5-amino-2-(2-bromoethyl)isoindole-1,3-dione | 437715-63-4

• 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: 5-amino-2-(2-bromoethyl)isoindole-1,3-dione
• 英文别名: 5-Amino-2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione
• CAS: 437715-63-4
• 化学式: C₁₀H₉BrN₂O₂
• 分子量: 269.098
• InChiKey: ZNQAYUWDCRXHMO-UHFFFAOYSA-N

物化性质

• 沸点：
  435.0±30.0 °C(Predicted)
• 密度：
  1.729±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-2-(2-bromoethyl)isoindole-1,3-dione 、 N,N-bis(2-(ethylthio)ethyl)amine 在 sodium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以40%的产率得到5-Amino-2-[2-[bis(2-ethylsulfanylethyl)amino]ethyl]isoindole-1,3-dione
  参考文献：
  名称：

  A highly selective ‘off–on’ fluorescence chemosensor for Cr(III)

  摘要：

  An 'off-on' fluorescence chemosensor for the selective signalling of Cr(III) has been designed exploiting the guest-induced inhibition of the photoinduced electron transfer signalling mechanism. The system shows an approximately 17-fold Cr(III)-selective chelation-enhanced fluorescence response in tetrahydrofuran and the system is highly selective against the background of environmentally and biologically relevant metal ions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.091
• 作为产物：
  描述：

  4-硝基邻苯二甲酰亚胺 在 palladium on activated charcoal 、 甲酸铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 16.0h， 生成 5-amino-2-(2-bromoethyl)isoindole-1,3-dione
  参考文献：
  名称：

  A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors

  摘要：

  Several members of a new family of non-sugar-type alpha-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast alpha-glycosidase and rat intestinal alpha-glycosidase. Almost all the compounds had strong inhibitory activities against yeast alpha-glycosidase. Regarding rat intestinal alpha-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal alpha-amylase. Structure-activity relationship studies indicated that 5-(p-toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the alpha-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.011

文献信息

• Fluorescence response of mono- and tetraazacrown derivatives of 4-aminophthalimide with and without some transition and post transition metal ions
  作者：N. B. SankaranPresent address: Department、Prasun K. Mandal、Bhaswati Bhattacharya、Anunay Samanta

  DOI：10.1039/b417926a

  日期：——

  The fluorescence response of two fluorophore–spacer–receptor systems, 1 and 2, wherein a 4-aminophthalimido moiety is linked to a monoaza- and a tetraazacrown macrocycle via a dimethylene spacer, has been explored in the absence and in the presence of various transition and post transition metal ions. Unlike the parent fluorophore, these systems are weakly fluorescent because of photoinduced electron transfer (PET) between the terminal moieties of the molecules. Of the two systems, PET is found to be more efficient in 2, which contains the tetraazacrown moiety as the receptor. Both systems display complex fluorescence decay behaviour with the average fluorescence lifetime much shorter than that of the parent fluorophore. The systems exhibit fluorescence enhancement in the presence of the metal ions, some of which are notorious quenchers of fluorescence. While the fluorescence output of 1 is rather similar with different metal ions, 2 exhibits high fluorescence enhancement with metal ions such as Zn2+, Cd2+, Pb2+, Hg2+ and Mn2+ while producing negligible enhancement with the remaining metal ions studied. This specific signaling behaviour of 2 has been rationalized taking into consideration somewhat unusual binding ability of the tetraazacrown receptor moiety.

  两种荧光团-间隔物-受体系统 1 和 2（其中一个 4-氨基邻苯二甲酰亚胺分子通过二亚甲基间隔物连接到一个单氮冠和一个四氮冠大环）在没有和有各种过渡和后过渡金属离子的情况下的荧光响应已经得到了探讨。与母体荧光团不同的是，由于分子末端分子之间存在光诱导电子转移（PET），因此这些系统的荧光很弱。在这两种体系中，2 的 PET 效率更高，因为它含有作为受体的四氮冠分子。这两种体系都显示出复杂的荧光衰减行为，平均荧光寿命比母体荧光团短得多。在金属离子存在的情况下，这些系统的荧光会增强，而其中一些金属离子是臭名昭著的荧光淬灭剂。1 在不同金属离子作用下的荧光输出相当相似，而 2 在 Zn2+、Cd2+、Pb2+、Hg2+ 和 Mn2+ 等金属离子作用下的荧光增强很高，而在研究的其余金属离子作用下的荧光增强可以忽略不计。考虑到四氮唑冠受体分子不同寻常的结合能力，2 的这种特殊信号行为得到了合理解释。
• Calix[4]azacrown and 4-aminophthalimide-appended calix[4]azacrown: synthesis, structure, complexation and fluorescence signaling behaviour
  作者：Sandip Banthia、Anunay Samanta

