4-氯-2,5-二乙氧基苯胺 | 35271-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-氯-2,5-二乙氧基苯胺
• 英文名称: 4-chloro-2,5-diethoxyaniline
• 英文别名: 2,5-diethoxy-4-chloro-aniline；2,5-Diaethoxy-4-chlor-anilin；1-Amino-2,5-diaethoxy-4-chlorbenzol
• CAS: 35271-60-4
• 化学式: C₁₀H₁₄ClNO₂
• 分子量: 215.68
• InChiKey: QKRGVQSQFKCZEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  4-氯-2,5-二乙氧基苯胺 在 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 1-(4-chloro-2,5-diethoxyphenyl)-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-氯-2,5-二乙氧基苯胺
  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

• Klaassens; Schoot, Recueil des Travaux Chimiques des Pays-Bas, 1953, vol. 72, p. 91
  作者：Klaassens、Schoot

  DOI：——

  日期：——
• Arylamides of furoyl-acetic acid
  申请人：DU PONT

  公开号：US02064331A1

  公开（公告）日：1936-12-15
• Modena, Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1956, vol. 14, p. 17,19
  作者：Modena

  DOI：——

  日期：——
• 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.