1-(3,5-Dimethylphenyl)indol-5-ol | 852042-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(3,5-Dimethylphenyl)indol-5-ol
• 英文别名: 1-(3,5-dimethylphenyl)indol-5-ol
• CAS: 852042-13-8
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: CDBZDRXZTWRPJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  429.7±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,5-Dimethylphenyl)indol-5-ol 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 生成 1-(3,5-dimethylphenyl)-2,3-dihydroindol-5-ol
  参考文献：
  名称：

  Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide

  摘要：

  A series of substituted indoline and indole derivatives with cyclooxygenase (COX)-inhibitory activity was prepared during our structural development studies based on thalidomide as a multi-template lead compound. Structure-activity relationship studies indicated that the nature of the substituent introduced at the benzene ring of the indoline (indole) backbone, and the length and type of the linking group between the nitrogen atom of indoline (indole) and the N-substituent are important for the activity. This study has led to the identification of COX-1-selective inhibitors, and these should be useful not only as pharmacological tools to investigate the physiology and pathophysiology of COX, but also as sophisticated leads for the development of novel drugs to treat COX-associated diseases, such as inflammatory diseases, and cancer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.002
• 作为产物：
  描述：

  5-苄氧基吲哚 在 palladium on activated charcoal 3 A molecular sieve 、 氢气 、 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 1-(3,5-Dimethylphenyl)indol-5-ol
  参考文献：
  名称：

  Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide

  摘要：

  A series of substituted indoline and indole derivatives with cyclooxygenase (COX)-inhibitory activity was prepared during our structural development studies based on thalidomide as a multi-template lead compound. Structure-activity relationship studies indicated that the nature of the substituent introduced at the benzene ring of the indoline (indole) backbone, and the length and type of the linking group between the nitrogen atom of indoline (indole) and the N-substituent are important for the activity. This study has led to the identification of COX-1-selective inhibitors, and these should be useful not only as pharmacological tools to investigate the physiology and pathophysiology of COX, but also as sophisticated leads for the development of novel drugs to treat COX-associated diseases, such as inflammatory diseases, and cancer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.002

文献信息

• Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide
  作者：Hiroko Sano、Tomomi Noguchi、Aya Tanatani、Yuichi Hashimoto、Hiroyuki Miyachi

  DOI：10.1016/j.bmc.2005.03.002

  日期：2005.5

  A series of substituted indoline and indole derivatives with cyclooxygenase (COX)-inhibitory activity was prepared during our structural development studies based on thalidomide as a multi-template lead compound. Structure-activity relationship studies indicated that the nature of the substituent introduced at the benzene ring of the indoline (indole) backbone, and the length and type of the linking group between the nitrogen atom of indoline (indole) and the N-substituent are important for the activity. This study has led to the identification of COX-1-selective inhibitors, and these should be useful not only as pharmacological tools to investigate the physiology and pathophysiology of COX, but also as sophisticated leads for the development of novel drugs to treat COX-associated diseases, such as inflammatory diseases, and cancer. (c) 2005 Elsevier Ltd. All rights reserved.