tert-butyl (2-(6-(dimethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)carbamate | 1051373-04-6

• 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: tert-butyl (2-(6-(dimethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)carbamate
• 英文别名: tert-butyl 2-(4-dimethylamino-1,8-naphthalimide)ethylcarbamate；tert-butyl N-[2-[6-(dimethylamino)-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl]carbamate
• CAS: 1051373-04-6
• 化学式: C₂₁H₂₅N₃O₄
• 分子量: 383.447
• InChiKey: KEEFCXQLFZAHKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-(6-(dimethylamino)-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 3.0h， 生成 2-(2-氨基乙基)-6-(二甲基氨基)-1H-苯并[DE]异喹啉-1,3(2H)-二酮
  参考文献：
  名称：

  含氮杂环丁烷的杂环杂环可增强荧光团的性能。

  摘要：

  荧光染料广泛用于各种荧光成像技术中。但是，许多现有的修饰策略无法平衡荧光团的性能（例如亮度，光稳定性，水溶性和渗透性）。本文中，我们报告了通过将含氮杂环丁烷的杂螺环引入常用的荧光支架中来增强供体-受体型荧光团性能的一般策略。事实证明，这种策略是开发高质量荧光团的一般方法。

  DOI：

  10.1021/acs.orglett.0c01414
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 三乙胺 作用下， 以 乙醇 、 乙二醇甲醚 为溶剂， 反应 16.0h， 生成 tert-butyl (2-(6-(dimethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)carbamate
  参考文献：
  名称：

  含氮杂环丁烷的杂环杂环可增强荧光团的性能。

  摘要：

  荧光染料广泛用于各种荧光成像技术中。但是，许多现有的修饰策略无法平衡荧光团的性能（例如亮度，光稳定性，水溶性和渗透性）。本文中，我们报告了通过将含氮杂环丁烷的杂螺环引入常用的荧光支架中来增强供体-受体型荧光团性能的一般策略。事实证明，这种策略是开发高质量荧光团的一般方法。

  DOI：

  10.1021/acs.orglett.0c01414

文献信息

• 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。
• Novel side-chain alternative copolymer combined FRET and DRET with large pseudo-Stokes shift and polarity-sensitive fluorescence behavior
  作者：Yan Yu、Bohao Yang、Yongjie Yuan、Hailiang Zhang

  DOI：10.1039/c9tc03421h

  日期：——

  both as emissive donor in the aggregation state and dark donor in solution, this copolymer exhibited fluorescence resonance energy transfer (FRET) and dark resonance energy transfer (DRET) processes from TPE to NI, so it remained emissive whether in solution or aggregation state, and the fluorescence intensity of NI was increased obviously compared to when it was excited directly without energy transfer

  设计并合成了一种新颖的替代共聚物，该共聚物将四苯乙烯（TPE）和萘二甲酰亚胺（NI）掺入苯乙烯和马来酸酐作为侧链。归因于TPE单元既在聚集态中充当发射供体，又在溶液中充当深色供体，该共聚物表现出从TPE到NI的荧光共振能量转移（FRET）和暗共振能量转移（DRET）过程，因此无论是否在与在没有能量转移的情况下直接激发相比，NI的荧光强度明显增加。此外，该替代共聚物在聚集状态下显示出令人印象深刻的伪斯托克斯位移，其位移高达215 nm，大于所有其他已报道体系的FRET和DRET组合结果。最后，
• Naphthalimide and quinoline derivatives as inhibitors for insect N-acetyl-β-d-hexosaminidase
  作者：Huibin Yang、Huitang Qi、Tian Liu、Xusheng Shao、Qing Yang、Xuhong Qian

  DOI：10.1016/j.cclet.2019.01.023

  日期：2019.5

  Insect chitinolytic beta-N-acetyl-D-hexosaminidase, such as OfHex1 from Ostrinia furnacalis, is a potential target for insecticide design. Among the known OfHex1 inhibitors, Q2 is of great interest because it is the first non-carbohydrate inhibitor. In this study, we designed and synthesized a series of Q2 derivatives by replacing the thiadiazole and naphthalimide groups and changing the linker length. Compound 3m showed the best inhibitory activity with a K-i value of 034 mu mol/L against OfHex1, which is about one-quarter that of Q2 (K-i = 1.4 mu mol/L). Compound 6a showed the best inhibitory activity among the quinoline-containing derivatives (K-i = 2.3 mu mol/L). Molecular docking indicated that although 3m, 6a, and Q2 binding the active pocket of OfHex1 in similar mode, compound 3m engaged better than the other compounds in intermolecular interaction with OfHex1. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• 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.
• ENVIRONMENTALLY SENSITIVE FLUOROPHORES
  申请人：Imperiali Barbara

  公开号：US20100168428A1

  公开（公告）日：2010-07-01

  The present invention generally relates to environment-sensitive fluorophores, including environment-sensitive fluorophores for reporting protein/protein and peptide/protein interactions. In one aspect, the present invention is directed to compounds and salts thereof, compositions and methods useful in determining biological interactions. In some cases, the compounds of the present invention are environment-sensitive fluorophores that have spectroscopic behavior that may depend on factors such as the physicochemical properties of the surrounding environment. The compounds of the present invention can be used, in certain embodiments, to monitor ions, small molecules, and biological processes such as protein folding, protein-protein interactions and phosphorylation events.