naphthalen-1-yl(octyloxy)methylphosphonic acid | 1123189-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-1-yl(octyloxy)methylphosphonic acid
• 英文别名: (+/-)-Naphthalen-1-yl(octyloxy)methylphosphonic acid；[naphthalen-1-yl(octoxy)methyl]phosphonic acid
• CAS: 1123189-27-4
• 化学式: C₁₉H₂₇O₄P
• 分子量: 350.395
• InChiKey: RNQQAOXGNBOQNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl naphthalen-1-yl(octyloxy)methylphosphonate 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以100%的产率得到naphthalen-1-yl(octyloxy)methylphosphonic acid
  参考文献：
  名称：

  Inhibition of purple acid phosphatase with α-alkoxynaphthylmethylphosphonic acids

  摘要：

  Purple acid phosphatases (PAPs) are binuclear hydrolases that catalyse the hydrolysis of a range of phosphorylated substrates. Human PAP is a major histochemical marker for the diagnosis of osteoporosis. In patients suffering from this disorder, PAP activity contributes to increased bone resorption and, therefore, human PAP is a key target for the development of anti-osteoporotic drugs. This manuscript describes the design and synthesis of derivatives of 1-naphthylmethylphosphonic acids as inhibitors of PAP. The K(i) values of these compounds are as low as 4 mu M, the lowest reported to date for a PAP inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.125

文献信息

• Inhibition of purple acid phosphatase with α-alkoxynaphthylmethylphosphonic acids
  作者：Ross P. McGeary、Peter Vella、Jeffrey Y.W. Mak、Luke W. Guddat、Gerhard Schenk

  DOI：10.1016/j.bmcl.2008.10.125

  日期：2009.1

  Purple acid phosphatases (PAPs) are binuclear hydrolases that catalyse the hydrolysis of a range of phosphorylated substrates. Human PAP is a major histochemical marker for the diagnosis of osteoporosis. In patients suffering from this disorder, PAP activity contributes to increased bone resorption and, therefore, human PAP is a key target for the development of anti-osteoporotic drugs. This manuscript describes the design and synthesis of derivatives of 1-naphthylmethylphosphonic acids as inhibitors of PAP. The K(i) values of these compounds are as low as 4 mu M, the lowest reported to date for a PAP inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.