3,4-dichloroacetophenone thiosemicarbazone

• 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-dichloroacetophenone thiosemicarbazone
• 英文别名: 3',4'-dichloroacetophenone thio semicarbazone；3',4'-Dichloroacetophenonethiosemicarbazone；[(E)-1-(3,4-dichlorophenyl)ethylideneamino]thiourea
• 化学式: C₉H₉Cl₂N₃S
• 分子量: 262.163
• InChiKey: WLYQLQVFJXFMJD-WLRTZDKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  3,4-dichloroacetophenone thiosemicarbazone 以 乙醇 、 水 、 丙酮 为溶剂， 生成 [Pd2(3,4-dichloroacetophenone thiosemicarbazone)2(trans-bis(diphenylphosphino)ethylene)]
  参考文献：
  名称：

  Cyclopalladated complexes containing tridentate thiosemicarbazone ligands of biological significance: Synthesis, structure and antimalarial activity

  摘要：

  The C-H activation reaction of two aryl-derived thiosemicarbazones with K-2[PdCl4] affords tetranuclear cyclopalladated complexes (3 and 4) where the thiosemicarbazone ligand acts as a tridentate donor [C,N,S] coordinated to palladium via the ortho-carbon of the aryl ring, imine nitrogen and thiolato sulfur. The palladiumesulfur bridging coordination bonds give rise to a Pd4S4 core. These Pd-S-bridging bonds were cleaved with a variety of mono-and bis-phosphines to give a series of mono, di and tetranuclear organopalladium complexes (5-12) where the phosphorus atom coordinates to palladium trans to the imine nitrogen. All of the complexes were fully characterized using various analytical and spectroscopic techniques. These palladium complexes along with their free ligands were evaluated as bioorganometallic antimalarial agents against two Plasmodium falciparum strains, 3D7 (chloroquine sensitive) and K1 (chloroquine and pyrimethamine resistant). Some of the complexes were found to be moderate inhibitors of parasite growth and were more active than the corresponding free ligand. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.06.010
• 作为产物：
  描述：

  氨基硫脲 、 3,4-二氯苯乙酮 在 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 生成 3,4-dichloroacetophenone thiosemicarbazone
  参考文献：
  名称：

  新的噻唑基hydr衍生物的合成及其抗结核活性。

  摘要：

  耐药性分枝杆菌病原体的临床重要性日益提高，这为微生物学研究和新的抗分枝杆菌化合物的开发提供了额外的紧迫性。为此目的，合成了新的噻唑基hydr衍生物，并评估了其抗结核活性。硫代氨基脲与苯乙酮衍生物反应，得到1-（1-芳基亚乙基）硫代氨基脲（1）。通过使1-（1-芳基亚乙基）硫代氨基脲与1-（5）反应合成N-（1-芳基亚乙基）-N'-[4-（茚满-5-基）噻唑-2-基] hydr（3）衍生物。 -茚满基）-2-溴乙酮（2）。通过元素分析，IR，（1）1 H NMR，MS-FAB（+）光谱数据阐明了化合物的化学结构。合成的化合物的抗结核活性通过肉汤微量稀释测定法，Microplate Alamar蓝测定法，使用BACTEC 460辐射系统对结核分枝杆菌H（37）Rv（ATCC 27294）的浓度为6.25微克/毫升，在BACTEC12B培养基中进行体外筛选，某些受试化合物显示出重要的抑制作用，范

  DOI：

  10.1016/j.ejmech.2007.07.001

文献信息

• Thiosemicarbazone derivatives: Evaluation as cruzipain inhibitors and molecular modeling study of complexes with cruzain
  作者：Gabriel Jasinski、Emir Salas-Sarduy、Daniel Vega、Lucas Fabian、María Florencia Martini、Albertina G. Moglioni

  DOI：10.1016/j.bmc.2022.116708

  日期：2022.5

  site of cruzain and the contribution of geometric parameters to the possible mechanism of action involved in the observed inhibition. Finally, from some geometric parameters analyzed on modeled TSC-cruzain complexes, a semi-quantitative relationship was established that could explain the inhibitory activity of thiosemicarbazones on cruzipain, the enzyme actually present in the parasite.

