3-[(3R,5S)-2-oxo-5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]oxolan-3-yl]propanoic acid | 674787-23-6

• 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: 3-[(3R,5S)-2-oxo-5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]oxolan-3-yl]propanoic acid
• CAS: 674787-23-6
• 化学式: C₂₃H₂₅NO₆
• 分子量: 411.455
• InChiKey: TZNAUNSAFYWTOT-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(3R,5S)-2-oxo-5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]oxolan-3-yl]propanoic acid 在 palladium on activated charcoal 哌啶 、 N-甲基吗啉 、 2-羟基吡啶 、 乙二胺四乙酸 、 硫酸 、 氢气 、 1-羟基苯并三唑 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 162.17h， 生成 (4R,6S,7S)-7-[(S)-3-Carboxy-3-(3-methyl-butyrylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid
  参考文献：
  名称：

  Rational design and synthesis of selective BACE-1 inhibitors

  摘要：

  An effective approach for enhancing the selectivity of beta-site amyloid precursor protein cleaving enzyme (BACE 1) inhibitors is developed based on the unique features of the S1' pocket of the enzyme. A series of low molecular weight ( < 600) compounds were synthesized with different moieties at the P1' position. The selectivity of BACE 1 inhibitors versus cathepsin D and renin was enhanced 120-fold by replacing the hydrophobic propyl group with a hydrophilic propionic acid group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.061
• 作为产物：
  描述：

  phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate 在 ruthenium trichloride 、 sodium periodate 、 3> 、 lithium hexamethyldisilazane 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 四氯化碳 、 乙腈 为溶剂， 反应 16.0h， 生成 3-[(3R,5S)-2-oxo-5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]oxolan-3-yl]propanoic acid
  参考文献：
  名称：

  Rational design and synthesis of selective BACE-1 inhibitors

  摘要：

  An effective approach for enhancing the selectivity of beta-site amyloid precursor protein cleaving enzyme (BACE 1) inhibitors is developed based on the unique features of the S1' pocket of the enzyme. A series of low molecular weight ( < 600) compounds were synthesized with different moieties at the P1' position. The selectivity of BACE 1 inhibitors versus cathepsin D and renin was enhanced 120-fold by replacing the hydrophobic propyl group with a hydrophilic propionic acid group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.061

文献信息

• Rational design and synthesis of selective BACE-1 inhibitors
  作者：Stephen F. Brady、Satendra Singh、Ming-Chih Crouthamel、M.Katharine Holloway、Craig A. Coburn、Victor M. Garsky、Michael Bogusky、Michael W. Pennington、Joseph P. Vacca、Daria Hazuda、Ming-Tain Lai

  DOI：10.1016/j.bmcl.2003.11.061

  日期：2004.2

  An effective approach for enhancing the selectivity of beta-site amyloid precursor protein cleaving enzyme (BACE 1) inhibitors is developed based on the unique features of the S1' pocket of the enzyme. A series of low molecular weight ( < 600) compounds were synthesized with different moieties at the P1' position. The selectivity of BACE 1 inhibitors versus cathepsin D and renin was enhanced 120-fold by replacing the hydrophobic propyl group with a hydrophilic propionic acid group. (C) 2003 Elsevier Ltd. All rights reserved.