1-(3-chlorobenzoyl)-4-(4-fluorophenyl)thiosemicarbazide | 316151-86-7

• 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-chlorobenzoyl)-4-(4-fluorophenyl)thiosemicarbazide
• 英文别名: 1-[(3-chlorophenyl)carbonyl]-4-(4-fluorophenyl)thiosemicarbazide；1-[(3-Chlorobenzoyl)amino]-3-(4-fluorophenyl)thiourea
• CAS: 316151-86-7
• 化学式: C₁₄H₁₁ClFN₃OS
• 分子量: 323.778
• InChiKey: CHHJVOVEOQPRTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-chlorobenzoyl)-4-(4-fluorophenyl)thiosemicarbazide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 5-(3-chlorophenyl)-4-(4-fluorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Halogen Substituents as an Effective Modulators of Antibacterial Activity of Substituted 1,2,4-triazole-3-thiones

  摘要：

  Fourteen novel compounds were obtained and their chemical structures were established by H-1-NMR and IR spectra as well as elemental analyses. As one of the most important factors determining the changes of activity of respective fluorophenyl and iodophenyl derivatives, one should consider the volume of halogen substituent and its influence on the lipophilicity of the entire molecule.

  DOI：

  10.2174/157018012804586987
• 作为产物：
  描述：

  4-氟苯基异硫氰酸酯 、 3-氯苯甲酰肼 以 乙醇 为溶剂， 反应 0.08h， 以85%的产率得到1-(3-chlorobenzoyl)-4-(4-fluorophenyl)thiosemicarbazide
  参考文献：
  名称：

  Studies on the Anticonvulsant Activity and Influence on GABA-ergic Neurotransmission of 1,2,4-Triazole-3-thione- Based Compounds

  摘要：

  本研究测试了几种 1,2,4-三唑-3-硫酮衍生物对小鼠最大电休克诱发癫痫发作的抗惊厥活性。所有活性化合物的特点都是起效迅速、作用持久。结构-活性观察结果表明，当 1,2,4-三唑核上连接的苯基环中至少有一个在对位上具有取代基时，化合物具有抗惊厥活性的几率要高得多。此外，研究结果还让我们得出结论：尽管洛雷克唑（第二代抗惊厥药物）和标题化合物的结构相似，但它们的抗惊厥活性是通过完全不同的分子机制实现的。

  DOI：

  10.3390/molecules190811279

文献信息

• Synthesis and antimicrobial activity of thiosemicarbazides, s-triazoles and their Mannich bases bearing 3-chlorophenyl moiety
  作者：Tomasz Plech、Monika Wujec、Agata Siwek、Urszula Kosikowska、Anna Malm

  DOI：10.1016/j.ejmech.2010.11.010

  日期：2011.1

  efficient synthesis of some 1,4-disubstituted thiosemicarbazide derivatives is described. The reaction of 3-chlorobenzoic acid hydrazide with various aryl isothiocyanates gave thiosemicarbazide derivatives (1–11) in good yield. The cyclization of compounds (1–11) in the presence of 2% NaOH resulted in the formation of compounds (12–22) containing the 1,2,4-triazole ring. A series of new Mannich bases (23–33)

  描述了一些1，4-二取代的硫代氨基脲衍生物的快速有效的合成。的3-氯苯甲酸酰肼与各种芳基异硫氰酸酯反应，得到氨基硫脲衍生物（1 - 11以良好的收率）。化合物（的环化1 - 11）在2％的NaOH的存在导致在化合物（形成12 - 22），其含有1,2,4-三唑环。还合成了与1,2,4-三唑结构有关的一系列新的曼尼希碱（23 – 33）。所有这些化合物均经过体外测试对有氧细菌参考菌株的抗菌活性-6革兰氏阳性和3革兰氏阴性; 还检查了12株金黄色葡萄球菌临床分离株。试图阐明取代基的性质/位置对所述化合物的抗菌活性的影响。
• Halogen Substituents as an Effective Modulators of Antibacterial Activity of Substituted 1,2,4-triazole-3-thiones
  作者：Tomasz Plech、Monika Wujec、Urszula Kosikowska、Anna Malm

  DOI：10.2174/157018012804586987

  日期：2012.12.1

  Fourteen novel compounds were obtained and their chemical structures were established by H-1-NMR and IR spectra as well as elemental analyses. As one of the most important factors determining the changes of activity of respective fluorophenyl and iodophenyl derivatives, one should consider the volume of halogen substituent and its influence on the lipophilicity of the entire molecule.
• Studies on the Anticonvulsant Activity and Influence on GABA-ergic Neurotransmission of 1,2,4-Triazole-3-thione- Based Compounds
  作者：Tomasz Plech、Barbara Kaproń、Jarogniew Łuszczki、Monika Wujec、Agata Paneth、Agata Siwek、Marcin Kołaczkowski、Maria Żołnierek、Gabriel Nowak

  DOI：10.3390/molecules190811279

  日期：——

  The anticonvulsant activity of several 1,2,4-triazole-3-thione derivatives on mouse maximal electroshock-induced seizures was tested in this study. Characteristic features of all active compounds were rapid onset of action and long lasting effect. Structure-activity observations showed that the probability of obtaining compounds exerting anticonvulsant activity was much higher when at least one of the phenyl rings attached to 1,2,4-triazole nucleus had a substituent at the para position. The obtained results, moreover, permit us to conclude that despite the structural similarity of loreclezole (second-generation anticonvulsant drug) and the titled compounds, their anticonvulsant activity is achieved via completely different molecular mechanisms.

  本研究测试了几种 1,2,4-三唑-3-硫酮衍生物对小鼠最大电休克诱发癫痫发作的抗惊厥活性。所有活性化合物的特点都是起效迅速、作用持久。结构-活性观察结果表明，当 1,2,4-三唑核上连接的苯基环中至少有一个在对位上具有取代基时，化合物具有抗惊厥活性的几率要高得多。此外，研究结果还让我们得出结论：尽管洛雷克唑（第二代抗惊厥药物）和标题化合物的结构相似，但它们的抗惊厥活性是通过完全不同的分子机制实现的。