tert-butyl N-[(2S,3R)-4-(4-benzylpiperazin-1-yl)-3-hydroxy-1-phenylbutan-2-yl]carbamate | 1146971-35-8

• 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: tert-butyl N-[(2S,3R)-4-(4-benzylpiperazin-1-yl)-3-hydroxy-1-phenylbutan-2-yl]carbamate
• CAS: 1146971-35-8
• 化学式: C₂₆H₃₇N₃O₃
• 分子量: 439.598
• InChiKey: RADKAYOXSIZUCF-BJKOFHAPSA-N

物化性质

• 熔点：
  96-98 °C(Solvent: Methanol; Water)
• 沸点：
  595.4±50.0 °C(predicted)
• 密度：
  1.123±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S,3R)-4-(4-benzylpiperazin-1-yl)-3-hydroxy-1-phenylbutan-2-yl]carbamate 在 N-乙基吗啉 、 盐酸 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 1-N-[(2S,3R)-4-(4-benzylpiperazin-1-yl)-3-hydroxy-1-phenylbutan-2-yl]-3-N,3-N-dipropylbenzene-1,3-dicarboxamide
  参考文献：
  名称：

  Novel in vivo active anti-malarials based on a hydroxy-ethyl-amine scaffold

  摘要：

  A novel series of anti-malarials, based on a hydroxy-ethyl-amine scaffold, initially identified as peptidomimetic protease inhibitors is described. Combination of the hydroxy-ethyl-amine anti-malarial phramacophore with the known Mannich base pharmacophore of amodiaquine (57) resulted in promising in vivo active novel derivatives. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.118
• 作为产物：
  描述：

  1-苄基哌嗪 、 1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯 以 甲醇 为溶剂， 反应 48.0h， 生成 tert-butyl N-[(2S,3R)-4-(4-benzylpiperazin-1-yl)-3-hydroxy-1-phenylbutan-2-yl]carbamate
  参考文献：
  名称：

  Novel in vivo active anti-malarials based on a hydroxy-ethyl-amine scaffold

  摘要：

  A novel series of anti-malarials, based on a hydroxy-ethyl-amine scaffold, initially identified as peptidomimetic protease inhibitors is described. Combination of the hydroxy-ethyl-amine anti-malarial phramacophore with the known Mannich base pharmacophore of amodiaquine (57) resulted in promising in vivo active novel derivatives. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.118

文献信息

• Synthesis, antimalarial evaluation and molecular modeling studies of hydroxyethylpiperazines, potential aspartyl protease inhibitors, Part 2
  作者：Wilson Cunico、Claudia R.B. Gomes、Victor Facchinetti、Marcele Moreth、Carmen Penido、Maria G.M.O. Henriques、Fernando P. Varotti、Luisa G. Krettli、Antoniana U. Krettli、Franklin S. da Silva、Ernesto R. Caffarena、Camila S. de Magalhães

  DOI：10.1016/j.ejmech.2009.03.041

  日期：2009.9

  The antimalarial acitivity of hydroxyethylamines, synthesized from the reaction of intermediated hydroxyethypiperazines with benzenesulfonyl chlorides or benzoyl chlorides, has been evaluated in vitro against a W2 Plasmodium falciparum clone. Some of the nineteen tested derivatives showed a significant activity in vitro, thus turning into a promising new class of antimalarials. In addition, a molecular modeling study of the most active derivative (51) was performed and its most probable binding modes within plasmepsin II enzyme were identified. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis and antimalarial activity of hydroxyethylpiperazine derivatives
  作者：Wilson Cunico、Claudia R.B. Gomes、Marcele Moreth、Diogo P. Manhanini、Isabela H. Figueiredo、Carmen Penido、Maria G.M.O. Henriques、Fernando P. Varotti、Antoniana U. Krettli

  DOI：10.1016/j.ejmech.2008.04.009

  日期：2009.3

  The antimalarial activity of hydroxyethylpiperazine derivatives, synthesized from the reaction of (2S,3S)Boc-phenylaianine epoxide with benzylpiperazines in good yields (76-96%), has been evaluated in vitro against the Plasmodium falciparum W2 clone (chloroquine resistant). The results show that some compounds have moderate activity against this parasite and none of the active compounds showed cytotoxicity at high concentration (100 mu g/ml). (C) 2008 Elsevier Masson SAS. All rights reserved.
• Novel in vivo active anti-malarials based on a hydroxy-ethyl-amine scaffold
  作者：Claire-Lise Ciana、Romain Siegrist、Hamed Aissaoui、Léo Marx、Sophie Racine、Solange Meyer、Christoph Binkert、Ruben de Kanter、Christoph Fischli、Sergio Wittlin、Christoph Boss

  DOI：10.1016/j.bmcl.2012.11.118

  日期：2013.2

  A novel series of anti-malarials, based on a hydroxy-ethyl-amine scaffold, initially identified as peptidomimetic protease inhibitors is described. Combination of the hydroxy-ethyl-amine anti-malarial phramacophore with the known Mannich base pharmacophore of amodiaquine (57) resulted in promising in vivo active novel derivatives. (c) 2012 Elsevier Ltd. All rights reserved.