1-(phenyl(p-tolyl)methylene)thiosemicarbazide | 137482-73-6

• 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-(phenyl(p-tolyl)methylene)thiosemicarbazide
• 英文别名: [[(4-Methylphenyl)-phenylmethylidene]amino]thiourea；[[(4-methylphenyl)-phenylmethylidene]amino]thiourea
• CAS: 137482-73-6
• 化学式: C₁₅H₁₅N₃S
• 分子量: 269.37
• InChiKey: DZOZYORQEZEOCT-UHFFFAOYSA-N

物化性质

• 沸点：
  424.1±38.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.41
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(phenyl(p-tolyl)methylene)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：

  4-甲基二苯甲酮 、 氨基硫脲 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 以63%的产率得到1-(phenyl(p-tolyl)methylene)thiosemicarbazide
  参考文献：
  名称：

  通过双重抑制水肿和中性粒细胞募集，设计和合成具有体内抗炎活性的新型二苯甲酮衍生物

  摘要：

  通过分子杂交设计了一系列含有噻唑杂环核的新型二苯甲酮衍生物。分子对接研究证明了设计的化合物对环氧合酶 (COX) 同工酶的抑制潜力。通过巴豆油诱导的耳水肿试验合成、表征并评估这些化合物的抗炎特性，以检查它们对前列腺素 (PG) 产生和中性粒细胞募集的影响。噻唑衍生物在减轻耳部水肿方面显示出有效的作用。分析表明，二苯甲酮衍生物结构上4-苯基-2-肼基噻唑的存在和C4'-OCH3的不存在与PG产生的抑制密切相关。此外，导数 2e，3a 和 3c 同时抑制 PG 产生和中性粒细胞募集，这可能是一种比普通 NSAID 更好的作用机制，因为它们无法抑制中性粒细胞募集。因此，这些化合物可以被认为是开发具有创新作用机制的新型抗炎药的潜在先导化合物。

  DOI：

  10.3390/molecules23081859

文献信息

• Mercury(II) acetate-assisted oxidative hydrolysis of thiosemicarbazones of benzaldehyde, acetophenone and benzophenone by potassium bromate
  作者：Kalyani Ramakrishnan、Vangalur S. Srinivasan

  DOI：10.1039/p29910001523

  日期：——

  Thiosemicarbazones of benzaldehydes, acetophenones and benzophenones are oxidatively hydrolysed by potassium bromate, Br(v)}, in the presence of mercury(II) acetate, as Hg(II) forms a complex with sulphur atoms, increasing the lability of the N-H bond. The rates of these reactions are less susceptible to the electronic influence of the substituents at the phenyl ring compared with other oxidants, showing that N-bromate ester formation is the rate-determining step of this reaction. Such N-bromate ester formation seems to occur more readily with Hg(II)-sulphur complexes.
• 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.
• Design and Synthesis of New Benzophenone Derivatives with In Vivo Anti-Inflammatory Activity through Dual Inhibition of Edema and Neutrophil Recruitment
  作者：Jaqueline Januario、Thiago de Souza、Stefânia Lavorato、Tatiane Maiolini、Olívia Domingos、João Baldim、Laís Folquitto、Marisi Soares、Daniela Chagas-Paula、Danielle Dias、Marcelo dos Santos

  DOI：10.3390/molecules23081859

  日期：——

  examine their effect on both prostaglandin (PG) production and neutrophils recruitment. The thiazole derivatives displayed a potent effect in terms of reducing ear edema. The analysis suggested that the presence of 4-phenyl-2-hydrazinothiazole and the absence of C4′-OCH3 on the benzophenone derivative structure are strongly related to the inhibition of PG production. In addition, the derivatives 2e, 3a and

  通过分子杂交设计了一系列含有噻唑杂环核的新型二苯甲酮衍生物。分子对接研究证明了设计的化合物对环氧合酶 (COX) 同工酶的抑制潜力。通过巴豆油诱导的耳水肿试验合成、表征并评估这些化合物的抗炎特性，以检查它们对前列腺素 (PG) 产生和中性粒细胞募集的影响。噻唑衍生物在减轻耳部水肿方面显示出有效的作用。分析表明，二苯甲酮衍生物结构上4-苯基-2-肼基噻唑的存在和C4'-OCH3的不存在与PG产生的抑制密切相关。此外，导数 2e，3a 和 3c 同时抑制 PG 产生和中性粒细胞募集，这可能是一种比普通 NSAID 更好的作用机制，因为它们无法抑制中性粒细胞募集。因此，这些化合物可以被认为是开发具有创新作用机制的新型抗炎药的潜在先导化合物。