Ethanesulfonic acid 5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl ester | 259253-00-4

• 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: Ethanesulfonic acid 5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl ester
• 英文别名: (5-Amino-1,3-dioxoisoindol-2-yl) ethanesulfonate
• CAS: 259253-00-4
• 化学式: C₁₀H₁₀N₂O₅S
• 分子量: 270.266
• InChiKey: ITZQUSWQDWRIEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  甲基戊酰氯 、 Ethanesulfonic acid 5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到Methyl 2-[(2-ethylsulfonyloxy-1,3-dioxoisoindol-5-yl)amino]-2-oxoacetate
  参考文献：
  名称：

  6-Acylamino-2-[(alkylsulfonyl)oxy]-1 H -isoindole-1,3-dione mechanism-based inhibitors of human leukocyte elastase

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00588-0
• 作为产物：
  描述：

  4-硝基邻苯二甲酸酐 在 palladium on activated charcoal 碳酸氢钠 、 三乙胺 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 生成 Ethanesulfonic acid 5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl ester
  参考文献：
  名称：

  6-acylamino-2-[(ethylsulfonyl)oxy]-1H-isoindole-1,3-diones mechanism-based inhibitors of human leukocyte elastase and cathepsin G: effect of chirality in the 6-acylamino substituent on inhibitory potency and selectivity

  摘要：

  Inhibition of human leukocyte elastase(HLE) by a series of 6-acylamino-2-[(ethylsulfonyl)oxy)]-1H-isoindole-1,3-diones was determined and compared to their inhibition of ChT, PPE, and Cat G. The best inhibitor of the series was 6-((1'S')-camphanyl)amino-2-[(ethylsulfonyl) oxy]-1H-isoindole-1,3-dione 5b, with a k(obs)/[I] = 11,000 M-1 s(-1). this study revealed that HLE shows a preference for the S stereochemistry and tolerates hydrophobic substituents in the S-n(') binding sites. Molecular modeling of non-covalent HLE-inhibitor complexes was used as a tool to investigate our binding model. Buffer stability assays reveal that these compounds are susceptible to hydrolysis at physiological pH. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00281-9

文献信息

• 6-acylamino-2-[(ethylsulfonyl)oxy]-1H-isoindole-1,3-diones mechanism-based inhibitors of human leukocyte elastase and cathepsin G: effect of chirality in the 6-acylamino substituent on inhibitory potency and selectivity
  作者：Lisa M. Vagnoni、Michael Gronostaj、John E. Kerrigan

  DOI：10.1016/s0968-0896(00)00281-9

  日期：2001.3

  Inhibition of human leukocyte elastase(HLE) by a series of 6-acylamino-2-[(ethylsulfonyl)oxy)]-1H-isoindole-1,3-diones was determined and compared to their inhibition of ChT, PPE, and Cat G. The best inhibitor of the series was 6-((1'S')-camphanyl)amino-2-[(ethylsulfonyl) oxy]-1H-isoindole-1,3-dione 5b, with a k(obs)/[I] = 11,000 M-1 s(-1). this study revealed that HLE shows a preference for the S stereochemistry and tolerates hydrophobic substituents in the S-n(') binding sites. Molecular modeling of non-covalent HLE-inhibitor complexes was used as a tool to investigate our binding model. Buffer stability assays reveal that these compounds are susceptible to hydrolysis at physiological pH. (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.