(E)-4-(5-Chloro-1-methyl-1H-indol-3-yl)-but-3-en-2-one | 721428-13-3

• 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: (E)-4-(5-Chloro-1-methyl-1H-indol-3-yl)-but-3-en-2-one
• 英文别名: (E)-4-(5-chloro-1-methylindol-3-yl)but-3-en-2-one
• CAS: 721428-13-3
• 化学式: C₁₃H₁₂ClNO
• 分子量: 233.697
• InChiKey: MUFAKPZAUPTJJF-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-4-(5-Chloro-1-methyl-1H-indol-3-yl)-but-3-en-2-one 在 lithium aluminium tetrahydride 、 sodium ethanolate 、 肼 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 生成 {5-[(E)-2-(5-Chloro-1-methyl-1H-indol-3-yl)-vinyl]-1H-pyrazol-3-yl}-methanol
  参考文献：
  名称：

  Potent DNA gyrase inhibitors; novel 5-vinylpyrazole analogues with Gram-positive antibacterial activity

  摘要：

  In this study, we designed and synthesized novel 5-vinylpyrazole analogues by decreasing the lipophilicity of the parent compounds 1a,b; 3-[(3-methoxycarbonyl)cyclohexylaminomethyl]indazoles while keeping the van der Waals interaction with the lipophilic area of DNA gyrase B. The selected compound 8bb exhibited good antibacterial activity against staphylococci and enterococci, including multi-drug resistant strains. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.045
• 作为产物：
  描述：

  丙酮 、 5-chloro-1-methyl-1H-indole-3-carbaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-4-(5-Chloro-1-methyl-1H-indol-3-yl)-but-3-en-2-one
  参考文献：
  名称：

  Potent DNA gyrase inhibitors; novel 5-vinylpyrazole analogues with Gram-positive antibacterial activity

  摘要：

  In this study, we designed and synthesized novel 5-vinylpyrazole analogues by decreasing the lipophilicity of the parent compounds 1a,b; 3-[(3-methoxycarbonyl)cyclohexylaminomethyl]indazoles while keeping the van der Waals interaction with the lipophilic area of DNA gyrase B. The selected compound 8bb exhibited good antibacterial activity against staphylococci and enterococci, including multi-drug resistant strains. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.045

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.