3,4-bis(benzyloxy)-N-piperidin-4-yl-benzamide | 1446498-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-bis(benzyloxy)-N-piperidin-4-yl-benzamide
• 英文别名: 3,4-bis(phenylmethoxy)-N-piperidin-4-ylbenzamide
• CAS: 1446498-66-3
• 化学式: C₂₆H₂₈N₂O₃
• 分子量: 416.52
• InChiKey: NATSIYQFQGIHDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.59
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[5-(benzyloxy)-1H-indol-3-yl]-2-chloroethanone 、 3,4-bis(benzyloxy)-N-piperidin-4-yl-benzamide 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以58%的产率得到3,4-bis(benzyloxy)-N-(1-(2-(5-(benzyloxy)-1H-indol-3-yl)-2-oxoethyl)piperidin-4-yl)benzamide
  参考文献：
  名称：

  Indole derivatives as dual-effective agents for the treatment of neurodegenerative diseases: Synthesis, biological evaluation, and molecular modeling studies

  摘要：

  Several indole derivatives, that were highly potent ligands of GluN2B-subunit-containing N-methyl-D-aspartate (NMDA) receptor, also demonstrated antioxidant properties in ABTS method. In particular, the 2-(4-benzylpiperidin-1-yl)-1-(5-hydroxy-1H-indol-3-yl)ethanone (1) proved to be a dual-effective neuroprotective agent. With the aim to increase the antioxidant properties we added a catechol moiety onto piperidine moiety. The designed hybrid derivative 3,4-dihydroxy-N-[1-[2-(5-hydroxy-1H-indol-3-yl)-2-oxoethyl]piperidin-4-yl]benzamide (10) was the most effective antioxidant agent (>94.1 +/- 0.1% of inhibition at 17 mu M) and showed GluN2B/NMDA receptor affinity at low micromolar concentration (IC50 0.66 mu M). By means of computational studies we explored the effect of the presence of this antioxidant fragment during the recognition process to binding pocket. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.044
• 作为产物：
  描述：

  原儿茶酸 在 4-二甲氨基吡啶 、 potassium carbonate 、 1-羟基苯并三唑 、 1,2-二氯乙烷 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 3,4-bis(benzyloxy)-N-piperidin-4-yl-benzamide
  参考文献：
  名称：

  Indole derivatives as dual-effective agents for the treatment of neurodegenerative diseases: Synthesis, biological evaluation, and molecular modeling studies

  摘要：

  Several indole derivatives, that were highly potent ligands of GluN2B-subunit-containing N-methyl-D-aspartate (NMDA) receptor, also demonstrated antioxidant properties in ABTS method. In particular, the 2-(4-benzylpiperidin-1-yl)-1-(5-hydroxy-1H-indol-3-yl)ethanone (1) proved to be a dual-effective neuroprotective agent. With the aim to increase the antioxidant properties we added a catechol moiety onto piperidine moiety. The designed hybrid derivative 3,4-dihydroxy-N-[1-[2-(5-hydroxy-1H-indol-3-yl)-2-oxoethyl]piperidin-4-yl]benzamide (10) was the most effective antioxidant agent (>94.1 +/- 0.1% of inhibition at 17 mu M) and showed GluN2B/NMDA receptor affinity at low micromolar concentration (IC50 0.66 mu M). By means of computational studies we explored the effect of the presence of this antioxidant fragment during the recognition process to binding pocket. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.044

文献信息

• PENAM DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  申请人：TenNor Therapeutics Limited

  公开号：US20210070774A1

  公开（公告）日：2021-03-11

  Novel iron chelating group conjugated penam derivatives described herein show antibacterial activity, and could be used as antibacterial agents or beta-lactamase inhibitors (BLIs) which are of value for application in combination with other antibacterial agents.

  本文描述的新型铁螯合基团共轭的青霉素衍生物表现出抗菌活性，可用作抗菌剂或β-内酰胺酶抑制剂（BLIs），与其他抗菌剂联合应用具有价值。
• Penam derivatives for treating bacterial infections
  申请人：TenNor Therapeutics Limited

  公开号：US11040987B2

  公开（公告）日：2021-06-22

  Novel iron chelating group conjugated penam derivatives described herein show antibacterial activity, and could be used as antibacterial agents or beta-lactamase inhibitors (BLIs) which are of value for application in combination with other antibacterial agents.

  本文所述的新型铁螯合基团共轭五氯化萘衍生物具有抗菌活性，可用作抗菌剂或β-内酰胺酶抑制剂（BLIs），具有与其他抗菌剂联合应用的价值。