2-Chloro-5-hydroxy-1-(4-hydroxy-benzyl)-6-methyl-1H-indole-3-carboxylic acid | 777858-08-9

• 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: 2-Chloro-5-hydroxy-1-(4-hydroxy-benzyl)-6-methyl-1H-indole-3-carboxylic acid
• 英文别名: 2-Chloro-5-hydroxy-1-[(4-hydroxyphenyl)methyl]-6-methylindole-3-carboxylic acid
• CAS: 777858-08-9
• 化学式: C₁₇H₁₄ClNO₄
• 分子量: 331.755
• InChiKey: VGFIMSIFRFECPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Chloro-5-hydroxy-1-(4-hydroxy-benzyl)-6-methyl-1H-indole-3-carboxylic acid 、 乙酸酐 在 硫酸 作用下， 反应 0.25h， 生成 5-Acetoxy-1-(4-acetoxy-benzyl)-2-chloro-6-methyl-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  N-Benzyl-2-chloroindole-3-carboxylic acids as potential anti-inflammatory agents. Synthesis and screening for the effects on human neutrophil functions and on COX1/COX2 activity

  摘要：

  The synthesis of N-benzyi-2-chloroindole-3-carboxylic acids related to indomethacin is reported. These compounds were tested on in vitro human neutrophil activation. Some of them, more soluble in water, were tested to define the influence on prostaglandin biosynthesis via inhibition of cyclooxygenases (COX1 and COX2) by a chemiluminescent method suitable for fast screening. Several derivatives showed inhibitory effects and in some cases were more active than the parent compound. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.06.008
• 作为产物：
  描述：

  2-氯-5-甲氧基-6-甲基-1H-吲哚-3-甲醛 在 potassium permanganate 、 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 0.34h， 生成 2-Chloro-5-hydroxy-1-(4-hydroxy-benzyl)-6-methyl-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  N-Benzyl-2-chloroindole-3-carboxylic acids as potential anti-inflammatory agents. Synthesis and screening for the effects on human neutrophil functions and on COX1/COX2 activity

  摘要：

  The synthesis of N-benzyi-2-chloroindole-3-carboxylic acids related to indomethacin is reported. These compounds were tested on in vitro human neutrophil activation. Some of them, more soluble in water, were tested to define the influence on prostaglandin biosynthesis via inhibition of cyclooxygenases (COX1 and COX2) by a chemiluminescent method suitable for fast screening. Several derivatives showed inhibitory effects and in some cases were more active than the parent compound. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.06.008

文献信息

• N-Benzyl-2-chloroindole-3-carboxylic acids as potential anti-inflammatory agents. Synthesis and screening for the effects on human neutrophil functions and on COX1/COX2 activity
  作者：Aldo Andreani、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Aldo Roda、Massimo Guardigli、Serena Traniello、Susanna Spisani

  DOI：10.1016/j.ejmech.2004.06.008

  日期：2004.9

  The synthesis of N-benzyi-2-chloroindole-3-carboxylic acids related to indomethacin is reported. These compounds were tested on in vitro human neutrophil activation. Some of them, more soluble in water, were tested to define the influence on prostaglandin biosynthesis via inhibition of cyclooxygenases (COX1 and COX2) by a chemiluminescent method suitable for fast screening. Several derivatives showed inhibitory effects and in some cases were more active than the parent compound. (C) 2004 Elsevier SAS. All rights reserved.