9-(6-Bromohexyl)carbazol-2-ol | 1427205-95-5

• 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: 9-(6-Bromohexyl)carbazol-2-ol
• 英文别名: 9-(6-bromohexyl)carbazol-2-ol
• CAS: 1427205-95-5
• 化学式: C₁₈H₂₀BrNO
• 分子量: 346.267
• InChiKey: MGFALVLTDRLHIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  9-(6-Bromohexyl)carbazol-2-ol 、 5-羟基间苯二甲酸二甲酯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Dimethyl 5-[6-(2-hydroxycarbazol-9-yl)hexoxy]benzene-1,3-dicarboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-alkylcarbazole derivatives as STAT3 inhibitors: Preliminary study

  摘要：

  The signalling pathway of Janus tyrosine Kinases-Signal Transducers and Activators of Transcription (JAK-STAT) is activated by a number of cytokines, hormones (GH, erythropoietin and prolactin), and growth factors. JAR-STAT signalling is involved in regulation of cell proliferation, differentiation and apoptosis. These activities are due to different members of JAR-STAT family consisting of: JAK1, JAK2, JAK3, Tyk2 and STAT1, STA1'2, STAT3, STAT4, STAT5a, STAT5b, STAT6. Recent studies suggest a key role for STAT family proteins, in particular for STAT3, in selectively inducing and maintaining a pro-carcinogenic inflammatory microenvironment, that promote tumour cells transformation. Moreover, a striking correlation between cancer development/progression and STAT3 persistent activation exists, probably due to STAT3 promoting of the pro-oncogenic inflammatory pathways, like NF-kB, IL-6 and JAR family kinases. Recent study demonstrated that carbazoles can inhibit STAT3 mediated transcription. From these evidences, STAT3 represents a therapeutic target, so we have synthesized a new set of N-alkylcarbazole derivatives substituted in positions 2, 4 and 6, to evaluate their activity on STAT3. Some of these compounds showed an interesting activity as STAT3 selective inhibitors; in particular, compounds 9a 9b and 9c revealed to inhibit the STAT3 activation for the 50%, 90% and 95%, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.004
• 作为产物：
  描述：

  1,6-二溴己烷 、 2-羟基咔唑 在 苄基三乙基溴化铵 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 生成 9-(6-Bromohexyl)carbazol-2-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-alkylcarbazole derivatives as STAT3 inhibitors: Preliminary study

  摘要：

  The signalling pathway of Janus tyrosine Kinases-Signal Transducers and Activators of Transcription (JAK-STAT) is activated by a number of cytokines, hormones (GH, erythropoietin and prolactin), and growth factors. JAR-STAT signalling is involved in regulation of cell proliferation, differentiation and apoptosis. These activities are due to different members of JAR-STAT family consisting of: JAK1, JAK2, JAK3, Tyk2 and STAT1, STA1'2, STAT3, STAT4, STAT5a, STAT5b, STAT6. Recent studies suggest a key role for STAT family proteins, in particular for STAT3, in selectively inducing and maintaining a pro-carcinogenic inflammatory microenvironment, that promote tumour cells transformation. Moreover, a striking correlation between cancer development/progression and STAT3 persistent activation exists, probably due to STAT3 promoting of the pro-oncogenic inflammatory pathways, like NF-kB, IL-6 and JAR family kinases. Recent study demonstrated that carbazoles can inhibit STAT3 mediated transcription. From these evidences, STAT3 represents a therapeutic target, so we have synthesized a new set of N-alkylcarbazole derivatives substituted in positions 2, 4 and 6, to evaluate their activity on STAT3. Some of these compounds showed an interesting activity as STAT3 selective inhibitors; in particular, compounds 9a 9b and 9c revealed to inhibit the STAT3 activation for the 50%, 90% and 95%, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.004

文献信息

• Synthesis and biological evaluation of new N-alkylcarbazole derivatives as STAT3 inhibitors: Preliminary study
  作者：Carmela Saturnino、Chiara Palladino、Mariagrazia Napoli、Maria Stefania Sinicropi、Antonio Botta、Marina Sala、Alessandra Carcereri de Prati、Ettore Novellino、Hisanori Suzuki

  DOI：10.1016/j.ejmech.2012.11.004

  日期：2013.2

  The signalling pathway of Janus tyrosine Kinases-Signal Transducers and Activators of Transcription (JAK-STAT) is activated by a number of cytokines, hormones (GH, erythropoietin and prolactin), and growth factors. JAR-STAT signalling is involved in regulation of cell proliferation, differentiation and apoptosis. These activities are due to different members of JAR-STAT family consisting of: JAK1, JAK2, JAK3, Tyk2 and STAT1, STA1'2, STAT3, STAT4, STAT5a, STAT5b, STAT6. Recent studies suggest a key role for STAT family proteins, in particular for STAT3, in selectively inducing and maintaining a pro-carcinogenic inflammatory microenvironment, that promote tumour cells transformation. Moreover, a striking correlation between cancer development/progression and STAT3 persistent activation exists, probably due to STAT3 promoting of the pro-oncogenic inflammatory pathways, like NF-kB, IL-6 and JAR family kinases. Recent study demonstrated that carbazoles can inhibit STAT3 mediated transcription. From these evidences, STAT3 represents a therapeutic target, so we have synthesized a new set of N-alkylcarbazole derivatives substituted in positions 2, 4 and 6, to evaluate their activity on STAT3. Some of these compounds showed an interesting activity as STAT3 selective inhibitors; in particular, compounds 9a 9b and 9c revealed to inhibit the STAT3 activation for the 50%, 90% and 95%, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.