3-[4-(2-Pentadecynyloxymethyl)phenyl]propanoic Acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-[4-(2-Pentadecynyloxymethyl)phenyl]propanoic Acid
• 英文别名: 3-(4-Pentadec-2-ynyloxymethyl-phenyl)-propionic acid；3-[4-(pentadec-2-ynoxymethyl)phenyl]propanoic acid
• 化学式: C₂₅H₃₈O₃
• 分子量: 386.575
• InChiKey: BUUHYIKUIFHMAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对苯二甲醇 在 咪唑 、 氢氟酸 、 碘 、 sodium hydride 、 三苯基膦 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 41.25h， 生成 3-[4-(2-Pentadecynyloxymethyl)phenyl]propanoic Acid
  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
• [EN] ARYL ALIPHATIC ACIDS<br/>[FR] ACIDES ALIPHATIQUES D'ARYLE
  申请人：BOARD OF GOVERNORS OF WAYNE STATE UNIVERSITY

  公开号：WO1993025521A1

  公开（公告）日：1993-12-23

  (EN) Novel aryl aliphatic acids or derivatives thereof of the general formula: R-(Cx-Cy)-(CmH2m)-G-C(R1)2-Ar-(CnH2n)-COOR2 are described which exhibit inhibiting activity against 12-lipoxygenase. The compounds are characterized by having a low level of toxicity. Also included are salts and esters of the aliphatic acids.(FR) L'invention se rapporte à de nouveaux acides aliphatiques d'aryle, ou à des dérivés de ceux-ci, répondant à la formule générale: R-(Cx-Cy)-(CmH2m)-G-C(R1)2-Ar-(CnH2n)-COOR2 et agissant comme inhibiteurs de 12-lipoxygénase. Ces composés sont caractérisés par un faible niveau de toxicité. Des sels et esters de ces acides aliphatiques sont également décrits.
• (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.