N-[6-(4'-acetyl-3'-hydroxy-2'-propylphenoxy)hexyl]morpholine | 92518-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[6-(4'-acetyl-3'-hydroxy-2'-propylphenoxy)hexyl]morpholine
• 英文别名: 1-[2-Hydroxy-4-(6-morpholin-4-ylhexoxy)-3-propylphenyl]ethanone
• CAS: 92518-47-3
• 化学式: C₂₁H₃₃NO₄
• 分子量: 363.497
• InChiKey: ZGDANTDXRZKOHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二羟基-3-丙基苯乙酮 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 34.0h， 生成 N-[6-(4'-acetyl-3'-hydroxy-2'-propylphenoxy)hexyl]morpholine
  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, WINSTON S.;VERGE, JOHN P.
  作者：MARSHALL, WINSTON S.、VERGE, JOHN P.

  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.