3,5-dimethyl-1H-pyrrole-2,4-dicarbohydrazide | 87781-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,5-dimethyl-1H-pyrrole-2,4-dicarbohydrazide
• 英文别名: 3,5-dimethyl-pyrrole-2,4-dicarboxylic acid dihydrazide；3,5-Dimethyl-pyrrol-2,4-dicarbonsaeure-dihydrazid
• CAS: 87781-09-7
• 化学式: C₈H₁₃N₅O₂
• 分子量: 211.224
• InChiKey: YYQGHTVYXOGTGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C(Solv: ethanol (64-17-5))
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  126
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-1H-pyrrole-2,4-dicarbohydrazide 在 溶剂黄146 、 sodium nitrite 作用下， 生成 3,5-dimethyl-pyrrole-2,4-dicarbonyl azide
  参考文献：
  名称：

  Fischer; Waibel, Justus Liebigs Annalen der Chemie, 1934, vol. 512, p. 195,209

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二甲基吡咯-3,5-二羧酸二乙酯 在 一水合肼 作用下， 反应 8.0h， 以75%的产率得到3,5-dimethyl-1H-pyrrole-2,4-dicarbohydrazide
  参考文献：
  名称：

  Bis-isatin hydrazones with novel linkers: Synthesis and biological evaluation as cytotoxic agents

  摘要：

  Many bis-isatins and isatins with hydrazide extension were reported to have a potential anti-proliferative effects against different cancer cell lines and cancer targets. In this study, four series of bis-isatins with hydrazide linkers were synthesized. These compounds were investigated for their antitumor activity by assessing their cytotoxic potency against HepG2, MCF-7 and HCT-116 cancer cell lines. Compound 21c possessed significant cytotoxic activity against MCF-7 (IC50 = 1.84 mu M) and HCT-116 (IC50 = 331 mu M) that surpasses the activity of doxorubicin against both cell lines (MCF-7; IC50 = 2.57 mu M and HCT-116; IC50 = 3.70 mu M). Cell cycle analysis and annexin V-FITC staining of MCF-7 cells treated with 21c suggested that the cytotoxic effect of the compound could be attributed to its pro-apoptotic activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.047

文献信息

• Fischer et al., Justus Liebigs Annalen der Chemie, 1930, vol. 481, p. 159,191
  作者：Fischer et al.

  DOI：——

  日期：——
• Bis-isatin hydrazones with novel linkers: Synthesis and biological evaluation as cytotoxic agents
  作者：Hany S. Ibrahim、Sahar M. Abou-seri、Nasser S.M. Ismail、Mahmoud M. Elaasser、Mohamed H. Aly、Hatem A. Abdel-Aziz

  DOI：10.1016/j.ejmech.2015.11.047

  日期：2016.1

  Many bis-isatins and isatins with hydrazide extension were reported to have a potential anti-proliferative effects against different cancer cell lines and cancer targets. In this study, four series of bis-isatins with hydrazide linkers were synthesized. These compounds were investigated for their antitumor activity by assessing their cytotoxic potency against HepG2, MCF-7 and HCT-116 cancer cell lines. Compound 21c possessed significant cytotoxic activity against MCF-7 (IC50 = 1.84 mu M) and HCT-116 (IC50 = 331 mu M) that surpasses the activity of doxorubicin against both cell lines (MCF-7; IC50 = 2.57 mu M and HCT-116; IC50 = 3.70 mu M). Cell cycle analysis and annexin V-FITC staining of MCF-7 cells treated with 21c suggested that the cytotoxic effect of the compound could be attributed to its pro-apoptotic activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Fischer; Waibel, Justus Liebigs Annalen der Chemie, 1934, vol. 512, p. 195,209
  作者：Fischer、Waibel

  DOI：——

  日期：——