Benzyl 1-(Bis(3,4-Dimethylphenoxy)Phosphoryl)Propylcarbamate | 1402801-67-5

• 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: Benzyl 1-(Bis(3,4-Dimethylphenoxy)Phosphoryl)Propylcarbamate
• 英文别名: benzyl N-[1-bis(3,4-dimethylphenoxy)phosphorylpropyl]carbamate
• CAS: 1402801-67-5
• 化学式: C₂₇H₃₂NO₅P
• 分子量: 481.529
• InChiKey: JEGWYPUVNAIJFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl 1-(Bis(3,4-Dimethylphenoxy)Phosphoryl)Propylcarbamate 在 氢溴酸 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Human Neutrophil Elastase Phosphonic Inhibitors with Improved Potency of Action

  摘要：

  Herein, we present the synthesis and the measurement of the inhibitory activity of novel peptidyl derivatives of alpha-aminoalkylphosphonate diaryl esters as human neutrophil elastase inhibitors. Their selectivity against other serine proteases, including porcine pancreatic elastase, chymotrypsin, and trypsin, was also demonstrated. We also describe the preparation of single peptide diastereomers. The most active and selective compound developed possessed a k(inact)/K-1 of 2353000 M-1 s(-1), which is the most potent irreversible peptidyl inhibitor of human neutrophil elastase reported to date. The peptidyl inhibitors were demonstrated to be stable in PBS buffer and human plasma, as were their complexes with HNE.

  DOI：

  10.1021/jm300599x
• 作为产物：
  描述：

  氨基甲酸苄酯 、 tris(3,4-dimethylphenyl)phosphite 、 丙醛 在 溶剂黄146 作用下， 反应 2.0h， 生成 Benzyl 1-(Bis(3,4-Dimethylphenoxy)Phosphoryl)Propylcarbamate
  参考文献：
  名称：

  α-氨基芳烷基膦酸的新型芳香单酯作为氨基肽酶N / CD13的抑制剂

  摘要：

  通过选择性水解相应的α-氨基芳烷基膦酸芳族二酯，合成了一系列新的α-氨基芳烷基膦酸芳族单酯。开发了新的潜在的氨基肽酶N / CD13抑制剂，这是一种在肿瘤血管生成中很重要的酶。高苯丙氨酸和正亮氨酸相关的单芳基膦酸酯的一些衍生物显示出比相应的α-氨基芳烷基膦酸对氨基肽酶N / CD13更高的抑制能力。单独或与TNF-α一起检测了一种新抑制剂对人PANC-1和HT-1080细胞系生长的影响。

  DOI：

  10.1016/j.bmc.2010.02.056

文献信息

• New aromatic monoesters of α-aminoaralkylphosphonic acids as inhibitors of aminopeptidase N/CD13
  作者：Renata Grzywa、Anna M. Sokol、Marcin Sieńczyk、Magdalena Radziszewicz、Beata Kościołek、Michael P. Carty、Józef Oleksyszyn

  DOI：10.1016/j.bmc.2010.02.056

  日期：2010.4

  A series of new aromatic monoesters of α-aminoaralkylphosphonic acids were synthesized by selective hydrolysis of corresponding aromatic diesters of α-aminoaralkylphosphonic acids. New potential inhibitors of aminopeptidase N/CD13, an enzyme important in tumour angiogenesis, were developed. Some derivatives of the homophenylalanine and norleucine related monoaryl phosphonates displayed higher inhibition

  通过选择性水解相应的α-氨基芳烷基膦酸芳族二酯，合成了一系列新的α-氨基芳烷基膦酸芳族单酯。开发了新的潜在的氨基肽酶N / CD13抑制剂，这是一种在肿瘤血管生成中很重要的酶。高苯丙氨酸和正亮氨酸相关的单芳基膦酸酯的一些衍生物显示出比相应的α-氨基芳烷基膦酸对氨基肽酶N / CD13更高的抑制能力。单独或与TNF-α一起检测了一种新抑制剂对人PANC-1和HT-1080细胞系生长的影响。
• Human Neutrophil Elastase Phosphonic Inhibitors with Improved Potency of Action
  作者：Łukasz Winiarski、Józef Oleksyszyn、Marcin Sieńczyk

  DOI：10.1021/jm300599x

  日期：2012.7.26

  Herein, we present the synthesis and the measurement of the inhibitory activity of novel peptidyl derivatives of alpha-aminoalkylphosphonate diaryl esters as human neutrophil elastase inhibitors. Their selectivity against other serine proteases, including porcine pancreatic elastase, chymotrypsin, and trypsin, was also demonstrated. We also describe the preparation of single peptide diastereomers. The most active and selective compound developed possessed a k(inact)/K-1 of 2353000 M-1 s(-1), which is the most potent irreversible peptidyl inhibitor of human neutrophil elastase reported to date. The peptidyl inhibitors were demonstrated to be stable in PBS buffer and human plasma, as were their complexes with HNE.