4-((4-(1H-indol-3-yl)piperidin-1-yl)methyl)benzaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-((4-(1H-indol-3-yl)piperidin-1-yl)methyl)benzaldehyde
• 英文别名: 4-[[4-(1H-indol-3-yl)piperidin-1-yl]methyl]benzaldehyde
• 化学式: C₂₁H₂₂N₂O
• 分子量: 318.418
• InChiKey: INPUKMHZGJTQNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((4-(1H-indol-3-yl)piperidin-1-yl)methyl)benzaldehyde 、 3-(4’-哌啶基)-1H-吲哚 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以30%的产率得到1,4-bis((4-(1H-indol-3-yl)piperidin-1-yl)methyl)benzene
  参考文献：
  名称：

  Exploring the 3-piperidin-4-yl-1H-indole scaffold as a novel antimalarial chemotype

  摘要：

  A series of 3-piperidin-4-yl-1H-indoles with building block diversity was synthesized based on a hit derived from an HTS whole-cell screen against Plasmodium falciparum. Thirty-eight compounds were obtained following a three-step synthetic approach and evaluated for anti-parasitic activity. The SAR shows that 3-piperidin-4-yl-1H-indole is intolerant to most N-piperidinyl modifications. Nevertheless, we were able to identify a new compound (10d) with lead-like properties (MW = 305; cLogP = 2.42), showing antimalarial activity against drug-resistant and sensitive strains (EC50 values similar to 3 mu M), selectivity for malaria parasite and no cross-resistance with chloroquine, thus representing a potential new chemotype for further optimization towards novel and affordable antimalarial drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.047
• 作为产物：
  描述：

  3-(1-苄基-1,2,3,6-四氢吡啶-4-基)-1H-吲哚 在 palladium 10% on activated carbon 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 4-((4-(1H-indol-3-yl)piperidin-1-yl)methyl)benzaldehyde
  参考文献：
  名称：

  Exploring the 3-piperidin-4-yl-1H-indole scaffold as a novel antimalarial chemotype

  摘要：

  A series of 3-piperidin-4-yl-1H-indoles with building block diversity was synthesized based on a hit derived from an HTS whole-cell screen against Plasmodium falciparum. Thirty-eight compounds were obtained following a three-step synthetic approach and evaluated for anti-parasitic activity. The SAR shows that 3-piperidin-4-yl-1H-indole is intolerant to most N-piperidinyl modifications. Nevertheless, we were able to identify a new compound (10d) with lead-like properties (MW = 305; cLogP = 2.42), showing antimalarial activity against drug-resistant and sensitive strains (EC50 values similar to 3 mu M), selectivity for malaria parasite and no cross-resistance with chloroquine, thus representing a potential new chemotype for further optimization towards novel and affordable antimalarial drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.047