5-amino-2-[(methylsulfonyl)oxy]-1H-isoindole-1,3(2H)-dione | 105969-85-5

• 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-[(methylsulfonyl)oxy]-1H-isoindole-1,3(2H)-dione
• 英文别名: 6-amino-2-[(methylsulfonyl)oxy]-1H-isoindole-1,3-dione；5-Amino-2-((methylsulfonyl)oxy)-1H-isoindole-1,3(2H)-dione；(5-amino-1,3-dioxoisoindol-2-yl) methanesulfonate
• CAS: 105969-85-5
• 化学式: C₉H₈N₂O₅S
• 分子量: 256.239
• InChiKey: BNULMKWKKIYHKP-UHFFFAOYSA-N

物化性质

• 沸点：
  506.5±52.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-amino-2-[(methylsulfonyl)oxy]-1H-isoindole-1,3(2H)-dione 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  基于活动的人类嗜中性粒细胞弹性蛋白酶探针的设计：丢失重排的实现以诱导福斯特共振能量转移。

  摘要：

  人嗜中性粒细胞弹性蛋白酶是免疫反应的重要调节剂，并在宿主防御机制和进一步的生理过程中起作用。这种丝氨酸蛋白酶的不受控制的活性可能导致严重的组织改变并损害炎症状态。本文报道的基于人中性粒细胞弹性蛋白酶的基于活性的探针的设计依赖于磺酰氧基邻苯二甲酰亚胺部分作为连接至香豆素荧光团的新型战斗部。评估了基于活性的探针对几种丝氨酸和半胱氨酸蛋白酶的抑制能力，以及对人嗜中性粒细胞弹性蛋白酶的选择性（K i= 6.85 nM）。探针的适当荧光标签可在低纳摩尔范围内进行人嗜中性粒细胞弹性蛋白酶的凝胶内荧光检测。在Lossen重排过程中产生的探针的香豆素部分和邻氨基苯甲酸功能是两种不同的Förster共振能量转移的一部分。

  DOI：

  10.1021/acs.biochem.7b00906
• 作为产物：
  描述：

  N-羟基-4-硝基邻苯二甲酰亚胺 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 生成 5-amino-2-[(methylsulfonyl)oxy]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  基于活动的人类嗜中性粒细胞弹性蛋白酶探针的设计：丢失重排的实现以诱导福斯特共振能量转移。

  摘要：

  人嗜中性粒细胞弹性蛋白酶是免疫反应的重要调节剂，并在宿主防御机制和进一步的生理过程中起作用。这种丝氨酸蛋白酶的不受控制的活性可能导致严重的组织改变并损害炎症状态。本文报道的基于人中性粒细胞弹性蛋白酶的基于活性的探针的设计依赖于磺酰氧基邻苯二甲酰亚胺部分作为连接至香豆素荧光团的新型战斗部。评估了基于活性的探针对几种丝氨酸和半胱氨酸蛋白酶的抑制能力，以及对人嗜中性粒细胞弹性蛋白酶的选择性（K i= 6.85 nM）。探针的适当荧光标签可在低纳摩尔范围内进行人嗜中性粒细胞弹性蛋白酶的凝胶内荧光检测。在Lossen重排过程中产生的探针的香豆素部分和邻氨基苯甲酸功能是两种不同的Förster共振能量转移的一部分。

  DOI：

  10.1021/acs.biochem.7b00906

文献信息

• Effect of the amino versus the acylamino substituent on the product isomer distribution in the methanolysis of 5-(substituted)-2-[(methylsulfonyl)oxy]isoindole-1,3-diones
  作者：John E Kerrigan、Lisa M Vagnoni

  DOI：10.1016/s0040-4020(01)00827-4

  日期：2001.9

  The effect of the NH2 versus the CH3CONH and PhCH2CONH substituents at the 5-position in 5-(substituted)-2-[(methylsulfonyl)oxy]isoindole- 1,3-diones, on the product isomer distribution resulting from methanolysis, was investigated both experimentally and at the RHF/3-2 1 G(*), RHF/6-31 + G(*) and B3LYP/6-31 + G(*) levels of theory. The influence of solvent on the transition structure was investigated using the Onsager SCRF model. The influence of these substituents on the transition state (TS) leading to tetrahedral intermediate was studied. The 5-amino (para to C-1) function makes the C-1 carbonyl carbon more electron-rich and less reactive toward nucleophilic attack. A predominance of the isomer formed from initial nucleophilic attack at C-3 is observed for the NH2 substituent, whereas this selectivity is greatly reduced for the acylamino substituents. Examination of the LUMO from ab initio calculations performed on the starting materials at the RBF/6-31G(*) level give a good qualitative description of the regio selectivity observed from experiment. Calculated AE, values of this initial reaction step give a qualitative description of the experimentally observed regioselectivity in agreement with the LUMO model and resonance argument. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 6-Acylamino-2-[(alkylsulfonyl)oxy]-1 H -isoindole-1,3-dione mechanism-based inhibitors of human leukocyte elastase
  作者：John E Kerrigan、Matthew C Walters、Kerri J Forrester、Jason B Crowder、Lisa J Christopher

  DOI：10.1016/s0960-894x(99)00588-0

  日期：2000.1

  A study of various 2-[(alkylsulfonyl)oxy]-6-substituted-1H-isoindole-1,3-diones' inhibition of chymotrypsin compared to inhibition of HLE reveals that acylamino substitution in the 6-position increases selectivity and potency of these inhibitors for HLE. The best HLE inhibitor in this series was 6-(methylglutaryl)amino-2-[(ethylsulfonyl)oxy]-1H-isoindole-1,3-dione with a k(obs)/[I] = 220,000 M-1 s(-1). (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of 2-hydroxy-1H-isoindolediones as new cytostatic agents
  作者：Carcy L. Chan、Eric J. Lien、Zoltan A. Tokes

  DOI：10.1021/jm00386a012

  日期：1987.3

  A series of 16 derivatives of 2-hydroxy-1H-isoindole-1,3-diones was designed and synthesized as potential antitumor agents. The cytostatic activity against L1210 cell growth of these compounds was studied, and their IC50 values were found to be in the range of 10(-4) to 10(-8) M. Quantitative structure-activity relationship analysis of these compounds showed that the inhibitory effect was well correlated with the electronic and the lipophilic parameters. Derivatives having a substituent with strongly electron-donating properties at the 6-position showed enhanced inhibitory activity while compounds having an electron-withdrawing group at the same position showed lower activity.
• 2-[(Alkylsulfonyl)oxy]-6-substituted-1H-isoindole-1,3(2H)-dione mechanism-based inhibitors of human leukocyte elastase
  作者：John E. Kerrigan、Jennifer J. Shirley

  DOI：10.1016/0960-894x(96)00038-8

  日期：1996.2

  Derivatives of 2-[(alkylsulfonyl)oxy]-1H-isoindole-1,3(2H)-diones (N-(sulfonyloxy)phthalimides) with ring substituents in the 6-position were found to exhibit enhanced inhibitory potency and selectivity for HLE. The most potent inhibitor of HLE in this series was 6-amino-2-[(methylsulfonyl)oxy]-1H-isoindole-1,3(2H)-dione 10 with a k(obs)/[I] of 110,000 M(-1) s(-1).