1-乙基-3-(萘-2-基)脲 | 1067239-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-乙基-3-(萘-2-基)脲
• 英文名称: 1-ethyl-3-(naphthalen-2-yl)urea
• 英文别名: N-ethyl-N'-[2]naphthyl-urea；N-Aethyl-N'-[2]naphthyl-harnstoff；1-Ethyl-3-naphthalen-2-ylurea；1-ethyl-3-naphthalen-2-ylurea
• CAS: 1067239-59-1
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: NDUMSXBMMDPPKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-乙基-3-(萘-2-基)脲 在 乙醇 、 氨 、 硝酸 作用下， 生成 1,6,8-trinitro-[2]naphthylamine
  参考文献：
  名称：

  Groeneveld, Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 783,796,797,803

  摘要：

  DOI：
• 作为产物：
  描述：

  2-萘胺 、 异氰酸乙酯 以 二氯甲烷 为溶剂， 以50%的产率得到1-乙基-3-(萘-2-基)脲
  参考文献：
  名称：

  Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression

  摘要：

  Recently, a subset of N-phenyl-N'-(2-chloroethyl) ureas (CEU) was found abrogating the nuclear translocation of thioredoxin-1 and arresting the cell cycle in G(0)/G(1) phase. Several derivatives were prepared to assess their effect on cell cycle progression and on the intracellular location of Trx-1. Compounds 1-20, 21-40, and 41-60 exhibited GI(50) between 1 and 80 mu M. Immunocytochemistry analysis showed compounds 4, 6, 8, 10, 11, 23, 24, 26-31, 34, 37, 41, 44, 46-51, 53, 56, and 57 inhibiting the nuclear translocation of Trx-1. Our results suggest that increasing the electrophilic character of these molecules might enhance the antiproliferative activity at the expense of the selectivity toward thioredoxin-1 and the G(0)/G(1) phase arrest. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.006

文献信息

• US7662910B2
  申请人：——

  公开号：US7662910B2

  公开（公告）日：2010-02-16
• Groeneveld, Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 783,796,797,803
  作者：Groeneveld

  DOI：——

  日期：——
• Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression
  作者：Jessica S. Fortin、Marie-France Côté、Jacques Lacroix、Éric Petitclerc、René C.-Gaudreault

  DOI：10.1016/j.bmc.2008.06.006

  日期：2008.8

  Recently, a subset of N-phenyl-N'-(2-chloroethyl) ureas (CEU) was found abrogating the nuclear translocation of thioredoxin-1 and arresting the cell cycle in G(0)/G(1) phase. Several derivatives were prepared to assess their effect on cell cycle progression and on the intracellular location of Trx-1. Compounds 1-20, 21-40, and 41-60 exhibited GI(50) between 1 and 80 mu M. Immunocytochemistry analysis showed compounds 4, 6, 8, 10, 11, 23, 24, 26-31, 34, 37, 41, 44, 46-51, 53, 56, and 57 inhibiting the nuclear translocation of Trx-1. Our results suggest that increasing the electrophilic character of these molecules might enhance the antiproliferative activity at the expense of the selectivity toward thioredoxin-1 and the G(0)/G(1) phase arrest. (C) 2008 Elsevier Ltd. All rights reserved.