2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonic acid 4-chlrobenzylamide | 953029-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonic acid 4-chlrobenzylamide
• 英文别名: 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonic acid 4-chlorobenzylamide；N-[(4-chlorophenyl)methyl]-2,3-dioxo-1H-indole-5-sulfonamide
• CAS: 953029-02-2
• 化学式: C₁₅H₁₁ClN₂O₄S
• 分子量: 350.782
• InChiKey: KCWKVIFLOWDBHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonic acid 4-chlrobenzylamide 、 2-硝基苯肼 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以43%的产率得到3-[(2-nitrophenyl)hydrazono]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid 4-chlorobenzylamide
  参考文献：
  名称：

  Inhibitors of Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (Shp2) Based on Oxindole Scaffolds

  摘要：

  Screening of the NCl diversity set of compounds has led to the identification of 5 (NSC-117199), which inhibits the protein tyrosine phosphatase (PTP) Shp2 with an IC(50) of 47 mu M. A focused library incorporating an isatin scaffold was designed and evaluated for inhibition of Shp2 and Shp1 PTP activities. Several compounds were identified that selectively inhibit Shp2 over ShpI and PTP1B with low to submicromolar activity. A model for the binding of the active compounds is proposed.

  DOI：

  10.1021/jm8002526
• 作为产物：
  描述：

  靛红 在 chloro sulfite 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonic acid 4-chlrobenzylamide
  参考文献：
  名称：

  含有磺酰胺基序的 3-羟基-2-羟吲哚衍生物：合成、抗病毒活性和作用方式

  摘要：

  3-羟基-2-羟吲哚基序构成了许多天然产物的核心结构，并赋予显着的生物活性。在这里，我们描述了四个系列的新型含磺酰胺部分的3-取代-3-羟基-2-羟吲哚衍生物的设计和合成及其对马铃薯Y病毒（PVY）的抗病毒活性。与先导化合物和市售宁南霉素相比，化合物10b在治疗和保护作用方面表现出最佳的抗病毒活性和优异的抗PVY活性。此外， 10b显着抑制本塞姆氏烟草中的 PVY 全身感染。生理和生化分析表明，经过10b处理后，烟草植物中四种重要的防御相关酶的活性有所增加。 RNA测序分析显示， 10b显着诱导了38个差异表达基因的上调，这些基因在光合作用途径中富集。这些发现表明10b是一种很有前途的抗病毒农用化学品，可以有效控制PVY感染并触发植物宿主免疫以产生病毒抗性。这项研究为开发新农药提供了新的分子实体和思路。

  DOI：

  10.1021/acs.jafc.2c06881

文献信息

• Inhibition of Shp2/PTPN11 Protein Tyrosine Phosphatase by NSC-87877, NSC-117199 and Their Analogs
  申请人：Wu Jie

  公开号：US20080176309A1

  公开（公告）日：2008-07-24

  Compounds and associated methods for inhibiting a protein tyrosine phosphatase. By a combination of experimental and virtual screenings of the NCI Diversity Set chemical library, NSC-87877 and NSC-117199 have been identified as Shp2 PTP inhibitors. Significantly, NSC-87877 is active in cell-based assays and has no detectable off-target effects in the EGF-stimulated Erk1/2 activation pathway. Additionally, a number of analogs of NSC-117199 have been produced. These analogs exhibit enhanced protein tyrosine phosphatase inhibition and are found to be potent and/or selective inhibitors of Shp1 and/or Shp2 protein tyrosine phosphatases.

