  日期：1946.8