O,O-bis(2-cyanoethyl) O-2-(hexadecyloxy)-3-methoxypropyl phosphorothioate | 1426539-39-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 英文名称: O,O-bis(2-cyanoethyl) O-2-(hexadecyloxy)-3-methoxypropyl phosphorothioate
• 英文别名: 3-[2-Cyanoethoxy-(2-hexadecoxy-3-methoxypropoxy)phosphinothioyl]oxypropanenitrile；3-[2-cyanoethoxy-(2-hexadecoxy-3-methoxypropoxy)phosphinothioyl]oxypropanenitrile
• CAS: 1426539-39-0
• 化学式: C₂₆H₄₉N₂O₅PS
• 分子量: 532.725
• InChiKey: OYVZYERFMKOPAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  35
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O,O-bis(2-cyanoethyl) O-2-(hexadecyloxy)-3-methoxypropyl phosphorothioate 在 N,O-双三甲硅基乙酰胺 、 叔丁胺 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 生成 Sodium;(2-hexadecoxy-3-methoxypropoxy)-hydroxy-oxido-sulfanylidene-lambda5-phosphane
  参考文献：
  名称：

  Phosphorothioate analogs of sn-2 radyl lysophosphatidic acid (LPA): Metabolically stabilized LPA receptor agonists

  摘要：

  We describe an efficient synthesis of metabolically stabilized sn-2 radyl phosphorothioate analogs of lysophosphatidic acid (LPA), and the determination of the agonist activity of each analog for the six LPA receptors (LPA(1-6)) using a recently developed TGF alpha shedding assay. In general, the sn-2 radyl OMPT analogs showed similar agonist activities to the previous 1-oleoyl-2-O-methyl-glycerophosphothioate (sn-1 OMPT) analogs for LPA(1-6) receptors. In most cases, the sn-2 radyl-OMPT analogs were more potent agonists than LPA itself. Most importantly, sn-2 alkyl OMPT analogs were very potent LPA(5) and LPA(6) agonists. The availability of sn-2 radyl OPMT analogs further refines the structure-activity relationships for ligand-receptor interactions for this class of GPCRs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.002
• 作为产物：
  描述：

  ((2-(十六烷氧基)-3-甲氧基丙氧基)甲三基)三苯 在 吡啶 、 四氮唑 、 二硫化碳 、 sulfur 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 O,O-bis(2-cyanoethyl) O-2-(hexadecyloxy)-3-methoxypropyl phosphorothioate
  参考文献：
  名称：

  Phosphorothioate analogs of sn-2 radyl lysophosphatidic acid (LPA): Metabolically stabilized LPA receptor agonists

  摘要：

  We describe an efficient synthesis of metabolically stabilized sn-2 radyl phosphorothioate analogs of lysophosphatidic acid (LPA), and the determination of the agonist activity of each analog for the six LPA receptors (LPA(1-6)) using a recently developed TGF alpha shedding assay. In general, the sn-2 radyl OMPT analogs showed similar agonist activities to the previous 1-oleoyl-2-O-methyl-glycerophosphothioate (sn-1 OMPT) analogs for LPA(1-6) receptors. In most cases, the sn-2 radyl-OMPT analogs were more potent agonists than LPA itself. Most importantly, sn-2 alkyl OMPT analogs were very potent LPA(5) and LPA(6) agonists. The availability of sn-2 radyl OPMT analogs further refines the structure-activity relationships for ligand-receptor interactions for this class of GPCRs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.002

文献信息

• Phosphorothioate analogs of sn-2 radyl lysophosphatidic acid (LPA): Metabolically stabilized LPA receptor agonists
  作者：Guowei Jiang、Asuka Inoue、Junken Aoki、Glenn D. Prestwich

  DOI：10.1016/j.bmcl.2013.01.002

  日期：2013.3

  We describe an efficient synthesis of metabolically stabilized sn-2 radyl phosphorothioate analogs of lysophosphatidic acid (LPA), and the determination of the agonist activity of each analog for the six LPA receptors (LPA(1-6)) using a recently developed TGF alpha shedding assay. In general, the sn-2 radyl OMPT analogs showed similar agonist activities to the previous 1-oleoyl-2-O-methyl-glycerophosphothioate (sn-1 OMPT) analogs for LPA(1-6) receptors. In most cases, the sn-2 radyl-OMPT analogs were more potent agonists than LPA itself. Most importantly, sn-2 alkyl OMPT analogs were very potent LPA(5) and LPA(6) agonists. The availability of sn-2 radyl OPMT analogs further refines the structure-activity relationships for ligand-receptor interactions for this class of GPCRs. (C) 2013 Elsevier Ltd. All rights reserved.