4-[1-(2-carbamothioylhydrazinylidene)ethyl]phenyl acetate | 18099-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-[1-(2-carbamothioylhydrazinylidene)ethyl]phenyl acetate
• CAS: 18099-74-6
• 化学式: C₁₁H₁₃N₃O₂S
• 分子量: 251.309
• InChiKey: VQTQQQITGUWKNC-UHFFFAOYSA-N

物化性质

• 沸点：
  390.5±44.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  76.71
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[1-(2-carbamothioylhydrazinylidene)ethyl]phenyl acetate 、 乙酸酐 反应 72.0h， 以46%的产率得到4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl acetate
  参考文献：
  名称：

  Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma

  摘要：

  Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.023
• 作为产物：
  描述：

  4-乙酰氧基苯并酮 、 氨基硫脲 以 乙醇 为溶剂， 反应 0.33h， 生成 4-[1-(2-carbamothioylhydrazinylidene)ethyl]phenyl acetate
  参考文献：
  名称：

  Synthesis, Cytotoxicity and Antitumor Activity of 4-[(1-(2-carbamothioylhydrazinylidene)ethyl]phenyl acetate (acesemi) Conjugated Chitosan Functionalized LaF₃:Ce³⁺, Tb³⁺ Nanoparticles

  摘要：

  采用简单的共沉淀法设计了壳聚糖功能化发光稀土掺杂铈、铽纳米粒子（LaF3:Ce3+, Tb3+/chi NPs），作为 4-[(1-(2-carbamothioylhydrazinylidene)乙基]苯基乙酸酯（acesemi）的药物载体。合成的壳聚糖功能化纳米粒子呈球形，平均直径为 10-12 纳米。它们具有水溶性和生物相容性，其表面的羟基和氨基官能团可用于合成抗癌药物 ace semi 的生物共轭。利用 X 射线衍射和透射电子显微镜研究了 ace semi 与 LaF3:Ce3+、Tb3+/chi NPs 结合的性质。紫外-可见光光谱、稳态和激发态荧光光谱分析了 ace semi 与 LaF3:Ce3+、Tb3+/chi NPs 之间因形成复合物而产生的交替相互作用。光物理表征得出的结论是，LaF3:Ce3+, Tb3+/chi NPs 对 ace semi 的吸附和释放速度较快，同时也证实这可能是由于药物的氮和氨基与纳米颗粒之间的氢键作用。当半王牌纳米粒子和 LaF3:Ce3+, Tb3+/chi 纳米粒子的化学计量比为 1:4 时，产量百分比和夹带效率最高，分别为 87.01 ± 0.91 和 84.34 ± 0.26。此外，抗肿瘤活性研究表明，与游离的 ace semi 相比，ace semi 共轭 LaF3:Ce3+、Tb3+/chi NPs 对 A549 肺癌细胞株的细胞毒性作用更强。

  DOI：

  10.1166/jnn.2017.13808