N-(3,5-difluorophenyl)-2-(5-fluoro-2-oxo-1,2-dihydro-3Hindol-3-ylidene)-1-hydrazinecarbothioamide

• 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: N-(3,5-difluorophenyl)-2-(5-fluoro-2-oxo-1,2-dihydro-3Hindol-3-ylidene)-1-hydrazinecarbothioamide
• 英文别名: 1-(3,5-difluorophenyl)-3-[(5-fluoro-2-oxoindol-3-yl)amino]thiourea
• 化学式: C₁₅H₉F₃N₄OS
• 分子量: 350.324
• InChiKey: AKQXNUCQYMXXPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.52
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-氟靛红 、 4-(3,5-difluoro-phenyl)thiosemicarbazide 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以77%的产率得到N-(3,5-difluorophenyl)-2-(5-fluoro-2-oxo-1,2-dihydro-3Hindol-3-ylidene)-1-hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and biological evaluation of some N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones

  摘要：

  A series of N (4)-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones 3a-3l was synthesized and evaluated for selected biological activities. The brine shrimp lethality bioassay was carried out to study their in vitro cytotoxicity potential and besides, their antifungal, phytotoxic and urease inhibitory effects were also investigated. Seven compounds i.e. 3a, 3d, 3f, 3g, 3h, 3j and 3k proved to be active in the brine shrimp assay, displaying promising cytotoxicity (LD50 = 6.89 x 10(-5)-2.79 x 10(-4) M). Amongst these, 3a and 3h were found to be the most active ones (LD50 = 6.89 x 10(-5) and 9.79 x 10(-5) M, respectively). Compounds 3i, 3j and 3 k displayed moderate (40 %) antifungal activity against one or two fungal strains i.e. A. flavus and/or M. canis. In phytotoxicity assay, all the synthesized compounds, including the reference point 2m showed weak-to-moderate (15-70 %) activity at the highest tested concentration (500 mu g/mL). In urease inhibition assay, compounds 3f, 3g and 3j proved to be the most potent inhibitors, demonstrating relatively a higher degree of enzymatic inhibition with IC50 values ranging from 37.7 to 47.3 mu M.

  DOI：

  10.1007/s00044-013-0575-7

文献信息

• Synthesis and biological evaluation of some N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones
  作者：Humayun Pervez、Naveeda Saira、Mohammad Saeed Iqbal、Muhammad Yaqub、Khalid Mohammed Khan

  DOI：10.1007/s00044-013-0575-7

  日期：2013.12

  A series of N (4)-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones 3a-3l was synthesized and evaluated for selected biological activities. The brine shrimp lethality bioassay was carried out to study their in vitro cytotoxicity potential and besides, their antifungal, phytotoxic and urease inhibitory effects were also investigated. Seven compounds i.e. 3a, 3d, 3f, 3g, 3h, 3j and 3k proved to be active in the brine shrimp assay, displaying promising cytotoxicity (LD50 = 6.89 x 10(-5)-2.79 x 10(-4) M). Amongst these, 3a and 3h were found to be the most active ones (LD50 = 6.89 x 10(-5) and 9.79 x 10(-5) M, respectively). Compounds 3i, 3j and 3 k displayed moderate (40 %) antifungal activity against one or two fungal strains i.e. A. flavus and/or M. canis. In phytotoxicity assay, all the synthesized compounds, including the reference point 2m showed weak-to-moderate (15-70 %) activity at the highest tested concentration (500 mu g/mL). In urease inhibition assay, compounds 3f, 3g and 3j proved to be the most potent inhibitors, demonstrating relatively a higher degree of enzymatic inhibition with IC50 values ranging from 37.7 to 47.3 mu M.