1-(2-金刚烷基)-3-(2-氯乙基)脲 | 33082-90-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 中文名称: 1-(2-金刚烷基)-3-(2-氯乙基)脲
• 英文名称: 1-adamantan-2-yl-3-(2-chloroethyl)urea
• 英文别名: N-Adamantan-2-yl-N'-<2-chlor-aethyl>-harnstoff；1-(2-Chloroethyl)-3-tricyclo[3.3.1.13,7]dec-2-ylurea；1-(2-adamantyl)-3-(2-chloroethyl)urea
• CAS: 33082-90-5
• 化学式: C₁₃H₂₁ClN₂O
• 分子量: 256.776
• InChiKey: DVTGTPJRYOAKQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 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-(2-金刚烷基)-3-(2-氯乙基)脲 在 KF on SiO₂ 作用下， 以 乙腈 为溶剂， 以98%的产率得到N-(1-adamantan-2-yl)-4,5-dihydroxyoxazol-2-amine
  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
• 作为产物：
  描述：

  氯乙基异氰酸酯 、 2-氨基金刚烷 生成 1-(2-金刚烷基)-3-(2-氯乙基)脲
  参考文献：
  名称：

  合成潜在的抗癌药。38. N-亚硝基脲。4.卤代乙基衍生物的进一步合成和评价。

  摘要：

  DOI：

  10.1021/jm00289a011

文献信息

• Synthesis of potential anticancer agents. 38. N-nitrosoureas. 4. Further synthesis and evaluation of haloethyl derivatives
  作者：Thomas P. Johnston、George S. McCaler、Pamela S. Opliger、W. Russell Laster、John A. Montgomery

  DOI：10.1021/jm00289a011

  日期：1971.7
• 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.