3-hydrazinylidene-1-propylindol-2-one | 726151-82-2

• 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: 3-hydrazinylidene-1-propylindol-2-one
• CAS: 726151-82-2
• 化学式: C₁₁H₁₃N₃O
• 分子量: 203.244
• InChiKey: ZEDJVEJVFZMZLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-hydrazinylidene-1-propylindol-2-one 在 lithium acetate 、 Selectfluor 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以69%的产率得到3-fluoro-1-propylindolin-2-one
  参考文献：
  名称：

  Solvent Effects: Syntheses of 3,3-Difluorooxindoles and 3-Fluorooxindoles from Hydrazonoindolin-2-one by Selectfluor

  摘要：

  Efficient syntheses of 3,3-difluorooxindoles and 3-fluorooxindoles via fluorination of hydrazonoindolin-2-one with Selectfluor are reported. Under different solvent conditions, this method produced 3,3-difluorooxindoles and 3-fluorooxindoles selectively. The broad substrate scope and mild reaction conditions make this transformation a valuable method in drug discovery and development.

  DOI：

  10.1021/acs.joc.8b00737
• 作为产物：
  描述：

  1-丙基-1H-吲哚-2,3-二酮 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-hydrazinylidene-1-propylindol-2-one
  参考文献：
  名称：

  Novel [(3-indolylmethylene)hydrazono]indolin-2-ones as apoptotic anti-proliferative agents: design, synthesis andin vitrobiological evaluation

  摘要：

  On account of their significance as apoptosis inducing agents, merging indole and 3-hydrazinoindolin-2-one scaffolds is a logic tactic for designing pro-apoptotic agents. Consequently, 27 hybrids (6a-r, 9a-f and 11a-c) were synthesised and evaluated for their cytotoxicity against MCF-7, HepG-2 and HCT-116 cancer cell lines. SAR studies unravelled that N-propylindole derivatives were the most active compounds such as 6n (MCF-7; IC50=1.04 mu M), which displayed a significant decrease of cell population in the G2/M phase and significant increase in the early and late apoptosis by 19-folds in Annexin-V-FTIC assay. Also, 6n increased the expression of caspase-3, caspase-9, cytochrome C and Bax and decreased the expression of Bcl-2. Moreover, compounds 6i, 6j, 6n and 6q generated ROS by significant increase in the level of SOD and depletion of the levels of CAT and GSH-Px in MCF-7.

  DOI：

  10.1080/14756366.2017.1421181

文献信息

• New chromogenic bis(isatin hydrazonyl)calix[4]arenes for dual recognition of fluoride and silver ions
  作者：Har Mohindra Chawla、Tanu Gupta

  DOI：10.1016/j.tetlet.2013.01.038

  日期：2013.4

  New calixarene based dual chromogenic receptors bearing isatin hydrazone units have been synthesized and evaluated for their ion recognition potential. The synthesized molecular receptors can effectively and selectively recognize fluoride and silver ions through visible color changes and pronounced bathochromic shifts in their UV-visible spectra. NMR titration data further support the preliminary conclusions. (C) 2013 Elsevier Ltd. All rights reserved.
• Solvent Effects: Syntheses of 3,3-Difluorooxindoles and 3-Fluorooxindoles from Hydrazonoindolin-2-one by Selectfluor
  作者：Qiong Yang、Guo-Li Dai、Yu-Ming Yang、Zhuangzhu Luo、Zhen-Yu Tang

  DOI：10.1021/acs.joc.8b00737

  日期：2018.6.15

  Efficient syntheses of 3,3-difluorooxindoles and 3-fluorooxindoles via fluorination of hydrazonoindolin-2-one with Selectfluor are reported. Under different solvent conditions, this method produced 3,3-difluorooxindoles and 3-fluorooxindoles selectively. The broad substrate scope and mild reaction conditions make this transformation a valuable method in drug discovery and development.
• Novel [(3-indolylmethylene)hydrazono]indolin-2-ones as apoptotic anti-proliferative agents: design, synthesis and<i>in vitro</i>biological evaluation
  作者：Wagdy M. Eldehna、Mahmoud F. Abo-Ashour、Hany S. Ibrahim、Ghada H. Al-Ansary、Hazem A. Ghabbour、Mahmoud M. Elaasser、Hanaa Y. A. Ahmed、Nesreen A. Safwat

  DOI：10.1080/14756366.2017.1421181

  日期：2018.1.1

  On account of their significance as apoptosis inducing agents, merging indole and 3-hydrazinoindolin-2-one scaffolds is a logic tactic for designing pro-apoptotic agents. Consequently, 27 hybrids (6a-r, 9a-f and 11a-c) were synthesised and evaluated for their cytotoxicity against MCF-7, HepG-2 and HCT-116 cancer cell lines. SAR studies unravelled that N-propylindole derivatives were the most active compounds such as 6n (MCF-7; IC50=1.04 mu M), which displayed a significant decrease of cell population in the G2/M phase and significant increase in the early and late apoptosis by 19-folds in Annexin-V-FTIC assay. Also, 6n increased the expression of caspase-3, caspase-9, cytochrome C and Bax and decreased the expression of Bcl-2. Moreover, compounds 6i, 6j, 6n and 6q generated ROS by significant increase in the level of SOD and depletion of the levels of CAT and GSH-Px in MCF-7.