7-[4-{[4-(3,5-dichlorophenyl)-3-(3-hydroxyphenyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1426945-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-[4-{[4-(3,5-dichlorophenyl)-3-(3-hydroxyphenyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-cyclopropyl-6-fluoro-7-[4-{[4-(3,5-dichlorophenyl)-3-(3-hydroxyphenyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid；1-Cyclopropyl-7-[4-[[4-(3,5-dichlorophenyl)-3-(3-hydroxyphenyl)-5-sulfanylidene-1,2,4-triazol-1-yl]methyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-7-[4-[[4-(3,5-dichlorophenyl)-3-(3-hydroxyphenyl)-5-sulfanylidene-1,2,4-triazol-1-yl]methyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 1426945-81-4
• 化学式: C₃₂H₂₇Cl₂FN₆O₄S
• 分子量: 681.575
• InChiKey: JJIORDDWVHOGHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-羟基苯酰肼 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.08h， 生成 7-[4-{[4-(3,5-dichlorophenyl)-3-(3-hydroxyphenyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-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

文献信息

• Determination of the Primary Molecular Target of 1,2,4-Triazole-Ciprofloxacin Hybrids
  作者：Tomasz Plech、Barbara Kaproń、Agata Paneth、Urszula Kosikowska、Anna Malm、Aleksandra Strzelczyk、Paweł Stączek、Łukasz Świątek、Barbara Rajtar、Małgorzata Polz-Dacewicz

  DOI：10.3390/molecules20046254

  日期：——

  We have synthesized and examined the antibacterial activity, toxicity and affinity towards bacterial type II topoisomerases of a series of 1,2,4-triazole-ciprofloxacin hybrids. A number of these compounds displayed enhanced activity against Gram-positive and Gram-negative bacteria when compared to ciprofloxacin. The toxic concentrations of the obtained derivatives, evaluated on HEK-293 cells using MTT assay, were much higher than concentrations required to produce antibacterial effect. Finally, the results of enzymatic studies showed that the analyzed compounds demonstrated other preferences as regards primary and secondary molecular targets than ciprofloxacin.

  我们合成并研究了一系列 1,2,4-噁唑-环丙沙星杂合物的抗菌活性、毒性和对细菌II型拓扑异构酶的亲和力。这些化合物中有不少在抗击革兰氏阳性和革兰氏阴性细菌方面表现出比环丙沙星更强的活性。通过 MTT 试验评估得到的衍生物的毒性浓度远高于产生抗菌效果所需的浓度。最后，酶学研究结果表明，所分析的化合物在主要和次要分子靶标方面表现出与环丙沙星不同的偏好。
• Synthesis and in vitro activity of 1,2,4-triazole-ciprofloxacin hybrids against drug-susceptible and drug-resistant bacteria
  作者：Tomasz Plech、Monika Wujec、Urszula Kosikowska、Anna Malm、Barbara Rajtar、Małgorzata Polz-Dacewicz

  DOI：10.1016/j.ejmech.2012.11.040

  日期：2013.2

  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.