  化合物及其相关方法，用于抑制蛋白酪氨酸磷酸酶。通过NCI Diversity Set化学库的实验和虚拟筛选的组合，已经确定NSC-87877和NSC-117199是Shp2 PTP抑制剂。值得注意的是，NSC-87877在基于细胞的实验中是活性的，并且在EGF刺激的Erk1/2激活途径中没有检测到任何非靶效应。此外，已经生产了许多NSC-117199的类似物。这些类似物表现出增强的蛋白酪氨酸磷酸酶抑制作用，并被发现是Shp1和/或Shp2蛋白酪氨酸磷酸酶的有效和/或选择性抑制剂。
• US8987474B2
  申请人：——

  公开号：US8987474B2

  公开（公告）日：2015-03-24
• [EN] INHIBITION OF SHP2/PTPN11 PROTEIN TYROSINE PHOSPHATASE BY NSC-117199 AND ANALOGS<br/>[FR] INHIBITION DE LA PROTÉINE TYROSINE PHOSPHATASE SHP2/PTPN11 PAR NSC-117199 ET ANALOGUES
  申请人：H LEE MOFFITT CANCER CT AND RE

  公开号：WO2009135000A2

  公开（公告）日：2009-11-05

  Protein tyrosine phosphatase (PTP) Shp2 is a non-receptor PTP that involved in cell signaling and regulation of cell proliferation, differentiation, and migration. Shp2 mediates activation of kinases that are involved in the pathogenesis of human carcinoma. NSC-117199 was identified as a porent inhibitor of the protein tyrosine phosphatase (PTPa) Shp2. A focused library of analogs incorporating an isatin scaffold was designed and evaluated for inhibition of Shp2 and Shp1 PTP activities. Several compounds were identified that selectively inhibit Shp2 over Shp1 and PTP1B with low to sub-micromolar activity. Also disclosed are methods of inhibiting a protein tyrosine phosphatase in a cell and treating cancer through selective inhibition of Shp2.
• Inhibitors of Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (Shp2) Based on Oxindole Scaffolds
  作者：Harshani R. Lawrence、Roberta Pireddu、Liwei Chen、Yunting Luo、Shen-Shu Sung、Ann Marie Szymanski、M. L. Richard Yip、Wayne C. Guida、Saïd M. Sebti、Jie Wu、Nicholas J. Lawrence

  DOI：10.1021/jm8002526

  日期：2008.8.1

  Screening of the NCl diversity set of compounds has led to the identification of 5 (NSC-117199), which inhibits the protein tyrosine phosphatase (PTP) Shp2 with an IC(50) of 47 mu M. A focused library incorporating an isatin scaffold was designed and evaluated for inhibition of Shp2 and Shp1 PTP activities. Several compounds were identified that selectively inhibit Shp2 over ShpI and PTP1B with low to submicromolar activity. A model for the binding of the active compounds is proposed.
• 3-Hydroxy-2-oxindole Derivatives Containing Sulfonamide Motif: Synthesis, Antiviral Activity, and Modes of Action
  作者：Chunle Wei、Xiong Yang、Shaojie Shi、Lian Bai、Deyu Hu、Runjiang Song、Baoan Song

  DOI：10.1021/acs.jafc.2c06881

  日期：2023.1.11

  Nicotiana benthamiana. Physiological and biochemical analyses revealed that the activities of the four crucial defense-related enzymes increased in the tobacco plant following treatment with 10b. RNA-sequencing analysis revealed that 10b substantially induced the upregulation of 38 differentially expressed genes, which were enriched in the photosynthesis pathway. These findings suggest that 10b is a promising

  3-羟基-2-羟吲哚基序构成了许多天然产物的核心结构，并赋予显着的生物活性。在这里，我们描述了四个系列的新型含磺酰胺部分的3-取代-3-羟基-2-羟吲哚衍生物的设计和合成及其对马铃薯Y病毒（PVY）的抗病毒活性。与先导化合物和市售宁南霉素相比，化合物10b在治疗和保护作用方面表现出最佳的抗病毒活性和优异的抗PVY活性。此外， 10b显着抑制本塞姆氏烟草中的 PVY 全身感染。生理和生化分析表明，经过10b处理后，烟草植物中四种重要的防御相关酶的活性有所增加。 RNA测序分析显示， 10b显着诱导了38个差异表达基因的上调，这些基因在光合作用途径中富集。这些发现表明10b是一种很有前途的抗病毒农用化学品，可以有效控制PVY感染并触发植物宿主免疫以产生病毒抗性。这项研究为开发新农药提供了新的分子实体和思路。