4-{N-[4-(2-carbazol-9-ylethoxy)phenyl]-N'-ethylcarbamimidoylsulfanylmethyl}benzoic acid methyl ester | 1170007-35-8

• 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-{N-[4-(2-carbazol-9-ylethoxy)phenyl]-N'-ethylcarbamimidoylsulfanylmethyl}benzoic acid methyl ester
• 英文别名: methyl 4-[[N-[4-(2-carbazol-9-ylethoxy)phenyl]-N'-ethylcarbamimidoyl]sulfanylmethyl]benzoate
• CAS: 1170007-35-8
• 化学式: C₃₂H₃₁N₃O₃S
• 分子量: 537.682
• InChiKey: ADPGTGKJVBLULM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  90.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-{N-[4-(2-carbazol-9-ylethoxy)phenyl]-N'-ethylcarbamimidoylsulfanylmethyl}benzoic acid methyl ester 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以45%的产率得到4-{N-[4-(2-carbazol-9-ylethoxy)phenyl]-N'-ethylcarbamimidoylsulfanylmethyl}benzoic acid
  参考文献：
  名称：

  Synthesis of phenylisothiourea derivatives as inhibitors of NO production in LPS activated macrophages

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.04.001
• 作为产物：
  描述：

  1-[4-(2-Carbazol-9-ylethoxy)phenyl]-3-ethylthiourea 、 4-溴甲基苯甲酸甲酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 以70%的产率得到4-{N-[4-(2-carbazol-9-ylethoxy)phenyl]-N'-ethylcarbamimidoylsulfanylmethyl}benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis of phenylisothiourea derivatives as inhibitors of NO production in LPS activated macrophages

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.04.001

文献信息

• 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.