N-cyclohexyl-3-amino-5-oxo-4-phenyl-2,5-dihydro-1H-pyrazole-1-carbothioamide | 1236047-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-cyclohexyl-3-amino-5-oxo-4-phenyl-2,5-dihydro-1H-pyrazole-1-carbothioamide
• 英文别名: 5-amino-N-cyclohexyl-3-oxo-4-phenyl-1H-pyrazole-2-carbothioamide
• CAS: 1236047-74-7
• 化学式: C₁₆H₂₀N₄OS
• 分子量: 316.427
• InChiKey: CGFXVEHTAOWHGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯基氰基乙酸乙酯 在 一水合肼 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 24.0h， 生成 N-cyclohexyl-3-amino-5-oxo-4-phenyl-2,5-dihydro-1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  新型 N-取代-3-氨基-5-氧代-4-苯基-2,5-二氢-1H-吡唑-1-碳硫酰胺的合成、结构和抗菌评价

  摘要：

  通过两种方法合成了新型 N-取代-3-氨基-5-氧代-4-苯基-2,5-二氢-1H-吡唑-1-碳硫酰胺衍生物。第一个是1-(氰基苯基)乙酰基-4-取代氨基硫脲的环化反应，第二个是氰基苯基乙酸酰肼与异硫氰酸酯的反应。新化合物的结构通过元素分析、1H NMR 和 X 射线衍射分析得到证实。生物学评价表明，其中一些具有良好的抗菌活性。© 2010 Wiley Periodicals, Inc. 杂原子化学 21:215–221, 2010; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20598

  DOI：

  10.1002/hc.20598

文献信息

• Inhibitory effect of N-ethyl-3-amino-5-oxo-4-phenyl-2,5-dihydro-1H-pyrazole-1-carbothioamide on Haemophilus spp. planktonic or biofilm-forming cells
  作者：Urszula Kosikowska、Anna Malm、Monika Pitucha、Barbara Rajtar、Malgorzata Polz-Dacewicz

  DOI：10.1007/s00044-013-0700-7

  日期：2014.2

  During this study, we have investigated in vitro activity of N-substituted-3-amino-5-oxo-4-phenyl-2,5-dihydro-1H-pyrazole-1-carbothioamide derivatives with N-ethyl, N-(4-metoxyphenyl) and N-cyclohexyl substituents against Gram-negative Haemophilus influenzae and H. parainfluenzae bacteria. A spectrophotometric assay was used in order to determine the bacterial growth and biofilm formation using a microtiter plate to estimate minimal inhibitory concentration (MIC) and minimal biofilm inhibitory concentration (MBIC). Among the tested N-substituted pyrazole derivatives, only N-ethyl-3-amino-5-oxo-4-phenyl-2,5-dihydro-1H-pyrazole-1-carbothioamide showed a significant in vitro activity against both planktonic cells of H. parainfluenzae (MIC = 0.49-31.25 mu g ml(-1)) and H. influenzae (MIC = 0.24-31.25 mu g ml(-1)) as well as biofilm-forming cells of H. parainfluenzae (MBIC = 0.24-31.25 mu g ml(-1)) and H. influenzae (MBIC = 0.49 to >= 31.25 mu g ml(-1)). The pyrazole compound exerted higher inhibitory effect both on the growth of planktonic cells and biofilm formation by penicillinase-positive and penicillinase-negative isolates of H. parainfluenzae than the activity of commonly used antibiotics such as ampicillin. No cytotoxicity of the tested compound in vitro at concentrations used was found. The tested pyrazole N-ethyl derivative could be considered as a compound for the design of agents active against both pathogenic H. influenzae and opportunistic H. parainfluenzae, showing also anti-biofilm activity. This appears important because biofilms are determinants of bacterial persistence in long-term and recurrent infections recalcitrant to standard therapy.