  DOI：10.1039/b500912j

  日期：——

  The synthesis and single crystal structure of 25,27-(diamidomonoazacrown-5)-calix[4]arene (L), calix[4]arene capped by a diamide bridge in the 1,3-position on the lower rim, which forms a supramolecular dimer in the solid state via intermolecular hydrogen bonding, are described. A 4-aminophthalimide (AP) fluorophore has been regioselectively linked to the secondary amino function of the azacrown unit

  25,27-（diamidomonoazacrown-5）-calix [4] arene（L），calix [4] arene的合成和单晶结构在下缘的1,3-位上被双酰胺桥覆盖描述了通过分子间氢键在固态的超分子二聚体。已使用二亚甲基间隔基将4-氨基邻苯二甲酰亚胺（AP）荧光团区域选择性地连接至氮杂冠单元的仲氨基功能，以通过荧光团构建N-（4-氨基邻苯二甲酰亚胺基乙基）杯[4]氮杂row（APL），一种荧光传感器。 -spacer-receptor体系结构。由于分子的荧光团和受体部分之间发生了光诱导的分子内电子转移（PIET），因此已测量出APL的荧光量子产率和寿命低于裸荧光团（AP）。在过渡金属离子的存在下，观察到的荧光增强表明金属离子与传感器结合。使用紫外可见光谱研究了APL与过渡金属离子的络合特性。从工作图确定配合物的化学计量比为1：1，并评估各种金属离子的相应缔合常数。与其他金属离
• Multiple Logical Access with a Single Fluorophore-Spacer-Receptor System: Realization of Inhibit (INH) Logic Function
  作者：Sandip Banthia、Anunay Samanta

  DOI：10.1002/ejoc.200500617

  日期：2005.12

  Zn2+, Cd2+, or Pb2+ (OR logic). X-ray structure analyses of 1 and its Zn2+ complex reveal that the solid-state conformation is in accordance with the results observed in solution. Sensor 1 also acts as an “Off-On-Off” switch stimulated by protons. The H+-driven “Off-On-Off” switch is integrated with a Zn2+-, Cd2+-, or Pb2+-induced OR logic gate to construct a first INH logic gate employing these ionic

  已经合成了一种新的荧光 PET 传感器 (1)，在存在 Zn2+、Cd2+ 或 Pb2+（OR 逻辑）的情况下，其荧光会“开启”并呈现蓝绿色变化。1 及其 Zn2+ 配合物的 X 射线结构分析表明，固态构象与在溶液中观察到的结果一致。传感器 1 还充当由质子激发的“关-开-关”开关。H+ 驱动的“关-开-关”开关与 Zn2+-、Cd2+- 或 Pb2+ 诱导的 OR 逻辑门集成，以构建使用这些离子输入的第一个 INH 逻辑门。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis, photophysical and metal ion signalling behaviour of mono- and di-azacrown derivatives of 4-aminophthalimide
  作者：N B Sankaran、M Sarkar、A Samanta

  DOI：10.1007/bf03356103

  日期：2005.3
• A highly selective ‘off–on’ fluorescence chemosensor for Cr(III)
  作者：Moloy Sarkar、Sandip Banthia、Anunay Samanta

  DOI：10.1016/j.tetlet.2006.08.091

  日期：2006.10

  An 'off-on' fluorescence chemosensor for the selective signalling of Cr(III) has been designed exploiting the guest-induced inhibition of the photoinduced electron transfer signalling mechanism. The system shows an approximately 17-fold Cr(III)-selective chelation-enhanced fluorescence response in tetrahydrofuran and the system is highly selective against the background of environmentally and biologically relevant metal ions. (c) 2006 Elsevier Ltd. All rights reserved.