6-(3-乙酰基-4-羟基-2-丙基-苯氧基)-己酸 | 106627-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-(3-乙酰基-4-羟基-2-丙基-苯氧基)-己酸
• 英文名称: 6-(3-Acetyl-4-hydroxy-2-propylphenoxy)hexanoic acid
• CAS: 106627-19-4
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: AIJCKOKEEJBPLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 镍 三乙基硅烷 、 甲酸 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 乙酸乙酯 、 丙酮 、 丁酮 为溶剂， 25.0~220.0 ℃ 、413.69 kPa 条件下， 反应 174.5h， 生成 6-(3-乙酰基-4-羟基-2-丙基-苯氧基)-己酸
  参考文献：
  名称：

  Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives

  摘要：

  A series of derivatives of 2,4-dihydroxy-3-propylacetophenone(1) were prepared and examined for their ability to block leukotriene D4 (LTD4) induced contraction of guinea pig ileum. Straight-chain carboxylic acids where the carboxyl group was separated from the acetophenone moiety by varying numbers of methylenes were evaluated, and maximum activity was obtained with the pentamethylene acid (6). Examination of ring substitution showed that the 2-propyl-3-hydroxy-4-acetyl substitution pattern was required for maximum LTD4 antagonist activity. Additional chain terminal groups were examined, and the acidic 5-tetrazolyl group separated from the acetophenone moiety by four to seven methylenes (26, 23, 27, 28) gave excellent in vitro and in vivo activities. Compound 26 (LY171883) had the best balance of in vitro and in vivo activity. It lacked bronchospastic activity at the doses administered and has been chosen for clinical evaluation.

  DOI：

  10.1021/jm00387a018

文献信息

• MARSHALL W. S.; GOODSON T.; CULLINAN G. J.; SWANSON-BEAN D.; HAISCH K. D.+, J. MED. CHEM., 30,(1987) N 4, 682-689
  作者：MARSHALL W. S.、 GOODSON T.、 CULLINAN G. J.、 SWANSON-BEAN D.、 HAISCH K. D.+

  DOI：——

  日期：——
• Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives
  作者：Winston S. Marshall、Theodore Goodson、George J. Cullinan、Dorothy Swanson-Bean、Klaus D. Haisch、Lynn E. Rinkema、Jerome H. Fleisch

  DOI：10.1021/jm00387a018

  日期：1987.4

  A series of derivatives of 2,4-dihydroxy-3-propylacetophenone(1) were prepared and examined for their ability to block leukotriene D4 (LTD4) induced contraction of guinea pig ileum. Straight-chain carboxylic acids where the carboxyl group was separated from the acetophenone moiety by varying numbers of methylenes were evaluated, and maximum activity was obtained with the pentamethylene acid (6). Examination of ring substitution showed that the 2-propyl-3-hydroxy-4-acetyl substitution pattern was required for maximum LTD4 antagonist activity. Additional chain terminal groups were examined, and the acidic 5-tetrazolyl group separated from the acetophenone moiety by four to seven methylenes (26, 23, 27, 28) gave excellent in vitro and in vivo activities. Compound 26 (LY171883) had the best balance of in vitro and in vivo activity. It lacked bronchospastic activity at the doses administered and has been chosen for clinical evaluation.