1-[(4-phenyl-1-piperazinyl)methyl]-1H-indole-2,3-dione | 6532-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-[(4-phenyl-1-piperazinyl)methyl]-1H-indole-2,3-dione
• 英文别名: 1-({4-phenylpiperazin-1-yl}methyl)indoline-2,3-dione；1-[(4-phenylpiperazin-1-yl)methyl]-1H-indole-2,3-dione；1-[(4-phenylpiperazin-1-yl)methyl]indole-2,3-dione
• CAS: 6532-18-9
• 化学式: C₁₉H₁₉N₃O₂
• mdl: MFCD00390595
• 分子量: 321.379
• InChiKey: PXUXTGVNHPHAHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  212-213 °C
• 沸点：
  503.9±60.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-2-噻唑啉 、 1-[(4-phenyl-1-piperazinyl)methyl]-1H-indole-2,3-dione 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以60%的产率得到3-(4,5-dihydro[1,3]thiazol-2-ylimino)-1-[(4-phenylpiperazin-1-yl)methyl]indol-2(3H)-one
  参考文献：
  名称：

  Synthesis of novel isatin-thiazoline and isatin-benzimidazole conjugates as anti-breast cancer agents

  摘要：

  一系列新的靛红-噻唑啉3a–h和靛红-苯并咪唑4a–h衍生物通过靛红Mannich碱2a–h与2-氨基噻唑啉或2-氨基苯并咪唑的缩合反应合成。新合成化合物的结构通过光谱数据进行了表征。评估了部分合成化合物在MCF-7人类乳腺癌细胞系中的抗乳腺癌活性。结果显示，化合物4b、4d和4g对MCF-7细胞具有显著的抗增殖活性。

  DOI：

  10.1007/s12272-011-1005-3
• 作为产物：
  描述：

  聚合甲醛 、 N-苯基哌嗪 、 靛红 以 乙醇 为溶剂， 反应 6.0h， 生成 1-[(4-phenyl-1-piperazinyl)methyl]-1H-indole-2,3-dione
  参考文献：
  名称：

  Synthesis of novel isatin-thiazoline and isatin-benzimidazole conjugates as anti-breast cancer agents

  摘要：

  一系列新的靛红-噻唑啉3a–h和靛红-苯并咪唑4a–h衍生物通过靛红Mannich碱2a–h与2-氨基噻唑啉或2-氨基苯并咪唑的缩合反应合成。新合成化合物的结构通过光谱数据进行了表征。评估了部分合成化合物在MCF-7人类乳腺癌细胞系中的抗乳腺癌活性。结果显示，化合物4b、4d和4g对MCF-7细胞具有显著的抗增殖活性。

  DOI：

  10.1007/s12272-011-1005-3

文献信息

• A Study on Hydrolytic Stability of Isatin N-Mannich Bases
  作者：D. D. Orlova、D. S. Novikova、A. V. Garabadzhiu、V. G. Tribulovich

  DOI：10.1134/s1070363218010085

  日期：2018.1

  Stability parameters of biologically active compounds with N-Mannich base motif in their structure, which is susceptible to hydrolysis, have been studied. A procedure for the synthesis of small molecule compounds reactivating the function of the p53 tumor suppressor protein was developed, and the dependence of the Mannich base degradation rate on the structure of the compounds was established. For the hydrolysis reaction we determined the rate constants and calculated rho, Delta G#, Delta H, and Delta S. Modifications of active compounds that retain the activity at the maximum possible stability were proposed.
• Discovery of Novel Isatin-Based p53 Inducers
  作者：P. Davidovich、V. Aksenova、V. Petrova、D. Tentler、D. Orlova、S. Smirnov、V. Gurzhiy、A. L. Okorokov、A. Garabadzhiu、G. Melino、N. Barlev、V. Tribulovich

  DOI：10.1021/acsmedchemlett.5b00011

  日期：2015.8.13

  A series of isatin Schiff base derivatives were identified during in silk screening of the small molecule library for novel activators of p53. The compounds selected based on molecular docking results were further validated by a high-content screening assay using U2OS human osteosarcoma cells with an integrated EGFP-expressing p53-dependent reporter. The hit compounds activated and stabilized p53, as shown by Western blotting, at higher rates than the well-known positive control Nutlin-3. Thus, the p53-activating compounds identified by this approach represent useful molecular probes for various cancer studies.
• RADUL O. M.; ZHUNGIETU G. I., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1976, HO 9, 1211-1214
  作者：RADUL O. M.、 ZHUNGIETU G. I.

  DOI：——

  日期：——