(E)-6-(5-Chloro-1-methyl-1H-indol-3-yl)-2,4-dioxo-hex-5-enoic acid ethyl ester | 721428-16-6

• 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)-6-(5-Chloro-1-methyl-1H-indol-3-yl)-2,4-dioxo-hex-5-enoic acid ethyl ester
• 英文别名: ethyl (E)-6-(5-chloro-1-methylindol-3-yl)-2,4-dioxohex-5-enoate
• CAS: 721428-16-6
• 化学式: C₁₇H₁₆ClNO₄
• 分子量: 333.771
• InChiKey: JTBZBRUNLMMZGB-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-6-(5-Chloro-1-methyl-1H-indol-3-yl)-2,4-dioxo-hex-5-enoic acid ethyl ester 在 lithium aluminium tetrahydride 、 草酰氯 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 (1R,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 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 (E)-6-(5-Chloro-1-methyl-1H-indol-3-yl)-2,4-dioxo-hex-5-enoic 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

文献信息

• Potent DNA gyrase inhibitors; novel 5-vinylpyrazole analogues with Gram-positive antibacterial activity
  作者：Akihiko Tanitame、Yoshihiro Oyamada、Keiko Ofuji、Kenji Suzuki、Hideaki Ito、Motoji Kawasaki、Masaaki Wachi、Jun-ichi Yamagishi

  DOI：10.1016/j.bmcl.2004.03.045

  日期：2004.6

  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.