1-(4-benzyloxyphenyl)-1-hexadecanol | 194658-61-2

• 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: 1-(4-benzyloxyphenyl)-1-hexadecanol
• CAS: 194658-61-2
• 化学式: C₂₉H₄₄O₂
• 分子量: 424.667
• InChiKey: VERCKZDRPUJNND-UHFFFAOYSA-N

物化性质

• 沸点：
  548.3±38.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.78
• 重原子数：
  31.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-benzyloxyphenyl)-1-hexadecanol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氨基磺酰氯 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (4-Hexadecylphenyl) sulfamate
  参考文献：
  名称：

  Structure-activity relationship studies of the amide functionality in (p-O-sulfamoyl)-N-alkanoyl tyramines as estrone sulfatase inhibitors

  摘要：

  Recently, we reported the synthesis and biochemical studies of a series of (p-O-sulfamoyl)-N-alkanoyl tyramines as nonsteroidal estrone sulfatase inhibitors. One of the most potent inhibitors in this series is (p-O-sulfamoyl)-N-tridecanoyl tyramine 1 with an IC50 value of 61.3 nM. In this study, we synthesized four analogs of 1 (compounds 2-5) to investigate the structure-activity relationships of the amide functionality in (p-O-sulfamoyl)-N-tridecanoyl tyramine. Replacement of the amide functionality in 1 with an ethylene moiety to form the alkyl analog 5 resulted in complete loss of sulfatase inhibitory activity (IC50 of 61.3 nM vs. >20 mu M). The keto, hydroxy, and ester analogs (inhibitors 2-4) are 8-15 times less in affinity to the sulfatase than inhibitor 1. However, their inhibitory activities are significantly higher than the alkyl analog 5. The results suggest that the amide functionality is favorable for sulfatase inhibitory activity and that there may be a hydrogen bonding component to the enzyme interaction in this region. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00038-x
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 Pentadecylmagnesium Bromide 以 四氢呋喃 为溶剂， 反应 3.0h， 以86.5%的产率得到1-(4-benzyloxyphenyl)-1-hexadecanol
  参考文献：
  名称：

  Structure-activity relationship studies of the amide functionality in (p-O-sulfamoyl)-N-alkanoyl tyramines as estrone sulfatase inhibitors

  摘要：

  Recently, we reported the synthesis and biochemical studies of a series of (p-O-sulfamoyl)-N-alkanoyl tyramines as nonsteroidal estrone sulfatase inhibitors. One of the most potent inhibitors in this series is (p-O-sulfamoyl)-N-tridecanoyl tyramine 1 with an IC50 value of 61.3 nM. In this study, we synthesized four analogs of 1 (compounds 2-5) to investigate the structure-activity relationships of the amide functionality in (p-O-sulfamoyl)-N-tridecanoyl tyramine. Replacement of the amide functionality in 1 with an ethylene moiety to form the alkyl analog 5 resulted in complete loss of sulfatase inhibitory activity (IC50 of 61.3 nM vs. >20 mu M). The keto, hydroxy, and ester analogs (inhibitors 2-4) are 8-15 times less in affinity to the sulfatase than inhibitor 1. However, their inhibitory activities are significantly higher than the alkyl analog 5. The results suggest that the amide functionality is favorable for sulfatase inhibitory activity and that there may be a hydrogen bonding component to the enzyme interaction in this region. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00038-x