(4-phenylbutyl)phosphonic acid benzyl ester | 106019-30-1

• 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: (4-phenylbutyl)phosphonic acid benzyl ester
• 英文别名: benzyl 4-phenylbutylphosphonic acid；(4-phenylbutyl)phosphonic acid, dibenzyl ester；4-Phenylbutylphosphonic acid-mono-benzyl ester；4-phenylbutyl(phenylmethoxy)phosphinic acid
• CAS: 106019-30-1
• 化学式: C₁₇H₂₁O₃P
• 分子量: 304.326
• InChiKey: BAVYPQIIBFZYGH-UHFFFAOYSA-N

物化性质

• 沸点：
  470.4±48.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-phenylbutyl)phosphonic acid benzyl ester 在 palladium on activated charcoal 草酰氯 、 氢气 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 N-[hydroxy(4-phenylbutyl)phosphinyl]-L-glutamic acid tripotassium salt
  参考文献：
  名称：

  Probing for a hydrophobic a binding register in prostate-specific membrane antigen with phenylalkylphosphonamidates

  摘要：

  To explore for the existence of an auxiliary hydrophobic binding register remote from the active site of PSMA a series of phenylalkylphosphonamidate derivatives of glutamic acid were synthesized and evaluated for their inhibitory potencies against PSMA. Both the phenyl- and benzylphosphonamidates (1a and 1b) exhibited only modest inhibitory potency against. The phenethyl analog 1c was intermediate in inhibitory potency while inhibitors possessing a longer alkyl tether from the phenyl ring, resulted in markedly improved K-i values. The greatest inhibitory potency was obtained for the inhibitors in which the phenyl ring was extended furthest from the central phosphorus (if, n = 5 and I g, n = 6). The slightly serrated pattern that emerged as the alkyl tether increased from three to six methylene units suggests that inhibitory potency is not simply correlated to increased hydrophobicity imparted by the phenylalkyl chain, but rather that one or more hydrophobic binding registers may exist remote from the substrate recognition architecture in the active site of PSMA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.031
• 作为产物：
  描述：

  L-脯氨酸苄酯盐酸盐 在 二苯基膦叠氮化物 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 (4-phenylbutyl)phosphonic acid benzyl ester
  参考文献：
  名称：

  由亚膦酸合成膦酸单酯

  摘要：

  通过DCC-DMAP介导的亚膦酸酯化和氧化生成的单膦酸酯，以两步法制备膦酸酯单酯。

  DOI：

  10.1016/s0040-4039(00)84364-6

文献信息

• Orally active phosphonyl hydroxyacyl prolines
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04745196A1

  公开（公告）日：1988-05-17

  This invention is directed to orally active antihypertensive agents of the formula ##STR1## wherein R.sub.1 is certain alkyl or aralkyl groups.

  这项发明涉及口服活性降压药物，其化学式为##STR1## 其中R.sub.1是特定的烷基或芳基烷基基团。
• Process for preparing phosphonic acids
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04670193A1

  公开（公告）日：1987-06-02

  A process for preparing phosphonic acids of the structure ##STR1## wherein R.sub.1 is lower alkyl, aryl, cycloalkyl or arylalkyl, and R.sub.2 is H, benzyl or ##STR2## by oxidizing the corresponding phosphonous acid ##STR3## employing as the oxidizing agent potassium permanganate or sodium periodate.

  一种制备具有结构 ##STR1## 的膦酸的过程，其中R.sub.1为低碳基，芳基，环烷基或芳基烷基，而R.sub.2为H，苯甲基或##STR2##，通过使用高锰酸钾或过碘酸钠作为氧化剂氧化相应的膦酸。
• Dual Angiotensin Converting Enzyme/Thromboxane Synthase Inhibitors
  作者：Gary M. Ksander、Mark Erion、Andrew M. Yuan、Clive G. Diefenbacher、Lena El-Chehabi、Don Cote、Nigel Levens

  DOI：10.1021/jm00038a011

  日期：1994.6

  A variety of compounds were prepared to determine whether dual angiotensin converting enzyme (ACE)/thromboxane synthase (TxS) inhibition could be obtained in the same molecule. These compounds would be used to explore the concept that a dual inhibitor would have superior antihypertensive activity in the spontaneous hypertensive rat compared to an ACE inhibitor. Potent in vitro dual ACE and TxS inhibition was obtained in the same molecule with five series of compounds. Potent blood pressure lowering in the SHR was observed after oral administration of 8b and 11. However, a correlation between blood pressure lowering and the Al presser response inhibition was not observed. The blood pressure-lowering actions of enalapril were significantly potentiated by concurrent administration of 3, a thromboxane synthase inhibitor. Analysis of the area under the curve for 24 h showed nearly a doubling of the blood pressure-lowering effect.
• US4670193A
  申请人：——

  公开号：US4670193A

  公开（公告）日：1987-06-02
• Probing for a hydrophobic a binding register in prostate-specific membrane antigen with phenylalkylphosphonamidates
  作者：Jack Maung、Jeremy P. Mallari、Teri A. Girtsman、Lisa Y. Wu、Jennifer A. Rowley、Nicholas M. Santiago、Alan N. Brunelle、Clifford E. Berkman

  DOI：10.1016/j.bmc.2004.06.031

  日期：2004.9

  To explore for the existence of an auxiliary hydrophobic binding register remote from the active site of PSMA a series of phenylalkylphosphonamidate derivatives of glutamic acid were synthesized and evaluated for their inhibitory potencies against PSMA. Both the phenyl- and benzylphosphonamidates (1a and 1b) exhibited only modest inhibitory potency against. The phenethyl analog 1c was intermediate in inhibitory potency while inhibitors possessing a longer alkyl tether from the phenyl ring, resulted in markedly improved K-i values. The greatest inhibitory potency was obtained for the inhibitors in which the phenyl ring was extended furthest from the central phosphorus (if, n = 5 and I g, n = 6). The slightly serrated pattern that emerged as the alkyl tether increased from three to six methylene units suggests that inhibitory potency is not simply correlated to increased hydrophobicity imparted by the phenylalkyl chain, but rather that one or more hydrophobic binding registers may exist remote from the substrate recognition architecture in the active site of PSMA. (C) 2004 Elsevier Ltd. All rights reserved.