benzyl {2-methyl-1-[4-(2-phenylethoxy)benzoyl]-1H-indol-4-yl}acetate | 756479-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: benzyl {2-methyl-1-[4-(2-phenylethoxy)benzoyl]-1H-indol-4-yl}acetate
• CAS: 756479-02-4
• 化学式: C₃₃H₂₉NO₄
• 分子量: 503.598
• InChiKey: DWDFVARMTRIBMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl {2-methyl-1-[4-(2-phenylethoxy)benzoyl]-1H-indol-4-yl}acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以58%的产率得到{2-Methyl-1-[4-(2-phenylethoxy)benzoyl]-1H-indol-4-yl}acetic acid
  参考文献：
  名称：

  Development of prostaglandin D2 receptor antagonist: discovery of highly potent antagonists

  摘要：

  The process of discovery for highly potent prostaglandin D-2 (PGD(2)) receptor antagonists is reported. A series of N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acids were synthesized and identified as a new class of selective PGD(2) receptor antagonists. Most of them exhibited strong PGD(2) receptor antagonism in binding studies and the cAMP formation assay. The structure-activity relationships (SAR), including subtype selectivity of the synthesized compounds, are also discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.024
• 作为产物：
  描述：

  1-tert-butoxycarbonyl-2-methyl-1H-indol-4-yl acetic acid 在 四氢吡咯 、 sodium hydroxide 、 四丁基氯化铵 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl {2-methyl-1-[4-(2-phenylethoxy)benzoyl]-1H-indol-4-yl}acetate
  参考文献：
  名称：

  Discovery of orally active prostaglandin D2 receptor antagonists

  摘要：

  A series of N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acids were synthesized and evaluated for prostaglandin D-2 (DP) receptor affinity and antagonist activity. Some of them exhibited strong receptor binding and were potent in the cAMP formation assays. These antagonists also suppressed allergic inflammatory responses such as the PGD(2)-induced increase of microvascular permeability. Structure-activity relationship (SAR) data are presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.039