methyl 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoate | 287935-86-8

• 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: methyl 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoate
• CAS: 287935-86-8
• 化学式: C₂₁H₂₆NO₆P
• 分子量: 419.414
• InChiKey: CIMSUXUYCPBHRP-VTBWFHPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoate 在 sodium hydroxide 、 三溴化硼 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 (S)-2-{(S)-3-[((R)-1-Amino-ethyl)-hydroxy-phosphinoyl]-2-benzyl-propionylamino}-3-phenyl-propionic acid
  参考文献：
  名称：

  Design of the first highly potent and selective aminopeptidase N (EC 3.4.11.2) inhibitor

  摘要：

  A series of phosphinic compounds mimicking the transition state of substrates hydrolysed by aminopeptidase N (EC 3.4.11.2) were synthesized. These new compounds have potent inhibitory activities with Ki values in the nanomolar range. These derivatives behave as the most potent APN inhibitors designed to date.

  DOI：

  10.1016/s0960-894x(99)00219-x
• 作为产物：
  描述：

  benzyloxycarbonyl-1-aminoethyl-1-phosphinate 在 N,O-双三甲硅基乙酰胺 作用下， 生成 methyl 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoate
  参考文献：
  名称：

  Design of the first highly potent and selective aminopeptidase N (EC 3.4.11.2) inhibitor

  摘要：

  A series of phosphinic compounds mimicking the transition state of substrates hydrolysed by aminopeptidase N (EC 3.4.11.2) were synthesized. These new compounds have potent inhibitory activities with Ki values in the nanomolar range. These derivatives behave as the most potent APN inhibitors designed to date.

  DOI：

  10.1016/s0960-894x(99)00219-x

文献信息

• Synthesis of 2(S)-benzyl-3-[hydroxy(1?(R)-amino ethyl)phosphinyl]propanoyl-L-3-[125I]-iodotyrosine: a radiolabelled inhibitor of aminopeptidase N
  作者：Huixiong Chen、Laurent Bischoff、Marie-Claude Fournie-Zaluski、Bernard P. Roques

  DOI：10.1002/(sici)1099-1344(200002)43:2<103::aid-jlcr294>3.0.co;2-i

  日期：2000.2

  2(S)-benzyl-3-[hydroxy(1′(R)-aminoethyl)phosphinyl]propanoyl-L-3-[125I]-iodo tyrosine was prepared from 1(R)-(N-benzyloxycarbonylamino)ethylphosphinic acid in a six step synthesis. This new iodinated compound, which is a highly efficient aminopeptidase N inhibitor (Ki=0·95 nM), can be used for complete characterization of the biochemical and pharmacological properties of aminopeptidase N and its in

  2(S)-苄基-3-[羟基(1'(R)-氨基乙基)膦基]丙酰基-L-3-[125I]-碘酪氨酸由1(R)-(N-苄氧基羰基氨基)乙基次膦酸制备六步合成。这种新型碘化化合物是一种高效的氨肽酶 N 抑制剂 (Ki=0·95 nM)，可用于完整表征氨肽酶 N 的生化和药理特性及其体内抑制作用。在合成结束时获得高放射化学纯度，比活为 217 Ci/mmol。版权所有 © 2000 John Wiley & Sons, Ltd.