5-(3-chlorophenyl)-4-(4-methoxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione | 714214-94-5

• 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-(4-methoxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 3-(3-chlorophenyl)-4-(4-methoxyphenyl)-1H-1,2,4-triazole-5-thione
• CAS: 714214-94-5
• 化学式: C₁₅H₁₂ClN₃OS
• 分子量: 317.799
• InChiKey: UEOMQOQLZYAYOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 5-(3-chlorophenyl)-4-(4-methoxyphenyl)-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72%的产率得到7-[4-[[3-(3-Chlorophenyl)-4-(4-methoxyphenyl)-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：

  4-甲氧基苯基 异硫氰酸酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 5-(3-chlorophenyl)-4-(4-methoxyphenyl)-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 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。