3-[2-(2-nitrophenyl)hydrazinyl]indol-2-one | 20096-35-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[2-(2-nitrophenyl)hydrazinyl]indol-2-one
• CAS: 20096-35-9；144405-88-9；1051388-01-2
• 化学式: C₁₄H₁₀N₄O₃
• 分子量: 282.258
• InChiKey: IDXLIYHMYGCOKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  靛红 、 2-硝基苯肼 以 乙醇 为溶剂， 反应 1.0h， 生成 3-[2-(2-nitrophenyl)hydrazinyl]indol-2-one
  参考文献：
  名称：

  潜在的抗惊厥药。九。一些伊斯汀和相关化合物

  摘要：

  许多肼，酰肼和相关化合物已与Isatin和取代的Isatin缩合。报道了这些化合物的抗惊厥活性。

  DOI：

  10.1002/jhet.5570210614

文献信息

• Potential anticonvulsants. IX. Some isatin hydrazones and related compounds
  作者：Frank D. Popp

  DOI：10.1002/jhet.5570210614

  日期：1984.11

  A number of hydrazines, hydrazides, and related compounds have been condensed with isatin and substituted isatins. The anticonvulsant activity of these compounds is reported.

  许多肼，酰肼和相关化合物已与Isatin和取代的Isatin缩合。报道了这些化合物的抗惊厥活性。
• Effect of a =X-NH-Fragment, (X = C, N), on Z/E Isomerization and ON/OFF Functionality of Isatin Arylhydrazones, ((Arylamino)Methylene)Indolin-2-Ones and Their Anions
  作者：Pavol Tisovský、Klaudia Csicsai、Jana Donovalová、Róbert Šandrik、Róbert Sokolík、Anton Gáplovský

  DOI：10.3390/molecules25133082

  日期：——

  The subject of this work was the study of thermally and photochemically stimulated Z ↔ E isomerization and hydrazo ↔ azo tautomerism of Z- and E-isomers of isatin arylhydrazones and ((arylamino)methylene)indolin-2-ones and their anions. Using NMR, UV-Vis spectroscopy, kinetic measurements, and HPLC, we studied the relationship of structure, (Z- and E-isomers), of these compounds and hydrazo=azo tautomerism

  这项工作的主题是研究靛红芳基腙和 ((芳氨基) 亚甲基) indolin-2-ones 及其阴离子的 Z ↔ E 异构化和 hydrazo ↔ 偶氮互变异构体的热和光化学刺激。使用 NMR、UV-Vis 光谱、动力学测量和 HPLC，我们研究了这些化合物的结构（Z-和 E-异构体）与 hydrazo=azo 互变异构的关系。研究了这些化合物及其阴离子的开/关功能，使用光来刺激开和关状态之间的切换。我们指出了 =N- 和 =CH- 结构片段和芳基结构对靛红芳基腙和 ((芳基氨基) 亚甲基) indolin-2-ones 的 ON 和 OFF 状态的影响的表征。
• 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。
• Hydrazone derivatives, their preparation and use
  申请人：NEUROSEARCH A/S

  公开号：EP0503349A1

  公开（公告）日：1992-09-16

  A method of treatment with compounds having the formula wherein n is 0 or 1; R¹ is hydrogen, C₁₋₆-alkyl which may be branched, C₃₋₇-cycloalkyl, benzyl, phenyl which may be substituted, acyl, hydroxy, C₁₋₆-alkoxy, CH₂CO₂R' wherein R' is hydrogen or C₁₋₆-alkyl which may be branched, CH₂CN, CH₂CONRIVRV wherein RIV and RV independently are hydrogen or C₁₋₆-alkyl, or CH₂C(=NOH)NH₂; R² is pyridyl or phenyl, both of which may be substituted one or more times preferably in the ortho and para positions with halogen, CF₃, NO₂, CN, phenyl, SO₂NR''R''' wherein R'' and R''' independently are hydrogen, benzyl, or C₁₋₆-alkyl; R⁴, R⁵, R⁶, R⁷ independently are hydrogen, C₁₋₆-alkyl which may be branched, phenyl, halogen, C₁₋₆-alkoxy, NO₂, CN, CF₃, or SO₂NR¹¹R¹² wherein R¹¹ and R¹² independently are hydrogen, benzyl, or C₁₋₆-alkyl; or R⁶ and R⁷ together form an additional 4 to 8 membered carbocyclic ring which may be aromatic or partial saturated and which may be substituted with halogen, NO₂, CF₃, CN, SO₂NR¹³R¹⁴ wherein R¹³ and R¹⁴ independently are hydrogen, benzyl, or C₁₋₆-alkyl, and R⁴ and R⁵ have the meanings set forth above; or R⁴ and R⁵ together form an additional 4 to 8 membered carbocyclic ring which may be aromatic or partial saturated and which may be substituted with halogen, NO₂, CF₃, CN, SO₂NR¹³R¹⁴ wherein R¹³ and R¹⁴ independently are hydrogen, benzyl, or C₁₋₆-alkyl, and R⁶ and R⁷ have the meanings set forth above. Certain of the compounds are novel. The compounds and pharmaceutical compositions containing the compounds are useful in the treatment of central nervous system disorders and especially conditions sensitive to excitatory amino acids.

  一种用具有以下式子的化合物进行处理的方法 其中 n 是 0 或 1； R¹ 是氢、C₁₋₆-烷基（可为支链）、C₃₋₇-环烷基、苄基、苯基（可被取代）、 酰基、羟基、C₁₋₆-烷氧基、CH₂CO₂R'（其中 R'为氢或 C₁₋₆- 烷基，可为支链）、CH₂CN、CH₂CONRIVRV（其中 RIV 和 RV 独立地为氢或 C₁₋₆-烷基）或 CH₂C(=NOH)NH₂； R² 是吡啶基或苯基，二者最好在正位和对位被卤素、CF₃、NO₂、CN、苯基、SO₂NR''R'''取代一次或多次，其中 R'' 和 R'''' 独立地为氢、苄基或 C₁₋₆-烷基； R⁴、R⁵、R⁶、R⁷ 各自为氢、C₁₋₆-烷基（可为支链）、苯基、卤素、C₁₋₆-烷氧基、NO₂、CN、CF₃或 SO₂NR¹R¹²，其中 R¹ 和 R¹² 独立地是氢、苄基或 C₁₋₆-烷基；或 R⁶ 和 R⁷ 共同形成另外一个 4 至 8 个成员的碳环，该碳环可为芳香族或部分饱和环，可被卤素、NO₂、CF₃、CN、SO₂NR¹³R¹⁴，其中 R¹³ 和 R¹⁴ 独立为氢、苄基或 C₁₋₆ 烷基，且 R⁴ 和 R⁵ 具有上述含义； 或 R⁴ 和 R⁵ 共同形成一个额外的 4 至 8 位碳环，该碳环可为芳香族或部分饱和环，可被卤素、NO₂、CF₃、CN、SO₂NR¹³R¹⁴，其中 R¹³ 和 R¹⁴ 独立地为氢、苄基或 C₁₋₆ 烷基，且 R⁶ 和 R⁷ 具有上述含义。 某些化合物具有新颖性。 这些化合物和含有这些化合物的药物组合物可用于治疗中枢神经系统疾病，特别是对兴奋性氨基酸敏感的疾病。
• 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.