1-ethyl-4-(3-methyl-4-nitrophenyl)piperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-ethyl-4-(3-methyl-4-nitrophenyl)piperazine
• 化学式: C₁₃H₁₉N₃O₂
• 分子量: 249.313
• InChiKey: IVWXQPIDTPGYIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ethyl-4-(3-methyl-4-nitrophenyl)piperazine 在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到4-(4-乙基-1-哌嗪基)-2-甲基苯胺
  参考文献：
  名称：

  Optimization of the phenylurea moiety in a phosphoinositide 3-kinase (PI3K) inhibitor to improve water solubility and the PK profile by introducing a solubilizing group and ortho substituents

  摘要：

  Phosphoinositide 3-kinase (PI3K) is a promising anti-cancer target, because various mutations and amplifications are observed in human tumors isolated from cancer patients. Our dihydropyrrolopyrimidine derivative with a phenylurea moiety showed strong PI3K enzyme inhibitory activity, but its pharmacokinetic property was poor because of lack of solubility. Herein, we report how we improved the solubility of our PI3K inhibitors by introducing a solubilizing group and ortho substituents to break molecular planarity. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2016.04.060
• 作为产物：
  描述：

  N-乙基哌嗪 、 5-氟-2-硝基甲苯 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 生成 1-ethyl-4-(3-methyl-4-nitrophenyl)piperazine
  参考文献：
  名称：

  Optimization of the phenylurea moiety in a phosphoinositide 3-kinase (PI3K) inhibitor to improve water solubility and the PK profile by introducing a solubilizing group and ortho substituents

  摘要：

  Phosphoinositide 3-kinase (PI3K) is a promising anti-cancer target, because various mutations and amplifications are observed in human tumors isolated from cancer patients. Our dihydropyrrolopyrimidine derivative with a phenylurea moiety showed strong PI3K enzyme inhibitory activity, but its pharmacokinetic property was poor because of lack of solubility. Herein, we report how we improved the solubility of our PI3K inhibitors by introducing a solubilizing group and ortho substituents to break molecular planarity. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2016.04.060

文献信息

• Optimization of the phenylurea moiety in a phosphoinositide 3-kinase (PI3K) inhibitor to improve water solubility and the PK profile by introducing a solubilizing group and ortho substituents
  作者：Hatsuo Kawada、Hirosato Ebiike、Masao Tsukazaki、Shun Yamamoto、Kohei Koyama、Mitsuaki Nakamura、Kenji Morikami、Kiyoshi Yoshinari、Miyuki Yoshida、Kotaro Ogawa、Nobuo Shimma、Takuo Tsukuda、Jun Ohwada

  DOI：10.1016/j.bmc.2016.04.060

  日期：2016.7

  Phosphoinositide 3-kinase (PI3K) is a promising anti-cancer target, because various mutations and amplifications are observed in human tumors isolated from cancer patients. Our dihydropyrrolopyrimidine derivative with a phenylurea moiety showed strong PI3K enzyme inhibitory activity, but its pharmacokinetic property was poor because of lack of solubility. Herein, we report how we improved the solubility of our PI3K inhibitors by introducing a solubilizing group and ortho substituents to break molecular planarity. (C) 2016 Published by Elsevier Ltd.