4-chloro-2,5-dipropoxyaniline | 123444-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-chloro-2,5-dipropoxyaniline
• CAS: 123444-47-3
• 化学式: C₁₂H₁₈ClNO₂
• 分子量: 243.733
• InChiKey: JFPNSEGKSYAPJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-2,5-dipropoxyaniline 在 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 1-(4-chloro-2,5-dipropoxyphenyl)-3-(3-propoxypropyl)thiourea
  参考文献：
  名称：

  Structure–activity relationship studies of 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, a non-nucleoside reverse transcriptase inhibitor of human immunodeficiency virus type-1

  摘要：

  The reverse transcriptase (RT) of the human immunodeficiency virus type-1 (HIV-1) is still a prime target for drug development due to the continuing need to block drug-resistant RT mutants by new inhibitors. We have previously identified 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, compound 1, as a potent RI inhibitor from an available chemical library. Here, we further modified this compound to study structure activity relationships when replacing various groups in the molecule. Different functional groups were systematically introduced on the aromatic ring and the aliphatic chain of the compound was modified. The effect of these modifications on viral infectivity was then evaluated. The most potent compound found was propyl 4-(amino-N-(4-chloro-2,5-dimethoxyphenyl)methanethioamino)butanoate, 45c, which inhibited infectivity with a calculated IC50 of about 1.1 mu M. Docking studies identified potential important interactions between the top scoring ligands and HIV-1 RT, and the predicted relative affinity of the ligands was found to be in agreement with the experimental results. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.003
• 作为产物：
  描述：

  氯氢醌 在 HNO₃-SiO₂ 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 64.0h， 生成 4-chloro-2,5-dipropoxyaniline
  参考文献：
  名称：

  Structure–activity relationship studies of 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, a non-nucleoside reverse transcriptase inhibitor of human immunodeficiency virus type-1

  摘要：

  The reverse transcriptase (RT) of the human immunodeficiency virus type-1 (HIV-1) is still a prime target for drug development due to the continuing need to block drug-resistant RT mutants by new inhibitors. We have previously identified 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, compound 1, as a potent RI inhibitor from an available chemical library. Here, we further modified this compound to study structure activity relationships when replacing various groups in the molecule. Different functional groups were systematically introduced on the aromatic ring and the aliphatic chain of the compound was modified. The effect of these modifications on viral infectivity was then evaluated. The most potent compound found was propyl 4-(amino-N-(4-chloro-2,5-dimethoxyphenyl)methanethioamino)butanoate, 45c, which inhibited infectivity with a calculated IC50 of about 1.1 mu M. Docking studies identified potential important interactions between the top scoring ligands and HIV-1 RT, and the predicted relative affinity of the ligands was found to be in agreement with the experimental results. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.003

文献信息

• Verfahren zur Herstellung wasserunlöslicher Azofarbstoffe auf der Faser
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0312003A2

  公开（公告）日：1989-04-19

  Gemäß den Färbeweisen dr Eisfarbentechnik werden Fasermaterialien, wie beispielsweise Cellulosefasermaterialien, gefärbt, indem man das mit einer Kupplungskomponente grundierte Fasermaterial in wäßrigem Medium mit der Diazoniumverbindung einer Anilinverbindung der nachstehend angegebenen und definierten allgemeinen Formel (1) kuppelt, wobei die Kupplungsreaktion und Farbstoffbildung auf der Faser bei einem pH-Wert zwischen 3 und 10 durchgeführt wird. in welcher R für eine geradkettige oder verzweigte Alkylgruppe von 3 oder 4 C-Atomen steht.

  根据冰染技术的染色方法，纤维材料（如纤维素纤维材料）的染色是通过在水介质中将用偶联组分打底的纤维材料与下文给出并定义的通式（1）的苯胺化合物的重氮化合物偶联，偶联反应和染料在纤维上的形成是在 pH 值介于 3 和 10 之间的条件下进行的。 其中 R 为 3 或 4 个碳原子的直链或支链烷基。
• US4906250A
  申请人：——

  公开号：US4906250A

  公开（公告）日：1990-03-06
• Structure–activity relationship studies of 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, a non-nucleoside reverse transcriptase inhibitor of human immunodeficiency virus type-1
  作者：Michal Weitman、Keti Lerman、Abraham Nudelman、Dan Thomas Major、Amnon Hizi、Alon Herschhorn

  DOI：10.1016/j.ejmech.2010.11.003

  日期：2011.2

  The reverse transcriptase (RT) of the human immunodeficiency virus type-1 (HIV-1) is still a prime target for drug development due to the continuing need to block drug-resistant RT mutants by new inhibitors. We have previously identified 1-(4-chloro-2,5-dimethoxyphenyl)-3-(3-propoxypropyl)thiourea, compound 1, as a potent RI inhibitor from an available chemical library. Here, we further modified this compound to study structure activity relationships when replacing various groups in the molecule. Different functional groups were systematically introduced on the aromatic ring and the aliphatic chain of the compound was modified. The effect of these modifications on viral infectivity was then evaluated. The most potent compound found was propyl 4-(amino-N-(4-chloro-2,5-dimethoxyphenyl)methanethioamino)butanoate, 45c, which inhibited infectivity with a calculated IC50 of about 1.1 mu M. Docking studies identified potential important interactions between the top scoring ligands and HIV-1 RT, and the predicted relative affinity of the ligands was found to be in agreement with the experimental results. (C) 2010 Elsevier Masson SAS. All rights reserved.