(2S)-2-<(tert-butoxycarbonyl)amino>-3-(1-naphthyl)-1-propanol | 148745-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S)-2-<(tert-butoxycarbonyl)amino>-3-(1-naphthyl)-1-propanol
• 英文别名: tert-butyl (S)-(1-hydroxy-3-(naphthalen-1-yl)propan-2-yl)carbamate；tert-butyl N-[(2S)-1-hydroxy-3-naphthalen-1-ylpropan-2-yl]carbamate
• CAS: 148745-10-2
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: HXKBMNNMOIOUJR-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-<(tert-butoxycarbonyl)amino>-3-(1-naphthyl)-1-propanol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以71%的产率得到Boc-3-(1-萘基)-L-丙氨酸
  参考文献：
  名称：

  Synthesis of N-Boc-β-Aryl Alanines and of N-Boc-β-Methyl-β-aryl Alanines by Regioselective Ring-Opening of Enantiomerically Pure N-Boc-Aziridines

  摘要：

  DOI：

  10.1021/jo981140i
• 作为产物：
  描述：

  Boc-3-(1-萘基)-L-丙氨酸 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-2-<(tert-butoxycarbonyl)amino>-3-(1-naphthyl)-1-propanol
  参考文献：
  名称：

  Potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme identified in rat lung

  摘要：

  Two structurally distinct series of potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme (ECE) activity identified in the rat lung have been developed. Pepstatin A, which potently inhibits the rat lung ECE, served as the basis for the first series. Alternatively, selected renin inhibitors containing the dihydroxyethylene moiety were shown to be inhibitors of rat lung activity. Subsequent modifications improved inhibition of the rat lung ECE while eliminating renin activity. Both series of ECE inhibitors demonstrated a range of selectivity over Cathepsin D. Water-solubilizing moieties were appended onto selected compounds to facilitate in vivo testing. Partial reduction of the pressor response to exogenously administered Big ET-1 was observed with selected rat lung ECE inhibitors.

  DOI：

  10.1021/jm00056a007

文献信息

• BIMP‐Catalyzed 1,3‐Prototropic Shift for the Highly Enantioselective Synthesis of Conjugated Cyclohexenones
  作者：Jonathan C. Golec、Eve M. Carter、John W. Ward、William G. Whittingham、Luis Simón、Robert S. Paton、Darren J. Dixon

  DOI：10.1002/anie.202006202

  日期：2020.9.28

  A bifunctional iminophosphorane (BIMP)‐catalysed enantioselective synthesis of α,β‐unsaturated cyclohexenones through a facially selective 1,3‐prototropic shift of β,γ‐unsaturated prochiral isomers, under mild reaction conditions and in short reaction times, on a range of structurally diverse substrates, is reported. α,β‐Unsaturated cyclohexenone products primed for downstream derivatisation were obtained

  双功能亚氨基正膦 (BIMP) 催化对映选择性合成 α,β-不饱和环己烯酮，通过 β,γ-不饱和前手性异构体的表面选择性 1,3-质子转移，在温和的反应条件和短的反应时间内，在一系列据报道，结构多样的底物。用于下游衍生化的 α,β-不饱和环己烯酮产品以高收率（高达 99%）和一致的高对映选择性（高达 99% ee ）获得。对反应机理和对映选择性起源（包括 TS 能量的多元线性回归）进行了计算研究，发现所得数据与实验结果非常吻合。
• Potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme identified in rat lung
  作者：Kazumi Shiosaki、Andrew S. Tasker、Gerard M. Sullivan、Bryan K. Sorensen、Thomas W. von Geldern、Jinshyun R. Wu-Wong、Carol A. Marselle、Terry J. Opgenorth

  DOI：10.1021/jm00056a007

  日期：1993.2

  Two structurally distinct series of potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme (ECE) activity identified in the rat lung have been developed. Pepstatin A, which potently inhibits the rat lung ECE, served as the basis for the first series. Alternatively, selected renin inhibitors containing the dihydroxyethylene moiety were shown to be inhibitors of rat lung activity. Subsequent modifications improved inhibition of the rat lung ECE while eliminating renin activity. Both series of ECE inhibitors demonstrated a range of selectivity over Cathepsin D. Water-solubilizing moieties were appended onto selected compounds to facilitate in vivo testing. Partial reduction of the pressor response to exogenously administered Big ET-1 was observed with selected rat lung ECE inhibitors.
• Discovery of trans-3,4′-bispyridinylethylenes as potent and novel inhibitors of protein kinase B (PKB/Akt) for the treatment of cancer: Synthesis and biological evaluation
  作者：Qun Li、Tongmei Li、Gui-Dong Zhu、Jianchun Gong、Akiyo Claibone、Chris Dalton、Yan Luo、Eric F. Johnson、Yan Shi、Xuesong Liu、Vered Klinghofer、Joy L. Bauch、Kennan C. Marsh、Jennifer J. Bouska、Shannon Arries、Ron De Jong、Tilman Oltersdorf、Vincent S. Stoll、Clarissa G. Jakob、Saul H. Rosenberg、Vincent L. Giranda

  DOI：10.1016/j.bmcl.2005.12.017

  日期：2006.3

  A novel series of Akt/PKB inhibitors derived from a screening lead (1) has been prepared. The novel trans-3,4'-bispyridinylethylenes described herein are potent inhibitors of Akt/PKB with IC50 values in the low double-digit nanomolar range against Akt1. Compound 2q shows excellent selectivity against distinct families of kinases such as tyrosine kinases and CAMK, and displays poor to modest selectivity against closely related kinases in the AGC and CMGC families. The cellular activities including inhibition of cell growth and phosphorylation of downstream target GSK3 are also described. The X-ray structure of compound 2q complexed with PKA in the ATP binding site was determined. (C) 2005 Elsevier Ltd. All rights reserved.
• Identification of a novel 3,5-disubstituted pyridine as a potent, selective, and orally active inhibitor of Akt1 kinase
  作者：Sheela A. Thomas、Tongmei Li、Keith W. Woods、Xiaohong Song、Garrick Packard、John P. Fischer、Robert B. Diebold、Xuesong Liu、Yan Shi、Vered Klinghofer、Eric F. Johnson、Jennifer J. Bouska、Amanda Olson、Ran Guan、Shayna R. Magnone、Kennan Marsh、Yan Luo、Saul H. Rosenberg、Vincent L. Giranda、Qun Li

  DOI：10.1016/j.bmcl.2006.04.046

  日期：2006.7

  Based on lead compounds 2 and 3 a series of 3,5-disubstituted pyridines have been designed and evaluated for inhibition of AKT/PKB. Modifications at the 3 position of the pyridine ring led to a number of potent compounds with improved physical properties, resulting in the identification of 11g as a promising, orally active Akt inhibitor. The synthesis, structure-activity relationship studies, and pharmacokinetic data are presented in this paper. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of <i>N</i>-Boc-β-Aryl Alanines and of <i>N</i>-Boc-β-Methyl-β-aryl Alanines by Regioselective Ring-Opening of Enantiomerically Pure <i>N</i>-Boc-Aziridines
  作者：Eva Medina、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/jo981140i

  日期：1998.11.1