2-chloro-N-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-acetamide | 62578-90-9

• 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-chloro-N-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-acetamide
• 英文别名: 2-chloro-N-(1,3-dioxobenzo[de]isoquinolin-2-yl)acetamide
• CAS: 62578-90-9
• 化学式: C₁₄H₉ClN₂O₃
• 分子量: 288.69
• InChiKey: ZFCIPEJQXQCPFR-UHFFFAOYSA-N

物化性质

• 熔点：
  241-242 °C
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-acetamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  两种水溶性1,8-萘二甲酰亚胺的合成，荧光传感和分子逻辑。

  摘要：

  合成并研究了两种新型的高度水溶性的荧光传感1,8-萘二甲酰亚胺。该新型化合物是在“荧光团-受体1-间隔子-受体2”模型上设计的，作为一种分子荧光探针，用于测定100％水性介质中的阳离子和阴离子。包含N-酰亚胺和N-苯基哌嗪或吗啉取代基的新型探针能够通过ICT和PET信号传导机制同时作为pH的函数运行，并能够选择性识别其他代表性金属离子上的Cu2 +和Hg2 +。由于质子，氢氧根离子，Hg2 +和Cu2 +的存在下荧光发生了显着变化，因此执行了INH和双重禁用的INH逻辑门，并且该系统能够充当具有四个化学输入的单个输出组合逻辑电路。

  DOI：

  10.1016/j.saa.2017.04.016
• 作为产物：
  描述：

  1,8-萘二甲酸酐 在 一水合肼 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.0h， 生成 2-chloro-N-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-acetamide
  参考文献：
  名称：

  两种水溶性1,8-萘二甲酰亚胺的合成，荧光传感和分子逻辑。

  摘要：

  合成并研究了两种新型的高度水溶性的荧光传感1,8-萘二甲酰亚胺。该新型化合物是在“荧光团-受体1-间隔子-受体2”模型上设计的，作为一种分子荧光探针，用于测定100％水性介质中的阳离子和阴离子。包含N-酰亚胺和N-苯基哌嗪或吗啉取代基的新型探针能够通过ICT和PET信号传导机制同时作为pH的函数运行，并能够选择性识别其他代表性金属离子上的Cu2 +和Hg2 +。由于质子，氢氧根离子，Hg2 +和Cu2 +的存在下荧光发生了显着变化，因此执行了INH和双重禁用的INH逻辑门，并且该系统能够充当具有四个化学输入的单个输出组合逻辑电路。

  DOI：

  10.1016/j.saa.2017.04.016

文献信息

• A Highly Water-Soluble and Solid State Emissive 1,8-Naphthalimide as a Fluorescent PET Probe for Determination of pHs, Acid/Base Vapors, and Water Content in Organic Solvents
  作者：Nikolai I. Georgiev、Paoleta V. Krasteva、Ventsislav V. Bakov、Vladimir B. Bojinov

  DOI：10.3390/molecules27134229

  日期：——

  the INH logic gate was achieved using NaOH and water as chemical inputs, where NaOH is the disabler and the water is an enabler. In addition, the probe showed effective fluorescence “off-on” reversibility on glass support after exposure to acid and base vapors, which defines it as a promising platform for rapid detection of acid/base vapors in the solid-state, thus extending the molecular sensing concept

  合成了基于“荧光团-间隔区-受体1-受体2 ”模型设计的新型高水溶性1,8-萘酰亚胺荧光团。由于在水中的异常高溶解度，这种新型化合物被证明是一种选择性的基于 PET 的探针，用于测定水溶液中的 pH 值和快速检测有机溶剂中的水含量。基于探针的 pH 依赖性及其高水溶性，INH 逻辑门是使用 NaOH 和水作为化学输入实现的，其中 NaOH 是禁用剂，水是促进剂。此外，该探针显示出有效的荧光“ off-on ”” 玻璃载体在暴露于酸和碱蒸气后的可逆性，这将其定义为快速检测固态酸/碱蒸气的有前途的平台，从而将分子传感概念从溶液扩展到固体载体。
• 2-Hexylaminoethylamidonaphthalimide as Cu2+ sensor
  作者：T. Sheshashena Reddy、A. Ram Reddy

  DOI：10.1016/j.saa.2014.02.120

  日期：2014.7

  New fluorescent hexylaminoalkylamidonaphthalimides were synthesized and their fluorescence was investigated in different solvents. The fluorescence intensity of hexylaminoalkylamidonaphthalimides is directly related to the number of carbons in the intervening chain between the naphthalimide and n-hexylamine. Among the hexylaminoalkylamidonaphthalimides, 2-hexylaminoethylamidonaphthalimide was developed into a new fluorogenic probe. The bidentate 2-hexylaminoethylamidonaphthalimide acted as fluorescent chemosensor with a high selectivity and suitable affinity towards Cu2+ in aqueous medium (pH 7.4). This technique of detection of Cu2+ is highly sensitive and can detect 0.1 mu M range. (C) 2014 Elsevier B.V. All rights reserved.
• Selective inhibition of β-N-acetylhexosaminidases by thioglycosyl–naphthalimide hybrid molecules
  作者：Wei Chen、Shengqiang Shen、Lili Dong、Jianjun Zhang、Qing Yang

  DOI：10.1016/j.bmc.2017.11.042

  日期：2018.1

  To develop selective inhibitors for beta-N-acetylhexosaminidases which are involved in a myriad of physiological processes, a series of novel thioglycosyl-naphthalimide hybrid inhibitors were designed, synthesized and evaluated for inhibition activity against glycosyl hydrolase family 20 and 84 (GH20 and GH84) beta-N-acetylhexosaminidases. These compounds which incorporate groups with varied sizes and lengths at the linker region between thioglycosyl moiety and naphthalimide moiety are designed to improve the selectivity and stacking interactions. The GH84 human O-GlcNAcase (hOGA) was sensitive to the subtle changes in the linker region and the optimal choice is a small size linker with six atoms length. And the GH20 insect beta-N-acetylhexosaminidase OfHex1 could tolerate compounds with a hydrophobic bulky linker. Especially, the compound 5c (hOGA, K-i = 3.46 mu M; OfHex1, K-i > 200 mu M) and the compound 6f (hOGA, K-i > 200 mu M; OfHex1, K-i = 21.81 mu M) displayed high selectivity. The molecular docking results indicated that the inhibition mechanism was different between the two families due to their different structural characteristics beyond the active sites. These results provide some promising clues to improve selectivity of potent molecules against beta-N-acetylhexosaminidases. (C) 2017 Elsevier Ltd. All rights reserved.
• KRASOVITSKIJ B. M.; OSTIS L. L.; SHEVCHENKO EH. A.; NESTERKINA I. G.; ISA+, V SB. CZHINTILLYATORY I ORGAN. LYUMINOFORY BZHP. 4. XARKOV, 1975, 5-15
  作者：KRASOVITSKIJ B. M.、 OSTIS L. L.、 SHEVCHENKO EH. A.、 NESTERKINA I. G.、 ISA+

  DOI：——

  日期：——