  cruzipain 抑制剂的开发是寻找治疗南美锥虫病药物的最具吸引力的挑战之一。这种酶的重组形式 cruzain 已经与许多抑制剂一起结晶，不包括氨基硫脲。这些化合物已被确定为 cruzain 的有效抑制剂，尽管文献中很少有关于在 cruzipain 上测试的氨基硫脲的数据。在这项工作中，我们展示了从T. cruzi中分离出来的 11 种氨基硫脲对 cruzipain 的评估结果epimastigotes，其中六个以前在 cruzain 上进行过评估。对于后者，我们通过计算方法研究了与 cruzain 活性位点的相互作用模式以及几何参数对观察到的抑制所涉及的可能作用机制的贡献。最后，从对建模的 TSC-cruzain 复合物分析的一些几何参数中，建立了一种半定量关系，可以解释氨基硫脲对 cruzipain 的抑制活性，cruzipain 是寄生虫中实际存在的酶。
• Gold(i) derived thiosemicarbazone complexes with rare halogen–halogen interaction–reduction of [Au(damp-C1,N)Cl2]
  作者：Setshaba D. Khanye、Nikoletta B. Báthori、Gregory S. Smith、Kelly Chibale

  DOI：10.1039/b925037a

  日期：——

  An attempt to prepare gold(III) complexes of thiosemicarbazones with the starting material gold(III) [Au(damp-C1,N)Cl2] led instead to gold(I) complexes with a rare Cl⋯Cl interaction.

  尝试做准备 金（III） 硫半脲与起始原料的配合物 金（III）[Au（damp-C 1，N）Cl 2 ]改为导致金（I） 罕见的配合物 氯⋯ 相互作用。
• Synthesis and Structure−Activity Relationship Study of Potent Trypanocidal Thio Semicarbazone Inhibitors of the Trypanosomal Cysteine Protease Cruzain
  作者：Xiaohui Du、Chun Guo、Elizabeth Hansell、Patricia S. Doyle、Conor R. Caffrey、Tod P. Holler、James H. McKerrow、Fred E. Cohen

  DOI：10.1021/jm010459j

  日期：2002.6.1

  American trypanosomiasis, or Chagas' disease, is the leading cause of heart disease in Latin America. Currently there is an urgent need to develop antitrypanosomal therapy due to the toxicity of existing agents and emerging drug resistance. A novel series of potent thio semicarbazone small-molecule inhibitors of the Trypanosoma cruzi cysteine protease cruzain have been identified. Some of these inhibitors have been shown to be trypanocidal. We initially discovered that X-bromopropiophenone thio semicarbazone (1i) inhibited cruzain and could cure mammalian cell cultures infected with T cruzi. 3'-Bromopropiophenone thio semicarbazone showed no toxicity for mammalian cells at concentrations that were trypanocidal. Following this lead, more than 100 compounds were designed and synthesized. A specific structure-activity relationship (SAR) was established, and many potent analogues with IC50 values in the low nanomolar range were identified. Eight additional analogues were trypanocidal in a cell culture assay, and this indicates that aryl thio semicarbazone is a productive scaffold for killing the parasites. Kinetic studies show that these are time-dependent inhibitors. Molecular modeling studies of the enzyme-inhibitor complex have led to a proposed mechanism of interaction as well as insight into the SAR of the thio semicarbazone series. The nonpeptide nature of this series, small size, and extremely low cost of production suggest this is a promising direction for the development of new antitrypanosome chemotherapy.
• Khanye, Setshaba D.; Wan, Baojie; Franzblau, Scott G., Journal of Organometallic Chemistry, 2011, vol. 696, p. 3392 - 3396
  作者：Khanye, Setshaba D.、Wan, Baojie、Franzblau, Scott G.、Gut, Jiri、Rosenthal, Philip J.、et al.

  DOI：——

  日期：——