4-(4-bromophenyl)-5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione | 1403137-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-bromophenyl)-5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 4-(4-Bromophenyl)-5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-1,2,4-triazole-3-thione；4-(4-bromophenyl)-5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-1,2,4-triazole-3-thione
• CAS: 1403137-49-4
• 化学式: C₁₉H₁₈BrClN₄OS
• 分子量: 465.801
• InChiKey: SFRLUTAJBILIRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(4-bromophenyl)-1-(4-chlorobenzoyl)thiosemicarbazide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-(4-bromophenyl)-5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  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

• Microbiologically active Mannich bases derived from 1,2,4-triazoles. The effect of C-5 substituent on antibacterial activity
  作者：Tomasz Plech、Monika Wujec、Magdalena Majewska、Urszula Kosikowska、Anna Malm

  DOI：10.1007/s00044-012-0248-y

  日期：2013.5

  the antibacterial activity of the Mannich bases derived from 4,5-disubstituted 1,2,4-triazole-3-thiones. This activity was considerably increased by an introduction of a chlorine atom to the phenyl ring. The obtained compounds were particularly active against opportunistic bacteria (Bacillus subtilis and Bacillus cereus). The antibacterial activity of some Mannich bases was similar or higher than the

  我们的研究证明，C-5 取代基的化学性质显着决定了衍生自 4,5-二取代 1,2,4-三唑-3-硫酮的曼尼希碱的抗菌活性。通过在苯环中引入氯原子，该活性显着​​增加。获得的化合物对机会性细菌（枯草芽孢杆菌和蜡状芽孢 杆菌）特别有效。某些曼尼希碱的抗菌活性与氨苄西林、头孢呋辛等常用抗生素的抗菌活性相似或更高。
• 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。
• The antinociceptive effect of 4-substituted derivatives of 5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione in mice
  作者：Listos Joanna、Sylwia Talarek、Jolanta Orzelska、Sylwia Fidecka、Monika Wujec、Tomasz Plech

  DOI：10.1007/s00210-013-0938-0

  日期：2014.4

  The aim of the present experiments was to examine the antinociceptive activity of 4-substituted derivatives of 5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione in mice. The compounds were synthesized using the so-called Mannich reaction and their structures were confirmed using IR and 1H-NMR spectra. The antinociceptive activity was investigated in two behavioral tests: the hot plate test and the writhing test. For preliminary estimation of other behavioral effects, the locomotor activity of mice, the motor coordination in the rota-rod test, and the myorelaxation in the chimney test were also studied. The changes in body temperature of animals were also recorded. We demonstrated that all examined compounds produced antinociceptive effect, both in the hot plate test and in the writhing test, without impact on the motor coordination and myorelaxation of animals. The pharmacological effect of all drugs has been developed within 60 min after administration of drugs; and in two cases (T-103 and T-104), it has been a short-lasting effect (up to 90 min). Two compounds (T-100 and T-102) also inhibited the locomotor activity of animals. T-104 induced the changes in body temperature of mice. Generally, we demonstrated that combination of two different heterocyclic systems (morpholine and 1,2,4-triazole) might be beneficial for reduction of nociception.