1-[2-(5-chloroindol-3-yl)]-1-buten-3-one | 721428-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[2-(5-chloroindol-3-yl)]-1-buten-3-one
• 英文别名: (E)-4-(5-chloro-1H-indol-3-yl)but-3-en-2-one
• CAS: 721428-12-2
• 化学式: C₁₂H₁₀ClNO
• 分子量: 219.671
• InChiKey: FOVUWYBGNULYBU-NSCUHMNNSA-N

物化性质

• 沸点：
  431.8±30.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[2-(5-chloroindol-3-yl)]-1-buten-3-one 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 30.5h， 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：

  5-氯吲哚-3-甲醛 、 丙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以50%的产率得到1-[2-(5-chloroindol-3-yl)]-1-buten-3-one
  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

文献信息

• Synthesis and antibacterial activity of a novel series of DNA gyrase inhibitors: 5-[(E)-2-arylvinyl]pyrazoles
  作者：Akihiko Tanitame、Yoshihiro Oyamada、Keiko Ofuji、Hideo Terauchi、Motoji Kawasaki、Masaaki Wachi、Jun-ichi Yamagishi

  DOI：10.1016/j.bmcl.2005.06.103

  日期：2005.10

  The 2-arylvinyl moiety in 1-(3-chlorophenyl)-3-(4-piperidyl)-5-[(E)-2-(5-chloro-1H-indol-3-yl)vinyl]pyrazole 2, which has previously shown improved DNA gyrase inhibition and target-related antibacterial activity, was transformed to other groups and the in vitro antibacterial activity of the synthesized compounds was evaluated. Many of the 5-[(E)-2-arylvinyl]pyrazoles synthesized in this study exhibited potent antibacterial activity against quinolone-resistant clinical isolates of Gram-positive bacteria with minimal inhibitory concentration values equivalent to those against susceptible strains. (c) 2005 Elsevier Ltd. All rights reserved.