4-(2-Heptadecynyloxymethyl)phenylmethanol | 152124-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-Heptadecynyloxymethyl)phenylmethanol
• 英文别名: [4-(Heptadec-2-ynoxymethyl)phenyl]methanol
• CAS: 152124-19-1
• 化学式: C₂₅H₄₀O₂
• 分子量: 372.591
• InChiKey: ZFYMNXDUYMIEKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  506.0±35.0 °C(predicted)
• 密度：
  0.955±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-Heptadecynyloxymethyl)phenylmethanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 1.0h， 以93%的产率得到1-Iodomethyl-4-(2-heptadecynyloxymethyl) benzene
  参考文献：
  名称：

  (Carboxyalkyl)benzyl Propargyl Ethers as Selective Inhibitors of Leukocyte-Type 12-Lipoxygenases

  摘要：

  A series of (carboxyalkyl)benzyl propargyl ethers was synthesized and tested as inhibitors of 12-lipoxygenase (12-LO) from porcine leukocyte cytosol. Optimum activity was displayed by 3-[4-[(2-tridecynyloxy)methyl]phenyl]propanoic acid. Altering the length of the alkyl side chain attached to the acetylenic group reduced activity. Changing the substitution pattern in the (carboxyalkyl)benzyl group from para to meta or ortho also reduced activity. Analogs in which the triple bond was replaced by a double bond or an allene displayed reduced activity, whereas fully saturated analogs were inactive. High concentrations (10 mu M) of the most potent acetylenic (carboxylalkyl)benzyl ethers did not inhibit human platelet 12-LO, human neutrophil 5-LO, rabbit reticulocyte 15-LO, or soybean 15-LO. Thus, this class of compounds represents the first example of isoform specific LO inhibitors.

  DOI：

  10.1021/jm9606047
• 作为产物：
  描述：

  对苯二甲醇 在 咪唑 、 氢氟酸 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 26.75h， 生成 4-(2-Heptadecynyloxymethyl)phenylmethanol
  参考文献：
  名称：

  (Carboxyalkyl)benzyl Propargyl Ethers as Selective Inhibitors of Leukocyte-Type 12-Lipoxygenases

  摘要：

  A series of (carboxyalkyl)benzyl propargyl ethers was synthesized and tested as inhibitors of 12-lipoxygenase (12-LO) from porcine leukocyte cytosol. Optimum activity was displayed by 3-[4-[(2-tridecynyloxy)methyl]phenyl]propanoic acid. Altering the length of the alkyl side chain attached to the acetylenic group reduced activity. Changing the substitution pattern in the (carboxyalkyl)benzyl group from para to meta or ortho also reduced activity. Analogs in which the triple bond was replaced by a double bond or an allene displayed reduced activity, whereas fully saturated analogs were inactive. High concentrations (10 mu M) of the most potent acetylenic (carboxylalkyl)benzyl ethers did not inhibit human platelet 12-LO, human neutrophil 5-LO, rabbit reticulocyte 15-LO, or soybean 15-LO. Thus, this class of compounds represents the first example of isoform specific LO inhibitors.

  DOI：

  10.1021/jm9606047

文献信息

• US5238832A
  申请人：——

  公开号：US5238832A

  公开（公告）日：1993-08-24
• (Carboxyalkyl)benzyl Propargyl Ethers as Selective Inhibitors of Leukocyte-Type 12-Lipoxygenases
  作者：Gilles Gorins、Lethea Kuhnert、Carl R. Johnson、Lawrence J. Marnett

  DOI：10.1021/jm9606047

  日期：1996.1.1

  A series of (carboxyalkyl)benzyl propargyl ethers was synthesized and tested as inhibitors of 12-lipoxygenase (12-LO) from porcine leukocyte cytosol. Optimum activity was displayed by 3-[4-[(2-tridecynyloxy)methyl]phenyl]propanoic acid. Altering the length of the alkyl side chain attached to the acetylenic group reduced activity. Changing the substitution pattern in the (carboxyalkyl)benzyl group from para to meta or ortho also reduced activity. Analogs in which the triple bond was replaced by a double bond or an allene displayed reduced activity, whereas fully saturated analogs were inactive. High concentrations (10 mu M) of the most potent acetylenic (carboxylalkyl)benzyl ethers did not inhibit human platelet 12-LO, human neutrophil 5-LO, rabbit reticulocyte 15-LO, or soybean 15-LO. Thus, this class of compounds represents the first example of isoform specific LO inhibitors.