(2S)-2-(((4-phenylbutyl)hydroxyphosphoryl)oxy)hexanoic acid | 152830-19-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-2-(((4-phenylbutyl)hydroxyphosphoryl)oxy)hexanoic acid
• 英文别名: (2S)-2-{[(4-phenylbutyl)hydroxyphosphoryl]oxy}hexanoic acid；(2S)-2-[hydroxy(4-phenylbutyl)phosphoryl]oxyhexanoic acid
• CAS: 152830-19-8
• 化学式: C₁₆H₂₅O₅P
• 分子量: 328.345
• InChiKey: VBGUBCOOWMHUQU-HNNXBMFYSA-N

物化性质

• 沸点：
  504.9±60.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-(((4-phenylbutyl)hydroxyphosphoryl)oxy)hexanoic acid 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (5S)-5-butyl-2-oxo-2-(4-phenylbutyl)-1,3,2lambda5-dioxaphospholan-4-one
  参考文献：
  名称：

  Non-peptide Renin Inhibitors Containing 2-(((3-Phenylpropyl)phosphoryl)oxy)alkanoic Acid Moieties as P2-P3 Replacements

  摘要：

  A series of novel renin inhibitors containing 2-(((3-phenylpropyl)phosphoryl)oxy) alkanoic acid moieties as P-2-P-3 surrogates are presented. The P-2-P-3 mimetics were obtained from (omega-phenylalkyl)phosphinic acids la-c and 2-hydroxyalkanoic acid benzyl esters 2a-f by N,N'-dicyclohexylcarbodiimide-mediated coupling and subsequent oxidation with sodium metaperjodate. Ester cleavage of these derivatives and coupling with P-1-P-1' transition-state mimetics I-VII provided highly selective compounds with inhibitory potencies in the lower nanomolar range. Small renin inhibitors, such as analogues 8c and 8h with molecular weights of 539 and 537, respectively, could be prepared. These compounds exhibited IC50 values of about 20 nM against human plasma renin. Compound 7i was examined in vivo for its hypotensive effect. In salt-depleted cynomolgus monkeys, 7i inhibited plasma renin activity almost completely and lowered blood pressure after oral administration of a dose of 30 mg/kg.

  DOI：

  10.1021/jm00030a008
• 作为产物：
  描述：

  (S)-2-羟基己酸 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium periodate 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (2S)-2-(((4-phenylbutyl)hydroxyphosphoryl)oxy)hexanoic acid
  参考文献：
  名称：

  Non-peptide Renin Inhibitors Containing 2-(((3-Phenylpropyl)phosphoryl)oxy)alkanoic Acid Moieties as P2-P3 Replacements

  摘要：

  A series of novel renin inhibitors containing 2-(((3-phenylpropyl)phosphoryl)oxy) alkanoic acid moieties as P-2-P-3 surrogates are presented. The P-2-P-3 mimetics were obtained from (omega-phenylalkyl)phosphinic acids la-c and 2-hydroxyalkanoic acid benzyl esters 2a-f by N,N'-dicyclohexylcarbodiimide-mediated coupling and subsequent oxidation with sodium metaperjodate. Ester cleavage of these derivatives and coupling with P-1-P-1' transition-state mimetics I-VII provided highly selective compounds with inhibitory potencies in the lower nanomolar range. Small renin inhibitors, such as analogues 8c and 8h with molecular weights of 539 and 537, respectively, could be prepared. These compounds exhibited IC50 values of about 20 nM against human plasma renin. Compound 7i was examined in vivo for its hypotensive effect. In salt-depleted cynomolgus monkeys, 7i inhibited plasma renin activity almost completely and lowered blood pressure after oral administration of a dose of 30 mg/kg.

  DOI：

  10.1021/jm00030a008

文献信息

• Raddatz Peter, Minck Klaus-Otto, Rippmann Friedrich, Schmitges Claus-Joch+, J. Med. Chem, 37 (1994) N 4, S 486-497
  作者：Raddatz Peter, Minck Klaus-Otto, Rippmann Friedrich, Schmitges Claus-Joch+

  DOI：——

  日期：——
• Non-peptide Renin Inhibitors Containing 2-(((3-Phenylpropyl)phosphoryl)oxy)alkanoic Acid Moieties as P2-P3 Replacements
  作者：Peter Raddatz、Klaus-Otto Minck、Friedrich Rippmann、Claus-Jochen Schmitges

  DOI：10.1021/jm00030a008

  日期：1994.2

  A series of novel renin inhibitors containing 2-(((3-phenylpropyl)phosphoryl)oxy) alkanoic acid moieties as P-2-P-3 surrogates are presented. The P-2-P-3 mimetics were obtained from (omega-phenylalkyl)phosphinic acids la-c and 2-hydroxyalkanoic acid benzyl esters 2a-f by N,N'-dicyclohexylcarbodiimide-mediated coupling and subsequent oxidation with sodium metaperjodate. Ester cleavage of these derivatives and coupling with P-1-P-1' transition-state mimetics I-VII provided highly selective compounds with inhibitory potencies in the lower nanomolar range. Small renin inhibitors, such as analogues 8c and 8h with molecular weights of 539 and 537, respectively, could be prepared. These compounds exhibited IC50 values of about 20 nM against human plasma renin. Compound 7i was examined in vivo for its hypotensive effect. In salt-depleted cynomolgus monkeys, 7i inhibited plasma renin activity almost completely and lowered blood pressure after oral administration of a dose of 30 mg/kg.