methyl 1-(1-acetyl-1H-indol-3-yl)-9-(2-(trifluoromethyl)benzyl)-9H-pyrido[3,4-b]indole-3-carboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: methyl 1-(1-acetyl-1H-indol-3-yl)-9-(2-(trifluoromethyl)benzyl)-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: Methyl 1-(1-acetylindol-3-yl)-9-[[2-(trifluoromethyl)phenyl]methyl]pyrido[3,4-b]indole-3-carboxylate；methyl 1-(1-acetylindol-3-yl)-9-[[2-(trifluoromethyl)phenyl]methyl]pyrido[3,4-b]indole-3-carboxylate
• 化学式: C₃₁H₂₂F₃N₃O₃
• 分子量: 541.529
• InChiKey: HTIFAYRMMKELMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 1-(1-acetyl-1H-indol-3-yl)-9-(2-(trifluoromethyl)benzyl)-9H-pyrido[3,4-b]indole-3-carboxylate 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以83%的产率得到(1-(1H-indol-3-yl)-9-(2-(trifluoromethyl)benzyl)-9H-pyrido[3,4-b]indol-3-yl)methanol
  参考文献：
  名称：

  Computer-aided drug discovery: Novel 3,9-disubstituted eudistomin U derivatives as potent antibacterial agents

  摘要：

  Thirty-two new 3,9-disubstituted eudistomin U derivatives were designed and synthesized based on computer-aided drug discovery (CADD). Sixteen 3,9-disubstituted eudistomin U derivatives (6a-6p) have exhibited potent antibacterial activity. Specially, the most active compound 6p displayed better activity than commercial drugs fosfomycin sodium, ciprofloxacin and propineb, with a peak minimum inhibitory concentration (MIC) of 1.5625 mu mol/L. The antibacterial mechanism indicated that these compounds could exert bactericidal effect by damaging bacterial cell membrane and disrupting the function of DNA gyrase. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.001
• 作为产物：
  描述：

  N-乙酰基吲哚-3-甲醛 在 palladium 10% on activated carbon 、 氧气 、 potassium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 甲苯 、 乙腈 为溶剂， 反应 76.0h， 生成 methyl 1-(1-acetyl-1H-indol-3-yl)-9-(2-(trifluoromethyl)benzyl)-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Computer-aided drug discovery: Novel 3,9-disubstituted eudistomin U derivatives as potent antibacterial agents

  摘要：

  Thirty-two new 3,9-disubstituted eudistomin U derivatives were designed and synthesized based on computer-aided drug discovery (CADD). Sixteen 3,9-disubstituted eudistomin U derivatives (6a-6p) have exhibited potent antibacterial activity. Specially, the most active compound 6p displayed better activity than commercial drugs fosfomycin sodium, ciprofloxacin and propineb, with a peak minimum inhibitory concentration (MIC) of 1.5625 mu mol/L. The antibacterial mechanism indicated that these compounds could exert bactericidal effect by damaging bacterial cell membrane and disrupting the function of DNA gyrase. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.001

文献信息

• Computer-aided drug discovery: Novel 3,9-disubstituted eudistomin U derivatives as potent antibacterial agents
  作者：Jiangkun Dai、Wenjia Dan、Na Li、Junru Wang

  DOI：10.1016/j.ejmech.2018.08.001

  日期：2018.9

  Thirty-two new 3,9-disubstituted eudistomin U derivatives were designed and synthesized based on computer-aided drug discovery (CADD). Sixteen 3,9-disubstituted eudistomin U derivatives (6a-6p) have exhibited potent antibacterial activity. Specially, the most active compound 6p displayed better activity than commercial drugs fosfomycin sodium, ciprofloxacin and propineb, with a peak minimum inhibitory concentration (MIC) of 1.5625 mu mol/L. The antibacterial mechanism indicated that these compounds could exert bactericidal effect by damaging bacterial cell membrane and disrupting the function of DNA gyrase. (C) 2018 Elsevier Masson SAS. All rights reserved.