(1-(3-methylphenyl)ethylidene)-thiosemicarbazide | 546112-25-8

• 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: (1-(3-methylphenyl)ethylidene)-thiosemicarbazide
• 英文别名: 1-(1-(3'-methylphenyl)ethylidene)thiosemicarbazide；3'-methylacetophenone thiosemicarbazone；[1-(3-Methylphenyl)ethylideneamino]thiourea
• CAS: 546112-25-8
• 化学式: C₁₀H₁₃N₃S
• 分子量: 207.299
• InChiKey: FJTIPXZSFGNVCS-UHFFFAOYSA-N

物化性质

• 沸点：
  346.2±35.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-(3-methylphenyl)ethylidene)-thiosemicarbazide 在 盐酸羟胺 、 sodium hydride 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 14.08h， 生成
  参考文献：
  名称：

  Discovery of thiosemicarbazone-containing compounds with potent anti-proliferation activity against drug-resistant K562/A02 cells

  摘要：

  P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a major obstacle to successful chemotherapy for leukemia. In this study, a series of thiosemicarbazone-containing compounds (4a-b, 7a-q) were synthesized. Biological evaluation showed that the most active compound 7e displayed potent anti-leukemia activity against P-gp overexpressing drug-resistant K562/A02 cells, with an IC₅₀ value of 0.44 μM. Notably, compound 7e exhibited a selective killing effect on K562/A02 cells by dose-dependently increasing the intracellular levels of reactive oxygen species (ROS), thus exerting a potential collateral sensitivity (CS)-promoting effect in vitro. Moreover, compound 7e could inhibit HDAC1 and HDAC6, and induce the apoptosis of K562/A02 cells by increasing the expression of Bax, decreasing Bcl-2 protein level, and promoting the cleavage of caspase-3 and PARP, respectively. Overall, 7e may be a potential anti-cancer agent against drug-resistant myelogenous leukemia.

  DOI：

  10.1016/j.bmcl.2020.127638
• 作为产物：
  描述：

  1-(3-甲基苯基)-2-苯乙酮 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以78%的产率得到(1-(3-methylphenyl)ethylidene)-thiosemicarbazide
  参考文献：
  名称：

  烷基取代苯甲醛或苯乙酮缩氨基硫脲衍生物 及其作为酪氨酸酶抑制剂的应用

  摘要：

  本发明公开了式I所示的烷基取代苯甲醛或苯乙酮缩氨基硫脲衍生物及其应用：其中，R1为氢或甲基；R2选自C2～C8的烷基、烯基、芳烃或取代的芳烃基团中的一种。本发明所涉及的化合物结构新颖、制备简单，对酪氨酸酶的抑制活性强，具有很明显的应用前景。

  公开号：

  CN105439926B

文献信息

• Spectroscopic characterization and quantum-chemical analysis of hydrazinyl thiazol-4(5H)-one functionalized materials to predict their key electronic and non-linear optical behavior
  作者：Hasnain Mehmood、Tashfeen Akhtar、Muhammad Haroon、Muhammad Khalid、Ataualpa A.C. Braga、Simon Woodward、Saad M. Alshehri、Muhammad Adnan Asghar

  DOI：10.1016/j.molstruc.2023.135798

  日期：2023.9

  Organic chromophores are desirable as efficient nonlinear optical (NLO) substances because of their structural tunability, easy synthesis and promising NLO response. Herein, we synthesized series of organic compounds (EHT1-EHT5) containing hydrazinylthiazol-4(5H)-one (HT) as a base and explored their nonlinear optical (NLO) properties through quantum chemical investigations. Novel hydrazinylthiazol-4(5H)-ones

  有机发色团因其结构可调性、易于合成和有前途的 NLO 响应而被视为高效的非线性光学 (NLO) 物质。在此，我们合成了一系列以 hydrazinylthiazol-4(5 H )-one ( HT ) 为基础的有机化合物 ( EHT1-EHT5 )，并通过量子化学研究探索了它们的非线性光学 (NLO) 特性。新型 hydrazinylthiazol-4(5 H )-ones 的合成是通过两步合成法。合成结构最初是通过不同的光谱技术解决的。通过高分辨率质谱 (HRMS) 实现了所制备结构的验证。密度泛函理论 (DFT) 研究在 M06/6–311 G (d,p) 泛函上进行。优化的结构用于执行进一步分析，包括前沿分子轨道 (FMO)、紫外-可见光 (UV-Vis)、自然键轨道 (NBO)、态密度 (DOS)、跃迁密度矩阵 (TDM) 以及非线性光学（非线性光学）特性。量子化学见解导致EHT3的最小E间隙(4
• Discovery of thiosemicarbazone-containing compounds with potent anti-proliferation activity against drug-resistant K562/A02 cells
  作者：Xiaoke Gu、Xin Li、Mingyu Guan、Chunyu Jiang、Qinghua Song、Nan Sun、Yueting Zou、Qingqing Zhou、Jing Chen、Jingying Qiu

  DOI：10.1016/j.bmcl.2020.127638

  日期：2020.12

  P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a major obstacle to successful chemotherapy for leukemia. In this study, a series of thiosemicarbazone-containing compounds (4a-b, 7a-q) were synthesized. Biological evaluation showed that the most active compound 7e displayed potent anti-leukemia activity against P-gp overexpressing drug-resistant K562/A02 cells, with an IC₅₀ value of 0.44 μM. Notably, compound 7e exhibited a selective killing effect on K562/A02 cells by dose-dependently increasing the intracellular levels of reactive oxygen species (ROS), thus exerting a potential collateral sensitivity (CS)-promoting effect in vitro. Moreover, compound 7e could inhibit HDAC1 and HDAC6, and induce the apoptosis of K562/A02 cells by increasing the expression of Bax, decreasing Bcl-2 protein level, and promoting the cleavage of caspase-3 and PARP, respectively. Overall, 7e may be a potential anti-cancer agent against drug-resistant myelogenous leukemia.
• 烷基取代苯甲醛或苯乙酮缩氨基硫脲衍生物 及其作为酪氨酸酶抑制剂的应用
  申请人：中国广州分析测试中心

  公开号：CN105439926B

  公开（公告）日：2017-12-01

  本发明公开了式I所示的烷基取代苯甲醛或苯乙酮缩氨基硫脲衍生物及其应用：其中，R1为氢或甲基；R2选自C2～C8的烷基、烯基、芳烃或取代的芳烃基团中的一种。本发明所涉及的化合物结构新颖、制备简单，对酪氨酸酶的抑制活性强，具有很明显的应用前景。