2-(4-phenoxyphenoxy)ethyl thiocyanate | 205381-53-9

• 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: 2-(4-phenoxyphenoxy)ethyl thiocyanate
• 英文别名: 4-phenoxyphenoxyethyl thiocyanate；WC-9
• CAS: 205381-53-9
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: YQZHGQYIMXWEHI-UHFFFAOYSA-N

物化性质

• 熔点：
  52 °C
• 沸点：
  435.4±30.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  67.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-phenoxyphenoxy)ethyl thiocyanate 在 吡啶 、 sodium methylate 、 溶剂黄146 、 锌 作用下， 反应 19.0h， 生成 Ethylsulfanyl-[2-(4-phenoxyphenoxy)ethylsulfanyl]methanone
  参考文献：
  名称：

  Structure−Activity Relationship of New Growth Inhibitors of Trypanosoma cruzi

  摘要：

  Several drugs bearing the 4-phenoxyphenoxy skeleton and other closely related structures were designed, synthesized, and evaluated as antiproliferative agents against Trypanosoma cruzi, the etiologic agent of Chagas' disease. The new class of drugs was envisioned by modifying the nonpolar 4-phenoxyphenoxy moiety replacing selected aromatic protons by different groups via electrophilic aromatic substitution reactions as well as introducing a sulfur atom at the polar extreme. Of the designed compounds, sulfur-containing derivatives were shown to be potent antireplicative agents against T. cruzi. Among these drugs, 4-phenoxyphenoxyethyl thiocyanate (compound 56) proved to be an extremely active growth inhibitor of the epimastigote forms of T. cruzi and displayed an IC50 of 2.2 mu M. Under the same assay conditions, this drug was much more active than Nifurtimox, one of the drugs currently in clinical use to control this disease. This thiocyanate derivative was also a very active inhibitor against the intracellular form of the parasite at the nanomolar level. Other sulfur derivatives prepared also exhibited very potent antiproliferative action against T. cruzi. The presence of a sulfur atom at the polar extreme for this family of compounds seems to be very important for biological action because this atom was always associated with high inhibition values. 4-Phenoxyphenoxyethyl thiocyanate presents very good prospective not only as a lead drug but also as a potential chemotherapeutic agent.

  DOI：

  10.1021/jm970860z
• 作为产物：
  描述：

  2-(4-苯氧基苯氧基)乙醇 在 吡啶 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(4-phenoxyphenoxy)ethyl thiocyanate
  参考文献：
  名称：

  Structure−Activity Relationship of New Growth Inhibitors of Trypanosoma cruzi

  摘要：

  Several drugs bearing the 4-phenoxyphenoxy skeleton and other closely related structures were designed, synthesized, and evaluated as antiproliferative agents against Trypanosoma cruzi, the etiologic agent of Chagas' disease. The new class of drugs was envisioned by modifying the nonpolar 4-phenoxyphenoxy moiety replacing selected aromatic protons by different groups via electrophilic aromatic substitution reactions as well as introducing a sulfur atom at the polar extreme. Of the designed compounds, sulfur-containing derivatives were shown to be potent antireplicative agents against T. cruzi. Among these drugs, 4-phenoxyphenoxyethyl thiocyanate (compound 56) proved to be an extremely active growth inhibitor of the epimastigote forms of T. cruzi and displayed an IC50 of 2.2 mu M. Under the same assay conditions, this drug was much more active than Nifurtimox, one of the drugs currently in clinical use to control this disease. This thiocyanate derivative was also a very active inhibitor against the intracellular form of the parasite at the nanomolar level. Other sulfur derivatives prepared also exhibited very potent antiproliferative action against T. cruzi. The presence of a sulfur atom at the polar extreme for this family of compounds seems to be very important for biological action because this atom was always associated with high inhibition values. 4-Phenoxyphenoxyethyl thiocyanate presents very good prospective not only as a lead drug but also as a potential chemotherapeutic agent.

  DOI：

  10.1021/jm970860z

文献信息

• Further insights of selenium-containing analogues of WC-9 against Trypanosoma cruzi
  作者：María N. Chao、María V. Lorenzo-Ocampo、Sergio H. Szajnman、Roberto Docampo、Juan B. Rodriguez

  DOI：10.1016/j.bmc.2019.02.039

  日期：2019.4

  searching for new chemotherapeutic agents against American trypanosomiasis (Chagas disease), new selenocyanate derivatives were designed, synthesized and biologically evaluated against the clinically more relevant dividing form of Trypanosoma cruzi, the etiologic agent of this illness. In addition, in order to establish the role of each part of the selenocyanate moiety, different derivatives, in which

  作为我们旨在寻找针对美国锥虫病（Chagas病）的新化学治疗剂的项目的延续，针对该疾病的病原体克氏锥虫的临床上更相关的划分形式，设计，合成了新的硒氰酸酯衍生物，并对其进行了生物学评估。另外，为了确立硒氰酸酯部分的每个部分的作用，构思，合成和生物学评估了其中不存在硒原子或氰基的不同衍生物。此外，为了研究末端苯氧基的最佳位置，合成了新的WC-9区域异构体，并针对克鲁氏梭菌进行了评估。最后，WC-9的强效构象刚性类似物的外消旋混合物的拆分已完成，并已进一步测试过，可作为克氏锥虫增殖的生长抑制剂。该结果提供了关于硒氰酸酯基团在其抗寄生虫活性中的作用的进一步见解。