[(R)-3-tert-Butoxycarbonylamino-3-(4-decyl-phenylcarbamoyl)-propyl]-phosphonic acid diethyl ester | 925706-74-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(R)-3-tert-Butoxycarbonylamino-3-(4-decyl-phenylcarbamoyl)-propyl]-phosphonic acid diethyl ester
• CAS: 925706-74-7
• 化学式: C₂₉H₅₁N₂O₆P
• 分子量: 554.707
• InChiKey: QQVNTSMYPMKUNA-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.86
• 重原子数：
  38.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(R)-3-tert-Butoxycarbonylamino-3-(4-decyl-phenylcarbamoyl)-propyl]-phosphonic acid diethyl ester 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以31 mg的产率得到[(R)-3-Amino-3-(4-decyl-phenylcarbamoyl)-propyl]-phosphonic acid; hydrobromide
  参考文献：
  名称：

  Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists

  摘要：

  The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine I-phosphate (SIP) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described. In vitro binding assays showed that the implementation of phosphonates as phosphate mimetics provided compounds with similar receptor binding affinities as compared to their phosphate precursors. meta-substituted arylamide phosphonates were discovered to be antagonists of the S1P(1) and S1P(3) receptors. When administered to mice, an antagonist blocked the lymphopenia evoked by a SIP receptor agonist and caused capillary leakage in both lung and kidney. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.060
• 作为产物：
  描述：

  (S)-(-)-3-BOC-4-甲氧羰基-2,2-二甲基-1,3-恶唑烷 在 palladium on activated charcoal sodium tetrahydroborate 、 正丁基锂 、 jones reagent 、 草酰氯 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 40.25h， 生成 [(R)-3-tert-Butoxycarbonylamino-3-(4-decyl-phenylcarbamoyl)-propyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists

  摘要：

  The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine I-phosphate (SIP) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described. In vitro binding assays showed that the implementation of phosphonates as phosphate mimetics provided compounds with similar receptor binding affinities as compared to their phosphate precursors. meta-substituted arylamide phosphonates were discovered to be antagonists of the S1P(1) and S1P(3) receptors. When administered to mice, an antagonist blocked the lymphopenia evoked by a SIP receptor agonist and caused capillary leakage in both lung and kidney. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.060