N-(3-carbazol-9-yl-2-hydroxypropyl)-N-(4-nitrophenyl)benzamide | 1345853-35-1

• 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: N-(3-carbazol-9-yl-2-hydroxypropyl)-N-(4-nitrophenyl)benzamide
• CAS: 1345853-35-1
• 化学式: C₂₈H₂₃N₃O₄
• 分子量: 465.508
• InChiKey: NEQSBPZDCBNIIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9-(环氧-2-甲基)-9H-咔唑 在 4-二甲氨基吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-(3-carbazol-9-yl-2-hydroxypropyl)-N-(4-nitrophenyl)benzamide
  参考文献：
  名称：

  Carbazole-containing arylcarboxamides as BACE1 inhibitors

  摘要：

  beta-Secretase (BACE1) is widely recognized as a prime drug target for the treatment of Alzheimer's disease (AD). In this Letter, we report the synthesis and the BACE1 inhibitory activity of novel, variously substituted N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-arylcarboxamides. The best results have been obtained with the introduction of a 4-OMe substituent (IC50 = 3.8 mu M) or a 3,4-dichloro substituent (IC50 = 2.5 mu M) in the amidic aromatic ring. The blood-brain barrier penetration predictions resulted to be promising for this type of compounds. To better understand the structure-activity relationships (SAR) of the new derivatives, a docking study procedure has been applied exploiting different conformational and ionic states of BACE1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.064

文献信息

• Carbazole-containing arylcarboxamides as BACE1 inhibitors
  作者：Simone Bertini、Valentina Asso、Elisa Ghilardi、Carlotta Granchi、Clementina Manera、Filippo Minutolo、Giuseppe Saccomanni、Andrea Bortolato、Jonathan Mason、Stefano Moro、Marco Macchia

  DOI：10.1016/j.bmcl.2011.09.064

  日期：2011.11

  beta-Secretase (BACE1) is widely recognized as a prime drug target for the treatment of Alzheimer's disease (AD). In this Letter, we report the synthesis and the BACE1 inhibitory activity of novel, variously substituted N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-arylcarboxamides. The best results have been obtained with the introduction of a 4-OMe substituent (IC50 = 3.8 mu M) or a 3,4-dichloro substituent (IC50 = 2.5 mu M) in the amidic aromatic ring. The blood-brain barrier penetration predictions resulted to be promising for this type of compounds. To better understand the structure-activity relationships (SAR) of the new derivatives, a docking study procedure has been applied exploiting different conformational and ionic states of BACE1. (C) 2011 Elsevier Ltd. All rights reserved.