[3,4-dichlorophenyl]dithioic acid | 21878-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3,4-dichlorophenyl]dithioic acid
• 英文别名: (3,4-Dichlorophenyl)carbamodithioic acid
• CAS: 21878-59-1
• 化学式: C₇H₅Cl₂NS₂
• 分子量: 238.161
• InChiKey: LOKITQRXMMZMJV-UHFFFAOYSA-N

物化性质

• 沸点：
  310.2±52.0 °C(Predicted)
• 密度：
  1.568±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [3,4-dichlorophenyl]dithioic acid 在 三光气 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 N-[4-(3-amino-1H-indazol-4-yl)phenyl]-N'-(3,4-dichlorophenyl)thiourea
  参考文献：
  名称：

  Discovery of novel anti-angiogenesis agents. Part 8: Diaryl thiourea bearing 1 H -indazole-3-amine as multi-target RTKs inhibitors

  摘要：

  VEGFR-2, TIE-2, and EphB4 are essential for both angiogenesis and tumorigenesis. Herein, we designed and prepared three classes of multi-target inhibitors based on the extensive sequence homology along the kinase domain of angiogenic RTKs. Biological evaluation indicated that these multi-target inhibitors exhibited considerable potential as novel anti-angiogeneic and anticancer agents. Among them, a diaryl thiourea bearing 1H-indazole-3-amine (16a) displayed the most potent RTK inhibition and excellent selectivity. It also showed inhibition on viability of human umbilical vein endothelial cells and anti proliferation against a broad spectrum of cancer cells. Therefore, 1H-indazole-3-amine could serve as a promising hinge binding group for multi-target inhibitors of VEGFR-2, Tie-2, and EphB4. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.008
• 作为产物：
  描述：

  二硫化碳 、 3,4-二氯苯胺 在 三乙烯二胺 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以30%的产率得到[3,4-dichlorophenyl]dithioic acid
  参考文献：
  名称：

  一种具有抗肿瘤活性的二芳基硫脲化合物及其制备方法和应用

  摘要：

  本发明提供了一种具有抗肿瘤活性的二芳基硫脲化合物及其制备方法和应用，该化合物的结构式为其中R1、R2为卤素基团，或者R1、R2共同形成Ar为吡啶、吲唑或喹唑啉的含氮杂环。该化合物对VEGFR‑2激酶有很好的抑制活性，能够通过抑制VEGFR‑2激酶的活性，阻断其诱导的信号通路，抑制肿瘤细胞的增生和迁移，从而可应用于抗肿瘤药物的制备。且该化合物的制备方法具有原料易得，反应条件温和，反应过程操作简单，所用试剂便宜的优点。

  公开号：

  CN105924385A

文献信息

• 一种具有抗肿瘤活性的二芳基硫脲化合物及其制备方法和应用
  申请人：西安交通大学

  公开号：CN105924385A

  公开（公告）日：2016-09-07

  本发明提供了一种具有抗肿瘤活性的二芳基硫脲化合物及其制备方法和应用，该化合物的结构式为其中R1、R2为卤素基团，或者R1、R2共同形成Ar为吡啶、吲唑或喹唑啉的含氮杂环。该化合物对VEGFR‑2激酶有很好的抑制活性，能够通过抑制VEGFR‑2激酶的活性，阻断其诱导的信号通路，抑制肿瘤细胞的增生和迁移，从而可应用于抗肿瘤药物的制备。且该化合物的制备方法具有原料易得，反应条件温和，反应过程操作简单，所用试剂便宜的优点。
• COMPOUNDS WITH COPPER- OR ZINC-ACTIVATED TOXICITY AGAINST MICROBIAL INFECTION
  申请人：Kansas State University Research Foundation

  公开号：US20220024877A1

  公开（公告）日：2022-01-27

  Heterocyclic compounds with a novel pyrazole thioamide-based NNSN structural motif, having highly effective zinc- or copper-activated toxicity against microbial infections at micromolar or nanomolar minimum inhibitory concentrations (MIC), and methods of making and using same.

  具有新型吡唑硫酰胺基NNSN结构基元的杂环化合物，对微生物感染具有高效的锌或铜活化毒性，在微摩尔或纳摩尔最小抑制浓度（MIC）下，以及制备和使用这些化合物的方法。
• Discovery of novel anti-angiogenesis agents. Part 6: Multi-targeted RTK inhibitors
  作者：Lin Zhang、Yuanyuan Shan、Chuansheng Li、Ying Sun、Ping Su、Jinfeng Wang、Lisha Li、Xiaoyan Pan、Jie Zhang

  DOI：10.1016/j.ejmech.2016.12.059

  日期：2017.2

  Angiogenesis is modulated by a multitude of pro-angiogenic factors including VEGFR-2, Tie-2, and EphB4. Moreover, their crosstalk also had been well elaborated. We have identified several diarylureabased VEGFR-2 inhibitors as potential anti-angiogenesis agents. As a continuation to our previous research, two series of diaryl malonamide and diaryl thiourea derivatives have been developed as multiplex VEGFR-2/Tie-2/EphB4 inhibitors. Interestingly, the biological evaluation indicated that several compounds bearing trifluoromethyl or trifluoromethoxyl exhibited promising multiplex inhibition against angiogenesis-related VEGFR-2, Tie-2, and EphB4. The representative compound (18a) displayed both potent multi-targeted RTK inhibition and considerable antiproliferative activities against human umbilical vein endothelial cells (EA.hy926). These results will contribute to the discovery of novel mutitargeted anti-angiogenesis agents. (C) 2017 Elsevier Masson SAS. All rights reserved.
• [EN] COMPOUNDS WITH COPPER- OR ZINC-ACTIVATED TOXICITY AGAINST MICROBIAL INFECTION<br/>[FR] COMPOSÉS PRÉSENTANT UNE TOXICITÉ ACTIVÉE PAR DU CUIVRE OU DU ZINC CONTRE UNE INFECTION MICROBIENNE
  申请人：UNIV KANSAS STATE

  公开号：WO2020061412A1

  公开（公告）日：2020-03-26

  Heterocyclic compounds with a novel pyrazole thioamide-based NNSN structural motif, having highly effective zinc- or copper-activated toxicity against microbial infections at micromolar or nanomolar minimum inhibitory concentrations (MIC), and methods of making and using the same.
• Discovery of novel anti-angiogenesis agents. Part 8: Diaryl thiourea bearing 1 H -indazole-3-amine as multi-target RTKs inhibitors
  作者：Ying Sun、Yuanyuan Shan、Chuansheng Li、Ru Si、Xiaoyan Pan、Binghe Wang、Jie Zhang

  DOI：10.1016/j.ejmech.2017.10.008

  日期：2017.12

  VEGFR-2, TIE-2, and EphB4 are essential for both angiogenesis and tumorigenesis. Herein, we designed and prepared three classes of multi-target inhibitors based on the extensive sequence homology along the kinase domain of angiogenic RTKs. Biological evaluation indicated that these multi-target inhibitors exhibited considerable potential as novel anti-angiogeneic and anticancer agents. Among them, a diaryl thiourea bearing 1H-indazole-3-amine (16a) displayed the most potent RTK inhibition and excellent selectivity. It also showed inhibition on viability of human umbilical vein endothelial cells and anti proliferation against a broad spectrum of cancer cells. Therefore, 1H-indazole-3-amine could serve as a promising hinge binding group for multi-target inhibitors of VEGFR-2, Tie-2, and EphB4. (C) 2017 Elsevier Masson SAS. All rights reserved.