(Z)-N’-(4-chloro-2-oxoindolin-3-ylidene)-4-phenylpiperazine-1-carbothiohydrazide | 1396785-95-7

• 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: (Z)-N’-(4-chloro-2-oxoindolin-3-ylidene)-4-phenylpiperazine-1-carbothiohydrazide
• 英文别名: N'-(4-chloro-2-oxoindol-3-yl)-4-phenylpiperazine-1-carbothiohydrazide
• CAS: 1396785-95-7；1435909-53-7
• 化学式: C₁₉H₁₈ClN₅OS
• 分子量: 399.904
• InChiKey: WLMQKIXKHATAIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59.97
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-苯基哌嗪 在 甲醇 、 乙醇 作用下， 反应 20.0h， 生成 (Z)-N’-(4-chloro-2-oxoindolin-3-ylidene)-4-phenylpiperazine-1-carbothiohydrazide
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of piperazine-1-carbothiohydrazide derivatives of indolin-2-one

  摘要：

  By varying the substituents (R-1) at the indolin-2-one scaffold, a series of indolin-2-one derivatives bearing 4-phenylpiperazine-1-carbothiohydrazide moiety at the C3-position were synthesized and evaluated for their antiproliferative activity against three human cancer cell lines. We further selected the 5-chloroindolin-2-one moiety for the extension to another series of compounds by varying the substituents (R-2) at the phenyl group connected with the piperazine ring. Among all the compounds synthesized, 6d and 6l were most potent with IC50 values of 3.59 and 5.58 mu M, respectively against A549 lung cancer cells, while 5f and 6l possessed IC50 values of 3.49 and 4.57 mu M, respectively against HCT-116 colon cancer cells which were comparable to that of Sunitinib, an indolin-2-one derivative in cancer therapy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.099

文献信息

• Synthesis and antiproliferative evaluation of piperazine-1-carbothiohydrazide derivatives of indolin-2-one
  作者：Hui-Hui Lin、Wei-Yao Wu、Sheng-Li Cao、Ji Liao、Li Ma、Man Gao、Zhong-Feng Li、Xingzhi Xu

  DOI：10.1016/j.bmcl.2013.03.099

  日期：2013.6

  By varying the substituents (R-1) at the indolin-2-one scaffold, a series of indolin-2-one derivatives bearing 4-phenylpiperazine-1-carbothiohydrazide moiety at the C3-position were synthesized and evaluated for their antiproliferative activity against three human cancer cell lines. We further selected the 5-chloroindolin-2-one moiety for the extension to another series of compounds by varying the substituents (R-2) at the phenyl group connected with the piperazine ring. Among all the compounds synthesized, 6d and 6l were most potent with IC50 values of 3.59 and 5.58 mu M, respectively against A549 lung cancer cells, while 5f and 6l possessed IC50 values of 3.49 and 4.57 mu M, respectively against HCT-116 colon cancer cells which were comparable to that of Sunitinib, an indolin-2-one derivative in cancer therapy. (C) 2013 Elsevier Ltd. All rights reserved.