(3-Hexadecoxy-2-hydroxypropyl) 6-(trimethylazaniumyl)hexyl phosphate | 99884-92-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: (3-Hexadecoxy-2-hydroxypropyl) 6-(trimethylazaniumyl)hexyl phosphate
• CAS: 99884-92-1
• 化学式: C₂₈H₆₀NO₆P
• 分子量: 537.761
• InChiKey: DHSISCAMTZDQIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3-Hexadecoxy-2-hydroxypropyl) 6-(trimethylazaniumyl)hexyl phosphate 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 1-O-Hexadecyl-2-acetyl-sn-glycero-3-phospho-(N,N,N-trimethyl)-hexanolamine
  参考文献：
  名称：

  Analogs of platelet activating factor. 4. Some modifications of the phosphocholine moiety

  摘要：

  Racemic analogues of platelet activating factor (PAF) in which the methylene bridge separating the phosphate and trimethylammonium moieties is altered in length (7a-f) have been prepared. Increasing the length of this bridge results in a progressive decrease in the hypotensive and platelet aggregation responses. Analogues in which the phosphocholine group is substituted with a methyl group (7h and 7i) or a phenyl group (5j) or in which the methylene bridge is replaced with a meta-substituted benzyl group (5k) have been prepared. With respect to both the blood pressure and platelet aggregation responses, 7i and 5k showed little if any changes in potency compared to racemic C16-PAF (1a). While 7h is more potent than 1a with respect to both the hypotensive and platelet aggregation properties, 5j is less potent. Replacement of the phosphate moiety of C18-PAF (1b) with a phosphonate group (7g) leads to decreased activity in both assays. Analogue 11, in which the phosphocholine group has been replaced with a 4-(trimethylammonio)butoxy group, exhibited no detectable hypotensive or platelet aggregating activity. None of the analogues exhibited a separation of the blood pressure and platelet aggregation activities.

  DOI：

  10.1021/jm00153a005
• 作为产物：
  描述：

  2-benzyloxy-3-hexadecyloxy-1-propanol 在 palladium on activated charcoal 氢气 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 氯仿 、 乙腈 为溶剂， 25.0 ℃ 、172.37 kPa 条件下， 反应 41.5h， 生成 (3-Hexadecoxy-2-hydroxypropyl) 6-(trimethylazaniumyl)hexyl phosphate
  参考文献：
  名称：

  Analogs of platelet activating factor. 4. Some modifications of the phosphocholine moiety

  摘要：

  Racemic analogues of platelet activating factor (PAF) in which the methylene bridge separating the phosphate and trimethylammonium moieties is altered in length (7a-f) have been prepared. Increasing the length of this bridge results in a progressive decrease in the hypotensive and platelet aggregation responses. Analogues in which the phosphocholine group is substituted with a methyl group (7h and 7i) or a phenyl group (5j) or in which the methylene bridge is replaced with a meta-substituted benzyl group (5k) have been prepared. With respect to both the blood pressure and platelet aggregation responses, 7i and 5k showed little if any changes in potency compared to racemic C16-PAF (1a). While 7h is more potent than 1a with respect to both the hypotensive and platelet aggregation properties, 5j is less potent. Replacement of the phosphate moiety of C18-PAF (1b) with a phosphonate group (7g) leads to decreased activity in both assays. Analogue 11, in which the phosphocholine group has been replaced with a 4-(trimethylammonio)butoxy group, exhibited no detectable hypotensive or platelet aggregating activity. None of the analogues exhibited a separation of the blood pressure and platelet aggregation activities.

  DOI：

  10.1021/jm00153a005

文献信息

• Analogs of platelet activating factor. 4. Some modifications of the phosphocholine moiety
  作者：A. Wissner、R. E. Schaub、P. E. Sum、C. A. Kohler、B. M. Goldstein

  DOI：10.1021/jm00153a005

  日期：1986.3

  Racemic analogues of platelet activating factor (PAF) in which the methylene bridge separating the phosphate and trimethylammonium moieties is altered in length (7a-f) have been prepared. Increasing the length of this bridge results in a progressive decrease in the hypotensive and platelet aggregation responses. Analogues in which the phosphocholine group is substituted with a methyl group (7h and 7i) or a phenyl group (5j) or in which the methylene bridge is replaced with a meta-substituted benzyl group (5k) have been prepared. With respect to both the blood pressure and platelet aggregation responses, 7i and 5k showed little if any changes in potency compared to racemic C16-PAF (1a). While 7h is more potent than 1a with respect to both the hypotensive and platelet aggregation properties, 5j is less potent. Replacement of the phosphate moiety of C18-PAF (1b) with a phosphonate group (7g) leads to decreased activity in both assays. Analogue 11, in which the phosphocholine group has been replaced with a 4-(trimethylammonio)butoxy group, exhibited no detectable hypotensive or platelet aggregating activity. None of the analogues exhibited a separation of the blood pressure and platelet aggregation activities.