2-(2-aminoethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1422463-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-aminoethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-(2-Aminoethyl)-6-methoxy-1H-benz[de]isoquinoline-1,3(2H)-dione；2-(2-aminoethyl)-6-methoxybenzo[de]isoquinoline-1,3-dione
• CAS: 1422463-10-2
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: WTJWXOVKBCITCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-aminoethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 氢碘酸 作用下， 反应 12.0h， 以86%的产率得到2-(2-amino-ethyl)-6-hydroxy-benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  A new ratiometric fluorescent probe for the detection of thiophenols

  摘要：

  报道了一种新的比例荧光探针，用于快速检测有毒的硫酚类化合物。

  DOI：

  10.1039/c5ra18977b
• 作为产物：
  描述：

  tert-butyl (2-(6-methoxy-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以85.2%的产率得到2-(2-aminoethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  硫糖基-萘二甲酰亚胺作为有效的和选择性的人O-GlcNAcase抑制剂的修饰。

  摘要：

  β-N-乙酰己糖胺酶是广泛分布的糖苷外切酶，由于其在农药和药物发现领域的重要作用而引起了广泛的关注。值得注意的是，人O-GlcNAcase（hOGA）和人β-N-乙酰基己糖胺酶（HsHex）具有相同的催化机制，但在体内发挥不同的生理作用。在这封信中，我们旨在提高先前报道的巯基糖基萘二甲酰亚胺对hOGA的抑制力和选择性。合理的化合物设计导致合成了带有4-哌啶基萘二甲酰亚胺部分的13r，作为高效的hOGA抑制剂（针对hOGA的Ki = 0.6μM）和良好的选择性（针对HsHexB的Ki> 100μM）。此外，为研究13r对hOGA的效力和选择性的基础，以及所选抑制剂的可能抑制机制（15b，使用分子对接和MD模拟研究了针对hOGA和HsHexB的13b和13r）。这些4-取代的萘二甲酰亚胺硫代糖苷可能潜在地用作进一步研究hOGA功能的有用工具。

  DOI：

  10.1021/acsmedchemlett.8b00406

文献信息

• Development of Unsymmetrical Dyads As Potent Noncarbohydrate-Based Inhibitors against Human β-<i>N</i>-Acetyl-<scp>d</scp>-hexosaminidase
  作者：Peng Guo、Qi Chen、Tian Liu、Lin Xu、Qing Yang、Xuhong Qian

  DOI：10.1021/ml300475m

  日期：2013.6.13

  Human beta-N-acetyl-D-hexosaminidase has gained much attention due to its roles in several pathological processes and been considered as potential targets for disease therapy. A novel and efficient skeleton, which was an unsymmetrical dyad containing naphthalimide and methoxyphenyl moieties with an alkylamine spacer linkage as a noncarbohydrate-based inhibitor, was synthesized, and the activities were valuated against human beta-N-acetyl-D-hexosaminidase. The most potent inhibitor exhibits high inhibitory activity with K-i values of 0.63 mu M. The straightforward synthetic manner of these unsymmetrical dyads and understanding of the binding model cold be advantageous for further structure optimization and development of new therapeutic agents for Hex-related diseases.
• Exploring unsymmetrical dyads as efficient inhibitors against the insect β-N-acetyl-d-hexosaminidase OfHex2
  作者：Qi Chen、Peng Guo、Lin Xu、Tian Liu、Xuhong Qian、Qing Yang

  DOI：10.1016/j.biochi.2013.10.008

  日期：2014.2

  The GH20 beta-N-acetyl-D-hexosaminidase OfHex2 from the insect Ostrinia furnacalis (Guenee) is a target potential for eco-friendly pesticide development. Although carbohydrate-based inhibitors against beta-Nacetyl-D-hexosaminidases are widely studied, highly efficient, non-carbohydrate inhibitors are more attractive due to low cost and readily synthetic manner. Based on molecular modeling analysis of the catalytic domain of OfHex2, a series of novel naphthalimide-scaffold conjugated with a small aromatic moiety by an alkylamine spacer linker were designed and evaluated as efficiently competitive inhibitors against OfHex2. The most potent one containing naphthalimide and phenyl groups spanning by an N-alkylamine linker has a K-i value of 0.37 mu M, which is 6 fold lower than that of M-31850, the most potent non-carbohydrate inhibitor ever reported. The straightforward synthetic manners as well as the presumed binding model in this paper could be advantageous for further structural optimization for developing inhibitors against GH20 beta-N-acetyl-D-hexosaminidases. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Modification of the Thioglycosyl–Naphthalimides as Potent and Selective Human O-GlcNAcase Inhibitors
  作者：Shengqiang Shen、Lili Dong、Wei Chen、Xiangdi Zeng、Huizhe Lu、Qing Yang、Jianjun Zhang

  DOI：10.1021/acsmedchemlett.8b00406

  日期：2018.12.13

  the synthesis of 13r bearing a 4-piperidylnaphthalimide moiety as a highly potent hOGA inhibitor (K i = 0.6 μM against hOGA) with good selectivity (K i > 100 μM against HsHexB). Furthermore, to investigate the basis for the potency and selectivity of 13r against hOGA, the possible inhibitory mechanisms of selected inhibitors (15b, 13b, and 13r) against hOGA and HsHexB were studied using molecular docking

  β-N-乙酰己糖胺酶是广泛分布的糖苷外切酶，由于其在农药和药物发现领域的重要作用而引起了广泛的关注。值得注意的是，人O-GlcNAcase（hOGA）和人β-N-乙酰基己糖胺酶（HsHex）具有相同的催化机制，但在体内发挥不同的生理作用。在这封信中，我们旨在提高先前报道的巯基糖基萘二甲酰亚胺对hOGA的抑制力和选择性。合理的化合物设计导致合成了带有4-哌啶基萘二甲酰亚胺部分的13r，作为高效的hOGA抑制剂（针对hOGA的Ki = 0.6μM）和良好的选择性（针对HsHexB的Ki> 100μM）。此外，为研究13r对hOGA的效力和选择性的基础，以及所选抑制剂的可能抑制机制（15b，使用分子对接和MD模拟研究了针对hOGA和HsHexB的13b和13r）。这些4-取代的萘二甲酰亚胺硫代糖苷可能潜在地用作进一步研究hOGA功能的有用工具。
• A new ratiometric fluorescent probe for the detection of thiophenols
  作者：Qisong Zhai、Shengjun Yang、Yuli Fang、Haiyan Zhang、Guoqiang Feng

  DOI：10.1039/c5ra18977b

  日期：——

  A new ratiometric fluorescent probe was reported for the rapid detection of toxic thiophenols.

  报道了一种新的比例荧光探针，用于快速检测有毒的硫酚类化合物。