N-[(R)-3-(4-benzhydryl-piperazin-1-yl)-2-hydroxy-propyl]-4-chloro-N-phenethyl-benzenesulfonamide | 1258709-85-1

• 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-[(R)-3-(4-benzhydryl-piperazin-1-yl)-2-hydroxy-propyl]-4-chloro-N-phenethyl-benzenesulfonamide
• 英文别名: N-[(2R)-3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropyl]-4-chloro-N-(2-phenylethyl)benzenesulfonamide
• CAS: 1258709-85-1
• 化学式: C₃₄H₃₈ClN₃O₃S
• 分子量: 604.213
• InChiKey: AVPLNVLKHWYKNZ-JGCGQSQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-1-(4-benzhydryl-piperazin-1-yl)-3-(phenethylamino)-propan-2-ol 、 4-氯苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以0.68 g的产率得到N-[(R)-3-(4-benzhydryl-piperazin-1-yl)-2-hydroxy-propyl]-4-chloro-N-phenethyl-benzenesulfonamide
  参考文献：
  名称：

  BACE1 inhibitory activities of enantiomerically pure, variously substituted N-(3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropyl) arylsulfonamides

  摘要：

  beta-Secretase (BACE1) has been widely recognized as one of the possible therapeutic targets for the treatment of Alzheimer's disease. In this paper, we report the synthesis and the BACE1 inhibitory activity of new, variously substituted N-(3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropyl) arylsulfonamides. Each enantiomeric form was separately evaluated in BACE1 inhibition assays and IC50 values were obtained in the low micromolar range. According to our biological results and docking studies, it can be asserted that the stereochemistry around the OH group in the central hydroxyethylamino linker does not significantly influence the BACE1 inhibitory activity of this type of molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.032

文献信息

• BACE1 inhibitory activities of enantiomerically pure, variously substituted N-(3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropyl) arylsulfonamides
  作者：Simone Bertini、Elisa Ghilardi、Valentina Asso、Carlotta Granchi、Filippo Minutolo、Mauro Pineschi、Valeria Di Bussolo、Andrea Bortolato、Stefano Moro、Alessandro Saba

  DOI：10.1016/j.bmc.2010.09.032

  日期：2010.11.15

  beta-Secretase (BACE1) has been widely recognized as one of the possible therapeutic targets for the treatment of Alzheimer's disease. In this paper, we report the synthesis and the BACE1 inhibitory activity of new, variously substituted N-(3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropyl) arylsulfonamides. Each enantiomeric form was separately evaluated in BACE1 inhibition assays and IC50 values were obtained in the low micromolar range. According to our biological results and docking studies, it can be asserted that the stereochemistry around the OH group in the central hydroxyethylamino linker does not significantly influence the BACE1 inhibitory activity of this type of molecules. (C) 2010 Elsevier Ltd. All rights reserved.