(4-(三氟甲氧基)苯基)氨基二硫代甲酸 | 846062-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (4-(三氟甲氧基)苯基)氨基二硫代甲酸
• 英文名称: [4-(Trifluoromethoxy)phenyl]carbamodithioic acid
• 英文别名: [4-(trifluoromethoxy)phenyl]carbamodithioic acid
• CAS: 846062-12-2
• 化学式: C₈H₆F₃NOS₂
• 分子量: 253.269
• InChiKey: QXKQWFDVAWDXAB-UHFFFAOYSA-N

物化性质

• 沸点：
  256.7±50.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-(三氟甲氧基)苯基)氨基二硫代甲酸 在 均苯三甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-benzyl-4-(3-(3-(4-(trifluoromethoxy)phenyl)thioureido)phenoxy)picolinamide
  参考文献：
  名称：

  Design, synthesis and biological activities of sorafenib derivatives as antitumor agents

  摘要：

  A series of novel sorafenib derivatives, 9a-w, was designed and synthesized in high yields using various substituted anilines, and their antiproliferative activities against HCT116, PC-3 and MDA-MB-231 cell lines were also evaluated and described. All compounds exhibited potent antiproliferative activity against HCT116 and PC-3 cells with IC50 = 2.8-52.0 and 2.2-45.6 mu M; compounds 9p and 9q demonstrated competitive antiproliferative activities to sorafenib against all three cancer cell lines, the cytotoxicity of compound 9r is more potent than that of sorafenib. Compounds (9g, 9p, 9q and 9r) were chosen for further evaluation of the anti-angiogenesis activity, and showed the inhibition of sprout formation from aortic ring ex vivo. The structures of all the newly synthesized compounds were determined by H-1 NMR, C-13 NMR and HRMS. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.031
• 作为产物：
  描述：

  二硫化碳 、 对三氟甲氧基苯胺 在 三乙烯二胺 作用下， 以 甲苯 为溶剂， 生成 (4-(三氟甲氧基)苯基)氨基二硫代甲酸
  参考文献：
  名称：

  二芳基硫脲衍生物作为抗癌剂的设计，合成及抗增殖活性

  摘要：

  设计并合成了两个新的含索拉非尼衍生物9a - 9t的二芳基硫脲系列产品，并评估了它们对PC-3，HCT116和MDA-MB-231细胞系的抗增殖活性。所有化合物通常对PC-3细胞均具有抗增殖活性，大多数类似物均对HCT116细胞具有有效的抗增殖活性，化合物9e，9f，9o和9p对所有这三种细胞系均具有抑制活性。所有新合成的化合物的结构均通过1 H NMR，13 C NMR和HRMS确定。

  DOI：

  10.1002/cjoc.201200708

文献信息

• Design, synthesis and biological evaluation of thiourea and nicotinamide-containing sorafenib analogs as antitumor agents
  作者：Xiangkai Kong、Zeyu Yao、Zuopeng He、Wenfang Xu、Jianwen Yao

  DOI：10.1039/c4md00536h

  日期：——

  Thiourea and nicotinamide-containing sorafenib analogs with better antiproliferative and anti-angiogenic activities than sorafenib were well designed and synthesized.

  硫脲和烟酰胺含量比索拉非尼更好的抗增殖和抗血管生成活性的类索拉非尼类似物已经被设计和合成。
• Thiourea and thioether derivatives of sorafenib: synthesis, crystal structure, and antiproliferative activity
  作者：Jianwen Yao、Jing Chen、Zuopeng He、Wei Sun、Hao Fang、Wenfang Xu

  DOI：10.1007/s00044-012-0400-8

  日期：2013.8

  A series of novel sorafenib derivatives containing diaryl thiourea and thioether, 9a-u, was designed and synthesized, and their antiproliferative activities against HCT116 and MDA-MB-231 cell lines were also evaluated and described. Most compounds exhibited potent antiproliferative activity against HCT116 cells with IC50 = 1.8-80.4 mu M. Compounds 9p, 9r, and 9s demonstrated competitive antiproliferative activities to sorafenib, against all two cancer cell lines. The structures of all the newly synthesized compounds were determined by H-1 NMR, C-13 NMR, and HRMS, and compound 9n was characterized by single-crystal X-ray diffraction. Primary structure-activity relationships (SAR) have also been established.
• Design, Synthesis and Antiproliferative Activities of Diaryl Thiourea Derivatives as Anticancer Agents
  作者：Jianwen Yao、Zuopeng He、Jing Chen、Daquan Chen、Wei Sun、Wenfang Xu

  DOI：10.1002/cjoc.201200708

  日期：2012.10

  Two new series of diaryl thiourea containing sorafenib derivatives 9a–9t were designed and synthesized, and their antiproliferative activities against PC‐3, HCT116 and MDA‐MB‐231 cell lines were evaluated. All compounds generally showed antiproliferative activity to PC‐3 cells, most of the analogs exhibited potent antiproliferative activity to HCT116 cells, and compounds 9e, 9f, 9o and 9p demonstrated

  设计并合成了两个新的含索拉非尼衍生物9a - 9t的二芳基硫脲系列产品，并评估了它们对PC-3，HCT116和MDA-MB-231细胞系的抗增殖活性。所有化合物通常对PC-3细胞均具有抗增殖活性，大多数类似物均对HCT116细胞具有有效的抗增殖活性，化合物9e，9f，9o和9p对所有这三种细胞系均具有抑制活性。所有新合成的化合物的结构均通过1 H NMR，13 C NMR和HRMS确定。
• Design, synthesis and biological activities of sorafenib derivatives as antitumor agents
  作者：Jianwen Yao、Zuopeng He、Jing Chen、Wei Sun、Hao Fang、Wenfang Xu

  DOI：10.1016/j.bmcl.2012.09.031

  日期：2012.11

  A series of novel sorafenib derivatives, 9a-w, was designed and synthesized in high yields using various substituted anilines, and their antiproliferative activities against HCT116, PC-3 and MDA-MB-231 cell lines were also evaluated and described. All compounds exhibited potent antiproliferative activity against HCT116 and PC-3 cells with IC50 = 2.8-52.0 and 2.2-45.6 mu M; compounds 9p and 9q demonstrated competitive antiproliferative activities to sorafenib against all three cancer cell lines, the cytotoxicity of compound 9r is more potent than that of sorafenib. Compounds (9g, 9p, 9q and 9r) were chosen for further evaluation of the anti-angiogenesis activity, and showed the inhibition of sprout formation from aortic ring ex vivo. The structures of all the newly synthesized compounds were determined by H-1 NMR, C-13 NMR and HRMS. (C) 2012 Elsevier Ltd. All rights reserved.