(4-氯-3-(三氟甲基)苯基)氨基二硫代甲酸 | 56356-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-氯-3-(三氟甲基)苯基)氨基二硫代甲酸
• 英文名称: 3-trifluoromethyl-4-chlorophenyldithiocarbamic acid
• 英文别名: [4-Chloro-3-(trifluoromethyl)phenyl]carbamodithioic acid；[4-chloro-3-(trifluoromethyl)phenyl]carbamodithioic acid
• CAS: 56356-99-1
• 化学式: C₈H₅ClF₃NS₂
• 分子量: 271.715
• InChiKey: ZKEMZNUTVOKORN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-氯-3-(三氟甲基)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 4-(3-(3-(4-chloro-3-(trifluoromethyl)phenyl)thioureido)phenoxy)-N-cyclopropylpicolinamide
  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：

  2-氯-5-氨基三氟甲苯 在 三乙烯二胺 、 二硫化碳 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (4-氯-3-(三氟甲基)苯基)氨基二硫代甲酸
  参考文献：
  名称：

  一类含尼克酰胺砌块的二苯基硫脲化合物及 其盐的制备方法和用途

  摘要：

  本发明涉及一类含尼克酰胺砌块的二苯基硫脲化合物及其盐，该类化合物具有如通式（Ⅰ）的化学结构；该类化合物或其药学上可以接受的盐具有对多种肿瘤细胞株的抑制作用，可作为有效成分用于制备肿瘤方面的治疗药物。

  公开号：

  CN104710355B

文献信息

• 一种含芳胺结构的硫脲类化合物及其制备方 法和应用
  申请人：烟台大学

  公开号：CN104045598B

  公开（公告）日：2017-02-15

  本发明公开了一种含芳胺结构的硫脲类化合物，包括具有通式Ⅰ化合物或其药学上可接受的盐，R1选自H,C1‑C8的烷基，卤素，‑CF3,‑OCF3，‑NO2,‑CN,R2O‑,‑SO2NH2,‑NHSO2R3，‑NR4R5，‑CONR6R7，‑COOR8，R9CO‑以及它们的二取代或三取代的组合，其中R2,R3,R4,R5,R6,R7,R8,R9分别为H或C1‑C8的烃基；L选自‑NHR10、‑NHOR11、‑NR12R13、其中R10,R11,R12,R13分别为H或C1‑C8的烷基、环烷基或芳基。本发明所述化合物具有对多种肿瘤细胞株的抑制作用。
• 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 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.
• Thiazolidinone CFTR inhibitors with improved water solubility identified by structure–activity analysis
  作者：N.D. Sonawane、A.S. Verkman

  DOI：10.1016/j.bmc.2008.07.044

  日期：2008.9

  The thiazolidinone 3-[(3-trifluoromethyl)phenyl]-5-[(4-carboxyphenyl)methylene]-2-thioxo-4-thiazolidinone (CFTRinh-172) inhibits cystic fibrosis transmembrane conductance regulator ( CFTR) chloride channel conductance with submicromolar affinity and blocks cholera toxin-induced intestinal fluid secretion. Fifty-eight CFTRinh-172 analogs were synthesized to identify CFTR inhibitors with improved water solubility, exploring modi. cations in its two phenyl rings, thiazolidinone core, and core-phenyl connectors. Greatest CFTR inhibition potency was found for 3-CF3 and polar group-substituted-phenyl rings, and a thiazolidinone core. Two compounds with similar to 1 mu M CFTR inhibition potency and solubility >180 mu M(>10-fold more than CFTRinh-172) were identified: Tetrazolo-172, containing 4-tetrazolophenyl in place of 4-carboxyphenyl, and Oxo-172, containing thiazolidinedione in place of the thiazolidinone core. These water soluble thiazolidinone analogs had low cellular toxicity. The improved water solubility of Tetrazolo- and Oxo-172 make them potential lead candidates for therapy of secretory diarrheas and polycystic kidney disease. (C) 2008 Elsevier Ltd. All rights reserved.