(2R,3S,1'R)-3-(t-Boc-amino)-2-hydroxy-4-phenyl-1-<(1-phenylethyl)amino>butane | 98737-30-5

• 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: (2R,3S,1'R)-3-(t-Boc-amino)-2-hydroxy-4-phenyl-1-<(1-phenylethyl)amino>butane
• 英文别名: tert-butyl ((2S,3R)-3-hydroxy-1-phenyl-4-(((R)-1-phenylethyl)amino)butan-2-yl)carbamate；[(1S,2R)-1-benzyl-2-hydroxy-3-[(R)-1-phenyl-ethylamino]-propyl]-carbamic acid tert-butyl ester；Carbamic acid, [(1S,2R)-2-hydroxy-3-[[(1R)-1-phenylethyl]amino]-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester；tert-butyl N-[(2S,3R)-3-hydroxy-1-phenyl-4-[[(1R)-1-phenylethyl]amino]butan-2-yl]carbamate
• CAS: 98737-30-5
• 化学式: C₂₃H₃₂N₂O₃
• 分子量: 384.519
• InChiKey: UEJADZVUJDDOFT-JRGCBEDISA-N

物化性质

• 沸点：
  546.2±50.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  70.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,1'R)-3-(t-Boc-amino)-2-hydroxy-4-phenyl-1-<(1-phenylethyl)amino>butane 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 3-(azepane-1-carbonyl)-N-[(2S,3R)-3-hydroxy-1-phenyl-4-[[(1R)-1-phenylethyl]amino]butan-2-yl]benzamide
  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：

  N-Boc-L-苯丙氨醛 以 四氢呋喃 、 异丙醇 为溶剂， 反应 5.5h， 生成 (2R,3S,1'R)-3-(t-Boc-amino)-2-hydroxy-4-phenyl-1-<(1-phenylethyl)amino>butane
  参考文献：
  名称：

  A stereocontrolled synthesis of hydroxyethylene dipeptide isosteres using novel, chiral aminoalkyl epoxides and .gamma.-(aminoalkyl)-.gamma.-lactones

  摘要：

  DOI：

  10.1021/jo00223a037

文献信息

• Substrate Peptidomimetic Inhibitors of <i>P. falciparum</i> Plasmepsin X with Potent Antimalarial Activity
  作者：Lachlan W. Richardson、Trent D. Ashton、Madeline G. Dans、Nghi Nguyen、Paola Favuzza、Tony Triglia、Anthony N. Hodder、Anna Ngo、Kate E. Jarman、Alan F. Cowman、Brad E. Sleebs

  DOI：10.1002/cmdc.202200306

  日期：2022.9.16

  Substrate mimicry: Substrate peptidomimetics were designed and showed potent inhibition of plasmepsin X (PMX). The peptidomimetics block PMX ligand processing, arrest asexual parasites at the schizont stage and potently kill P. falciparum parasites. The peptidomimetics will further assist in the understanding of PMX selectivity and in the development of PMX targeted antimalarials.

  底物拟态：设计了底物拟肽并显示出对血浆蛋白酶 X (PMX) 的有效抑制作用。肽模拟物阻断 PMX 配体加工，在裂殖体阶段阻止无性寄生虫并有效杀死恶性疟原虫寄生虫。肽模拟物将进一步帮助理解 PMX 选择性和开发 PMX 靶向抗疟药。
• Aspartic protease inhibitors via C1-homologation of peptidic aldehydes and studies on reduced amide isosteres
  作者：Hannes A. Braun、Andrea Zall、Manfred Brockhaus、Marco Schütz、Reinhard Meusinger、Boris Schmidt

  DOI：10.1016/j.tetlet.2007.09.047

  日期：2007.11

  (R)-Configured isophthalic hydroxyethylamines play an important role in the inhibition of beta-secretase (BACE1). We present the synthesis of a number of (S)-configured hydroxyethylamine derivatives via 2-iodoethanol intermediates and the comparison with the (R)-analogues. An N-substituted indole was investigated as a substitute for the isophthalamide moiety. (c) 2007 Elsevier Ltd. 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.
• A stereocontrolled synthesis of hydroxyethylene dipeptide isosteres using novel, chiral aminoalkyl epoxides and .gamma.-(aminoalkyl)-.gamma.-lactones
  作者：Ben E. Evans、Kenneth E. Rittle、Carl F. Homnick、James P. Springer、Jordan Hirshfield、Daniel F. Veber

  DOI：10.1021/jo00223a037

  日期：1985.11