1-(biphenyl-4-yl)-3-(2-chloroethyl)urea | 803729-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(biphenyl-4-yl)-3-(2-chloroethyl)urea
• 英文别名: 1-(2-Chloroethyl)-3-(4-phenylphenyl)urea
• CAS: 803729-55-7
• 化学式: C₁₅H₁₅ClN₂O
• 分子量: 274.75
• InChiKey: OWJDRIAQLQIVDG-UHFFFAOYSA-N

物化性质

• 熔点：
  181-186 °C
• 沸点：
  413.8±45.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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-(biphenyl-4-yl)-3-(2-chloroethyl)urea 在 KF on SiO₂ 作用下， 以 乙腈 为溶剂， 以98%的产率得到N-(4-phenylphenyl)-4,5-dihydro-1,3-oxazol-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 、 4-氨基联苯 以 二氯甲烷 为溶剂， 以91%的产率得到1-(biphenyl-4-yl)-3-(2-chloroethyl)urea
  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

• [EN] HALOETHYL UREA COMPOUNDS AND THEIR USE TO ATTENUATE, INHIBIT OR PREVENT NON-CANCEROUS PATHOGENIC CELLULAR PROLIFERATION AND DISEASES ASSOCIATED THEREWITH<br/>[FR] COMPOSES D'UREE HALOETHYLE ET LEUR UTILISATION EN VUE D'ATTENUER, D'INHIBER OU DE PREVENIR LA PROLIFERATION CELLULAIRE PATHOGENE NON CANCEREUSE ET LES MALADIES Y ETANT ASSOCIEES
  申请人：IMOTEP INC

  公开号：WO2004106292A1

  公开（公告）日：2004-12-09

  The present invention provides haloethyl urea compounds as described in Formula (I) and their use as anti-proliferative agent in the attenuation, inhibition, or prevention of non-cancerous cellular proliferation. These compounds are also provided for use as a therapeutic agent in the treatment of a disease or disorder, wherein pathogenesis of said disease or disorder is associated with non-cancerous pathogenic cellular proliferation.

  本发明提供了如公式(I)所述的卤乙基脲化合物，以及它们作为抗增殖剂在减轻、抑制或预防非癌细胞增殖中的用途。这些化合物还可用作治疗剂，用于治疗与非癌病理性细胞增殖相关的疾病或障碍，其中该疾病或障碍的发病机制与非癌病理性细胞增殖有关。
• [EN] HALOETHYL UREA COMPOUNDS AND THE USE THEREOF TO ATTENUATE, INHIBIT OR PREVENT CANCER CELL MIGRATION<br/>[FR] COMPOSES D'UREE HALOETHYLE ET LEUR UTILISATION EN VUE D'ATTENUER, D'INHIBER OU DE PREVENIR LA MIGRATION DE CELLULES CANCEREUSES
  申请人：IMOTEP INC

  公开号：WO2004106291A1

  公开（公告）日：2004-12-09

  The present invention provides haloethyl urea compounds as described in Formula (I) and their use as therapeutic agent in the attenuation, inhibition, or prevention of cancer cell migration and cancer cell proliferation.

  本发明提供了如公式(I)所述的卤乙基脲化合物，并将其用作治疗剂，用于减轻、抑制或预防癌细胞迁移和癌细胞增殖。
• 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.