5-(3-chlorophenyl)-4-(2,4-difluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione | 1426945-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-chlorophenyl)-4-(2,4-difluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• CAS: 1426945-59-6
• 化学式: C₁₄H₈ClF₂N₃S
• 分子量: 323.753
• InChiKey: BTDHELKAUIUSFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.61
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 5-(3-chlorophenyl)-4-(2,4-difluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 、 环丙沙星 以 乙醇 为溶剂， 反应 12.0h， 以66%的产率得到7-[4-[[3-(3-Chlorophenyl)-4-(2,4-difluorophenyl)-5-sulfanylidene-1,2,4-triazol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vitro activity of 1,2,4-triazole-ciprofloxacin hybrids against drug-susceptible and drug-resistant bacteria

  摘要：

  A series of novel 1,2,4-triazole-ciprofloxacin hybrids was designed, synthesised and evaluated in vitro against drug-susceptible and drug-resistant bacteria. A significant part of the compounds obtained showed antibacterial activity higher than the activity of ciprofloxacin, both towards Gram-positive and Gram-negative species. Despite relatively small number of synthesised derivatives, it was possible to observe important dependences between their structure and activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.040
• 作为产物：
  描述：

  3-氯苯甲酰肼 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 5-(3-chlorophenyl)-4-(2,4-difluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis and in vitro activity of 1,2,4-triazole-ciprofloxacin hybrids against drug-susceptible and drug-resistant bacteria

  摘要：

  A series of novel 1,2,4-triazole-ciprofloxacin hybrids was designed, synthesised and evaluated in vitro against drug-susceptible and drug-resistant bacteria. A significant part of the compounds obtained showed antibacterial activity higher than the activity of ciprofloxacin, both towards Gram-positive and Gram-negative species. Despite relatively small number of synthesised derivatives, it was possible to observe important dependences between their structure and activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.040

文献信息

• Synthesis and Antibacterial Activity of 4,5-disubstituted-1,2,4-triazole-3- thiones
  作者：Tomasz Plech、Monika Wujec、Urszula Kosikowska、Anna Malm

  DOI：10.2174/15701808113109990082

  日期：2013.10.1

  Sixteen derivatives of 1,2,4-triazole-3-thione were obtained starting from 3-chlorobenzoic acid hydrazide. Structures of the investigated compounds were confirmed by 1H NMR, IR and elemental analyses. 4-(2,4- Dichlorophenyl)-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione exhibited the highest antibacterial activity, which exceeded the activity of commonly used antibiotics (ampicillin, cefuroxime) against Bacillus cereus ATCC10876. The obtained results allowed verification of the previously formulated hypothesis of a correlation between the molecules’ dipole moment values and their antibacterial activity.

  以3-氯苯甲酰肼为原料，得到16种1,2,4-三唑-3-硫酮衍生物。 所研究化合物的结构通过 1H NMR、IR 和元素分析得到证实。 4-(2,4- 二氯苯基)-5-(3-氯苯基)-2,4-二氢-3H-1,2,4-三唑-3-硫酮表现出最高的抗菌活性， 超过了常用抗生素（氨苄西林、头孢呋辛）对蜡样芽孢杆菌 ATCC10876 的活性。 获得的结果验证了先前提出的分子之间相关性的假设 偶极矩值及其抗菌活性。