4-[5-[(E)-2-(5-Chloro-1H-indol-3-yl)-vinyl]-1-(3-chloro-phenyl)-1H-pyrazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester | 721428-27-9

• 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-[5-[(E)-2-(5-Chloro-1H-indol-3-yl)-vinyl]-1-(3-chloro-phenyl)-1H-pyrazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-[5-[(E)-2-(5-chloro-1H-indol-3-yl)ethenyl]-1-(3-chlorophenyl)pyrazol-3-yl]piperidine-1-carboxylate
• CAS: 721428-27-9
• 化学式: C₂₉H₃₀Cl₂N₄O₂
• 分子量: 537.489
• InChiKey: HNGOVMZFGZXPHP-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[5-[(E)-2-(5-Chloro-1H-indol-3-yl)-vinyl]-1-(3-chloro-phenyl)-1H-pyrazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-Chloro-3-{(E)-2-[2-(3-chloro-phenyl)-5-piperidin-4-yl-2H-pyrazol-3-yl]-vinyl}-1H-indole
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of a Novel Series of Potent DNA Gyrase Inhibitors. Pyrazole Derivatives

  摘要：

  We have previously found that a pyrazole derivative 1 possesses antibacterial activity and inhibitory activity against DNA gyrase and topoisomerase TV. Here, we synthesized new pyrazole derivatives and found that 5-[(E)-2-(5-chloroindol-3-yl)vinyl]pyrazole 16 possesses potent antibacterial activity and selective inhibitory activity against bacterial topoisomerases. Many of the synthesized pyrazole derivatives were potent against clinically isolated quinolone- or coumarin-resistant Gram-positive strains and had minimal inhibitory concentration values against these strains equivalent to those against susceptible strains.

  DOI：

  10.1021/jm030394f
• 作为产物：
  描述：

  1-[2-(5-chloroindol-3-yl)]-1-buten-3-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.5h， 生成 4-[5-[(E)-2-(5-Chloro-1H-indol-3-yl)-vinyl]-1-(3-chloro-phenyl)-1H-pyrazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of a Novel Series of Potent DNA Gyrase Inhibitors. Pyrazole Derivatives

  摘要：

  We have previously found that a pyrazole derivative 1 possesses antibacterial activity and inhibitory activity against DNA gyrase and topoisomerase TV. Here, we synthesized new pyrazole derivatives and found that 5-[(E)-2-(5-chloroindol-3-yl)vinyl]pyrazole 16 possesses potent antibacterial activity and selective inhibitory activity against bacterial topoisomerases. Many of the synthesized pyrazole derivatives were potent against clinically isolated quinolone- or coumarin-resistant Gram-positive strains and had minimal inhibitory concentration values against these strains equivalent to those against susceptible strains.

  DOI：

  10.1021/jm030394f