9-ethyl-4-hydroxy-9H-carbazole | 188941-47-1

• 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-ethyl-4-hydroxy-9H-carbazole
• 英文别名: 9-Ethylcarbazol-4-ol
• CAS: 188941-47-1
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: VAQTVYMSLBECQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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-ethyl-4-hydroxy-9H-carbazole 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 溴 、 碳酸氢钠 作用下， 以 乙醇 、 溶剂黄146 、 丙酮 为溶剂， 反应 47.83h， 生成 10-Ethyl-3-methyl-5H-pyrido[2,3-b]carbazole-5,11(10H)-dione
  参考文献：
  名称：

  Regiospecific Hetero Diels-Alder Synthesis of Pyrido[2,3-b]- and Pyrido[3,2-b]carbazole-5,11-diones

  摘要：

  DOI：

  10.3987/com-96-7722
• 作为产物：
  描述：

  9-ethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 1.0h， 以71%的产率得到9-ethyl-4-hydroxy-9H-carbazole
  参考文献：
  名称：

  Regiospecific Hetero Diels-Alder Synthesis of Pyrido[2,3-b]- and Pyrido[3,2-b]carbazole-5,11-diones

  摘要：

  DOI：

  10.3987/com-96-7722

文献信息

• Biologically active carbazole derivatives: focus on oxazinocarbazoles and related compounds
  作者：Zouhair Bouaziz、Samar Issa、Jacques Gentili、Andreas Gratz、Andre Bollacke、Matthias Kassack、Joachim Jose、Lars Herfindal、Gro Gausdal、Stein Ove Døskeland、Catherine Mullié、Pascal Sonnet、Camille Desgrouas、Nicolas Taudon、Glaucio Valdameri、Attilio Di Pietro、Milad Baitiche、Marc Le Borgne

  DOI：10.3109/14756366.2014.899594

  日期：2015.3.4

  Four series of carbazole derivatives, including N-substituted-hydroxycarbazoles, oxazinocarbazoles, isoxazolocarbazolequinones, and pyridocarbazolequinones, were studied using diverse biological test methods such as a CE-based assay for CK2 activity measurement, a cytotoxicity assay with IPC-81 cell line, determination of MIC of carbazole derivatives as antibacterial agents, a Plasmodium falciparum

  使用多种生物学测试方法研究了四个系列的咔唑衍生物，包括N-取代的羟基咔唑，恶唑并咔唑，异恶唑并咔唑醌和吡啶并咔唑醌，例如基于CE的CK2活性测定，IPC-81细胞系的细胞毒性测定，测定咔唑衍生物作为抗菌剂的MIC，恶性疟原虫药敏试验和ABCG2介导的米托蒽醌测定。两种恶嗪咔唑Ib和Ig均显示出CK2抑制，IC50分别为8.7和14.0 µM。实现了进一步的化学合成，并且7-异丙基恶嗪基咔唑衍生物2对CK2表现出更强的活性（IC50 = 1.40 µM）。恶嗪咔唑Ib，Ig，然后对2和2分别针对IPC-81白血病细胞进行了测试，并显示出诱导白血病细胞死亡的能力，IC50值为57至62μM。还报道了有关抗菌和抗疟原虫活性的进一步研究。没有检测到对ABCG2外排泵有明显的抑制活性。
• Synthesis and antiproliferative activity of oxazinocarbazole and N,N-bis(carbazolylmethyl)amine derivatives
  作者：Samar Issa、Nadia Walchshofer、Issam Kassab、Hussein Termoss、Soulaima Chamat、Aziz Geahchan、Zouhair Bouaziz

  DOI：10.1016/j.ejmech.2010.02.045

  日期：2010.6

  The synthesis, structure elucidation and antitumoral activity of novel heterocyclic compounds containing a carbazole nucleus are reported. Oxazinocarbazoles were synthesized by application of the Mannich reaction to the corresponding hydroxylated derivatives leading to 41 new molecules. Their cytotoxic activity was evaluated against various human tumor cell lines including three leukemic cell lines: CEM and Jurkat (type T), Raji (type B), breast cancer cell line (MCF-7), colorectal cancer cell line (Caco-2).A primary screening at 100 mu M allowed the selection of the 10 most active compounds, which showed an antiproliferative activity on all the cell lines. A dose-effect study between 12.5 and 100 mu M sorted two compounds with a significant activity: 5t and 7e against leukemic cell lines CEM. Jurkat and Raji with IC(50) values around 12 mu M.