1-(9-ethyl-9H-carbazol-3-yl)-3-phenylthiourea

• 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: 1-(9-ethyl-9H-carbazol-3-yl)-3-phenylthiourea
• 英文别名: 1-(9-ethyl-9H-carbazol-6-yl)-3-phenylthiourea；1-(9-Ethylcarbazol-3-yl)-3-phenylthiourea
• 化学式: C₂₁H₁₉N₃S
• 分子量: 345.468
• InChiKey: ZGLSEGDGVRPZFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(9-ethyl-9H-carbazol-3-yl)-3-phenylthiourea 在 Montmorillonite K₁₀ clay 、 对甲苯磺酸 作用下， 反应 6.0h， 以69%的产率得到6-ethyl-N-phenyl-[1,3]thiazolo[4,5-c]carbazol-2-amine
  参考文献：
  名称：

  A clay-mediated, regioselective synthesis of 2-(aryl/alkyl)amino-thiazolo[4,5-c]carbazoles

  摘要：

  The 3-aminocarbazoles la-e were condensed with phenyl and benzyl isothiocyanates on montmorillonite K10 clay or TLC-grade silica gel at room temperature to furnish efficiently the N-phenyl and N-benzylthioureidocarbazoles, 2a-e and 2f, respectively. within minutes. When adsorbed on montmorillonite K 10 clay impregnated with para-toluene sulfonic acid (1:1, w/w) and heated at 60-70degreesC. 2a-e and 2f furnished the 2-anilino and 2-benzylaminothiazolo[4,5-c]carbazoles, 3a-e and 3f, respectively, regioselectively in high yields. The cyclisation was also effective for the N-methylthioureidocarbazoles 2g-i. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.129
• 作为产物：
  描述：

  3-氨基-9-乙基咔唑 、 硫代异氰酸苯酯 以 甲苯 为溶剂， 以74%的产率得到1-(9-ethyl-9H-carbazol-3-yl)-3-phenylthiourea
  参考文献：
  名称：

  Zika NS5 甲基转移酶和病毒复制的 N,N'-咔唑酰基-芳基-脲抑制剂的设计、合成和发现。

  摘要：

  最近在全球范围内爆发的寨卡病毒（ZIKV）感染使发现针对黄病毒的新型抗病毒药物成为研究重点。这项工作描述了使用 ZIKV NS5-MTase 通过基于结构的虚拟筛选方法鉴定新型 ZIKV 抑制剂。已经发现了一系列具有咔唑基-芳基-脲结构的新型分子，并合成了类似物库。新化合物抑制 ZIKV MTase，IC50 介于 23-48 μM 之间。此外，咔唑酰基芳基脲也被证明可以在微摩尔浓度下抑制 ZIKV 复制活性。

  DOI：

  10.1002/cmdc.201900533

文献信息

• Synthesis, cytotoxic evaluation, molecular docking studies and drug-likeness analysis of some novel 2-[(9-ethyl-9 <i>H</i> -carbazol-3-yl)imino]thiazoles/thiazolidinones
  作者：Noha M. Hassanin、Tarik E. Ali、Somaia M. Abdel-Kariem

  DOI：10.1080/17415993.2024.2302013

  日期：2024.3.3

  A novel series of some 2-[(9-ethyl-9H-carbazol-3-yl)imino]thiazoles/thiazolidinones was synthesized and established by spectroscopic tools and elemental analysis. The synthetic strategy depended on...

  通过光谱工具和元素分析合成并建立了一系列新型2-[(9-乙基-9H-咔唑-3-基)亚氨基]噻唑/噻唑烷酮。合成策略取决于...
• Synthesis and Biological Assessment of Carbazole Linked Pyrazole Schiff bases and Diarylthiourea Derivatives
  作者：Gopinath D. Shirole、Gajanan R. Pandhare、Anil G. Gadhave、Bhagawat K. Uphade、Dilip S. Aute、Vijay A. Kadnor

  DOI：10.5562/cca3700

  日期：——
• Design, Synthesis and Discovery of <i>N,N’</i> ‐Carbazoyl‐aryl‐urea Inhibitors of Zika NS5 Methyltransferase and Virus Replication
  作者：Sharon Spizzichino、Giulio Mattedi、Kate Lauder、Coralie Valle、Wahiba Aouadi、Bruno Canard、Etienne Decroly、Suzanne J. F. Kaptein、Johan Neyts、Carl Graham、Zakary Sule、David J. Barlow、Romano Silvestri、Daniele Castagnolo

  DOI：10.1002/cmdc.201900533

  日期：2020.2.17

  The recent outbreaks of Zika virus (ZIKV) infection worldwide make the discovery of novel antivirals against flaviviruses a research priority. This work describes the identification of novel inhibitors of ZIKV through a structure-based virtual screening approach using the ZIKV NS5-MTase. A novel series of molecules with a carbazoyl-aryl-urea structure has been discovered and a library of analogues

  最近在全球范围内爆发的寨卡病毒（ZIKV）感染使发现针对黄病毒的新型抗病毒药物成为研究重点。这项工作描述了使用 ZIKV NS5-MTase 通过基于结构的虚拟筛选方法鉴定新型 ZIKV 抑制剂。已经发现了一系列具有咔唑基-芳基-脲结构的新型分子，并合成了类似物库。新化合物抑制 ZIKV MTase，IC50 介于 23-48 μM 之间。此外，咔唑酰基芳基脲也被证明可以在微摩尔浓度下抑制 ZIKV 复制活性。
• A clay-mediated, regioselective synthesis of 2-(aryl/alkyl)amino-thiazolo[4,5-c]carbazoles
  作者：Manas Chakrabarty、Nandita Ghosh、Yoshihiro Harigaya

  DOI：10.1016/j.tetlet.2004.04.129

  日期：2004.6

  The 3-aminocarbazoles la-e were condensed with phenyl and benzyl isothiocyanates on montmorillonite K10 clay or TLC-grade silica gel at room temperature to furnish efficiently the N-phenyl and N-benzylthioureidocarbazoles, 2a-e and 2f, respectively. within minutes. When adsorbed on montmorillonite K 10 clay impregnated with para-toluene sulfonic acid (1:1, w/w) and heated at 60-70degreesC. 2a-e and 2f furnished the 2-anilino and 2-benzylaminothiazolo[4,5-c]carbazoles, 3a-e and 3f, respectively, regioselectively in high yields. The cyclisation was also effective for the N-methylthioureidocarbazoles 2g-i. (C) 2004 Elsevier Ltd. All rights reserved.