1-[2-hydroxy-4-(3-chloropropoxy)-5-ethylphenyl]ethanone | 156005-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-hydroxy-4-(3-chloropropoxy)-5-ethylphenyl]ethanone
• 英文别名: 1-[4-(3-Chloropropoxy)-5-ethyl-2-hydroxyphenyl]ethanone
• CAS: 156005-61-7
• 化学式: C₁₃H₁₇ClO₃
• 分子量: 256.729
• InChiKey: HMJKKUMPMAZJFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2-hydroxy-4-(3-chloropropoxy)-5-ethylphenyl]ethanone 在 potassium carbonate 、 一水合肼 、 potassium iodide 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 7.0h， 生成 3-(3-{3-[2-Ethyl-5-hydroxy-4-(1H-pyrazol-3-yl)-phenoxy]-propoxy}-4-propyl-phenyl)-propionic acid ethyl ester
  参考文献：
  名称：

  Leukotriene B4 (LTB4) Receptor Antagonists: A Series of (Hydroxyphenyl)pyrazoles

  摘要：

  A series of (hydroxyphenyl)pyrazoles was designed by molecular modeling comparison with the LTB(4) structure and prepared for evaluation as LTB(4) receptor antagonists, culminating in 4-ethyl-5-[[6-methyl-6-(1H-tetrazol-5-yl)heptyl]oxy]-2-(1H-pyrazol-3-yl)phenyl (2). Using an assay for inhibition of specific [H-3]LTB(4) binding to human PMN, it was found that the pyrazole ring could be methylated at N(1) with little loss of activity while methylation at N(2) reduced activity significantly. The structure-activity relationship of the terminal acid group was investigated. Good activity was found with o- and m-phenylalkanoic acids, chromane carboxylic acid, and tetrazole groups. The best in vitro activity was realized with the pyrazole nitrogen unsubstituted and with a six-carbon chain linking the phenyl ether oxygen to the tetrazole group. Compound 2, having an IC50 of 6.4 +/- 0.8 nM in the binding assay, was selected for further preclinical evaluation.

  DOI：

  10.1021/jm00041a021
• 作为产物：
  描述：

  1-(5-乙基-2,4-二羟基苯基)乙酮 、 1-溴-3-氯丙烷 在 potassium carbonate 、 potassium iodide 作用下， 以 丁酮 为溶剂， 反应 72.0h， 生成 1-[2-hydroxy-4-(3-chloropropoxy)-5-ethylphenyl]ethanone
  参考文献：
  名称：

  Leukotriene B4 (LTB4) Receptor Antagonists: A Series of (Hydroxyphenyl)pyrazoles

  摘要：

  A series of (hydroxyphenyl)pyrazoles was designed by molecular modeling comparison with the LTB(4) structure and prepared for evaluation as LTB(4) receptor antagonists, culminating in 4-ethyl-5-[[6-methyl-6-(1H-tetrazol-5-yl)heptyl]oxy]-2-(1H-pyrazol-3-yl)phenyl (2). Using an assay for inhibition of specific [H-3]LTB(4) binding to human PMN, it was found that the pyrazole ring could be methylated at N(1) with little loss of activity while methylation at N(2) reduced activity significantly. The structure-activity relationship of the terminal acid group was investigated. Good activity was found with o- and m-phenylalkanoic acids, chromane carboxylic acid, and tetrazole groups. The best in vitro activity was realized with the pyrazole nitrogen unsubstituted and with a six-carbon chain linking the phenyl ether oxygen to the tetrazole group. Compound 2, having an IC50 of 6.4 +/- 0.8 nM in the binding assay, was selected for further preclinical evaluation.

  DOI：

  10.1021/jm00041a021

文献信息

• Heterocycle substituted diphenyl leukotriene antagonists
  申请人：Eli Lilly and Company

  公开号：US06797723B1

  公开（公告）日：2004-09-28

  The invention relates to novel heterocycle substituted diphenyl leukotriene B4 (LTB4) antagonists, to compositions containing such compounds, and to methods of using such compounds for treatment of inflammatory diseases.

  本发明涉及新颖的杂环取代的二苯基白三烯B4（LTB4）拮抗剂，涉及含有此类化合物的组合物，以及使用此类化合物治疗炎症性疾病的方法。
• US6797723B1
  申请人：——

  公开号：US6797723B1

  公开（公告）日：2004-09-28
• [EN] ONCOLYTIC COMBINATIONS FOR THE TREATMENT OF CANCER<br/>[FR] COMBINAISONS ONCOLYTIQUES POUR TRAITEMENT DES CANCERS
  申请人：LILLY CO ELI

  公开号：WO2001034198A2

  公开（公告）日：2001-05-17

  Leukotriene (LTB4) antagonists enhance the effectiveness of 2',2'-difluoronucleoside anti-cancer agents.
• Leukotriene B4 (LTB4) Receptor Antagonists: A Series of (Hydroxyphenyl)pyrazoles
  作者：Richard W. Harper、William T. Jackson、Larry L. Froelich、Robert J. Boyd、Timothy E. Aldridge、David K. Herron

  DOI：10.1021/jm00041a021

  日期：1994.7

  A series of (hydroxyphenyl)pyrazoles was designed by molecular modeling comparison with the LTB(4) structure and prepared for evaluation as LTB(4) receptor antagonists, culminating in 4-ethyl-5-[[6-methyl-6-(1H-tetrazol-5-yl)heptyl]oxy]-2-(1H-pyrazol-3-yl)phenyl (2). Using an assay for inhibition of specific [H-3]LTB(4) binding to human PMN, it was found that the pyrazole ring could be methylated at N(1) with little loss of activity while methylation at N(2) reduced activity significantly. The structure-activity relationship of the terminal acid group was investigated. Good activity was found with o- and m-phenylalkanoic acids, chromane carboxylic acid, and tetrazole groups. The best in vitro activity was realized with the pyrazole nitrogen unsubstituted and with a six-carbon chain linking the phenyl ether oxygen to the tetrazole group. Compound 2, having an IC50 of 6.4 +/- 0.8 nM in the binding assay, was selected for further preclinical evaluation.