5-[(E)-2-(5-Chloro-1-methyl-1H-indol-3-yl)-vinyl]-1H-pyrazole-3-carboxylic acid ethyl ester | 721428-18-8

• 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: 5-[(E)-2-(5-Chloro-1-methyl-1H-indol-3-yl)-vinyl]-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5-[(E)-2-(5-chloro-1-methylindol-3-yl)ethenyl]-1H-pyrazole-3-carboxylate
• CAS: 721428-18-8
• 化学式: C₁₇H₁₆ClN₃O₂
• 分子量: 329.786
• InChiKey: HCTBQVYQOWWMQV-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(E)-2-(5-Chloro-1-methyl-1H-indol-3-yl)-vinyl]-1H-pyrazole-3-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 、 草酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 (1S,3R)-3-({5-[(Z)-2-(5-Chloro-1-methyl-1H-indol-3-yl)-vinyl]-1H-pyrazol-3-ylmethyl}-amino)-cyclohexanecarboxylic acid methyl ester
  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：

  5-chloro-1-methyl-1H-indole-3-carbaldehyde 在 sodium hydroxide 、 sodium ethanolate 、 肼 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 5-[(E)-2-(5-Chloro-1-methyl-1H-indol-3-yl)-vinyl]-1H-pyrazole-3-carboxylic acid ethyl ester
  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