4-(2-carbazol-9-ylethoxy)phenylamine | 944918-80-3

• 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: 4-(2-carbazol-9-ylethoxy)phenylamine
• 英文别名: 4-(2-Carbazol-9-ylethoxy)aniline；4-(2-carbazol-9-ylethoxy)aniline
• CAS: 944918-80-3
• 化学式: C₂₀H₁₈N₂O
• 分子量: 302.376
• InChiKey: PDHOAHQXUOJRFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-carbazol-9-ylethoxy)phenylamine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.5h， 生成 1-[4-(2-Carbazol-9-ylethoxy)phenyl]-1-(cyclopropylmethyl)urea
  参考文献：
  名称：

  Design and synthesis of urea and thiourea derivatives and their inhibitory activities on lipopolysaccharide-induced NO production

  摘要：

  Series of ureas and thioureas were designed and synthesized, and their inhibitory activities of NO production in lipopolysaccharide-activated macrophages were evaluated. We found several essential moieties in the structure of the prepared compounds for the activity. Thiourea derivatives revealed higher inhibitory activity than the corresponding urea derivatives. Among these compounds, 7e having carboxymethyl group at N3 position of thiourea was the most potent in the inhibition of NO production. They inhibited NO production through the Suppression of NOS protein and mRNA expression. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.005
• 作为产物：
  描述：

  甲磺酸2-咔唑-9-亚乙基酯 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 4-(2-carbazol-9-ylethoxy)phenylamine
  参考文献：
  名称：

  Design and synthesis of urea and thiourea derivatives and their inhibitory activities on lipopolysaccharide-induced NO production

  摘要：

  Series of ureas and thioureas were designed and synthesized, and their inhibitory activities of NO production in lipopolysaccharide-activated macrophages were evaluated. We found several essential moieties in the structure of the prepared compounds for the activity. Thiourea derivatives revealed higher inhibitory activity than the corresponding urea derivatives. Among these compounds, 7e having carboxymethyl group at N3 position of thiourea was the most potent in the inhibition of NO production. They inhibited NO production through the Suppression of NOS protein and mRNA expression. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.005

文献信息

• Synthesis of Heterocycle-linked Thioureas and Their Inhibitory Activities of NO Production in LPS Activated Macrophages
  作者：Ye-Jin Cheon、Hyo-Jin Gim、Hee-Ryun Jang、Jae-Ha Ryu、Raok Jeon

  DOI：10.5012/bkcs.2010.31.01.027

  日期：2010.1.20

  A series of thioureas were synthesized as inhibitors of NO production in lipopolysaccharide-activated macrophages. We investigated the effect of lipophilic moiety and N-substituents of the thioureas on the activity. Phenoxazine and carbazole-containing derivatives revealed higher activity than indole-containing thioureas. The appropriate spacer between lipophilic tail and thiourea head and methyl substituent at N3 position of thiourea brought beneficial effect on the inhibition of NO production. Among prepared compounds, phenoxazine-containing derivative 2a was the most potent with $2.32 \mu}M$ of $IC_50}$ value. RT-PCR analysis suggested that the prepared thioureas inhibited NO production through the suppression of iNOS mRNA expression.

  合成了一系列的硫脲作为脂多糖激活的巨噬细胞中NO产生的抑制剂。我们研究了硫脲的亲脂基团和N取代基对活性的影响。含有苯氧噻嗪和咔唑的衍生物表现出比含有吲哚的硫脲更高的活性。亲脂尾和硫脲头之间适当的间隔，以及在硫脲的N3位置上的甲基取代基对NO产生的抑制效果有利。 在所制备的化合物中，含有苯氧噻嗪的衍生物2a是最有效的，其< TEX>$IC_50}$值为< TEX>$2.32 \mu}M$。RT-PCR分析表明，所制备的硫脲通过抑制iNOS mRNA表达来抑制NO的产生。
• Synthesis of phenylisothiourea derivatives as inhibitors of NO production in LPS activated macrophages
  作者：Guo Hua Jin、Da Yeon Lee、Ye-Jin Cheon、Hyo Jin Gim、Do Hee Kim、Hee-Doo Kim、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2009.04.001

  日期：2009.6

  A series of phenylisothioureas were synthesized as inhibitors of NO production in lipopolysaccharide-activated macrophages. We investigated the effect of lipophilic moiety and N- or S-substituents of the phenylisothioureas on the activity. Inhibitory activities of carbazole-linked phenylisothioureas were superior to the corresponding simple phenylisothiourea derivatives. Among these compounds, 12b having N- ethyl and S-isopropyl groups on phenylisothiourea moiety was the most potent in the inhibition of NO production. They inhibited NO production through the suppression of the LPS-induced translocation of p65 subunit of NF-kappa B and the followed suppression of the iNOS protein and mRNA expression. (C) 2009 Elsevier Ltd. All rights reserved.
• Design and synthesis of carbamate and thiocarbamate derivatives and their inhibitory activities of NO production in LPS activated macrophages
  作者：Guo Hua Jin、Hwa Jin Lee、Hyo Jin Gim、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2012.03.010

  日期：2012.5

  Series of carbamate and thiocarbamate derivatives were designed and synthesized and their inhibitory activities of NO production in lipopolysaccharide-activated macrophages were evaluated. Several thoicarbamate derivatives revealed promising inhibitory activity. The structure-activity relationship study of these compounds is also reported. Among these compounds, compound 12b was the most potent with 6.5 mu M of IC50. They inhibited NO production through the suppression of iNOS protein and mRNA expression and nuclear translocation of p65. (C) 2012 Elsevier Ltd. All rights reserved.
• Design and synthesis of urea and thiourea derivatives and their inhibitory activities on lipopolysaccharide-induced NO production
  作者：Yoon Jung Kim、Jae-Ha Ryu、Ye Jin Cheon、Hyo Jin Lim、Raok Jeon

  DOI：10.1016/j.bmcl.2007.04.005

  日期：2007.6

  Series of ureas and thioureas were designed and synthesized, and their inhibitory activities of NO production in lipopolysaccharide-activated macrophages were evaluated. We found several essential moieties in the structure of the prepared compounds for the activity. Thiourea derivatives revealed higher inhibitory activity than the corresponding urea derivatives. Among these compounds, 7e having carboxymethyl group at N3 position of thiourea was the most potent in the inhibition of NO production. They inhibited NO production through the Suppression of NOS protein and mRNA expression. (c) 2007 Elsevier Ltd. All rights reserved.