N-(p-bromophenyl)-N'-butylurea | 137351-54-3

• 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: N-(p-bromophenyl)-N'-butylurea
• 英文别名: N-butyl-N'-(4-bromophenyl)urea；1-(4-bromophenyl)-3-butylurea；N-(4-bromo-phenyl)-N'-butyl-urea；N-(4-Brom-phenyl)-N'-butyl-harnstoff
• CAS: 137351-54-3
• 化学式: C₁₁H₁₅BrN₂O
• mdl: MFCD00017798
• 分子量: 271.157
• InChiKey: HZVVVBAMBJDMHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  329.6±34.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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：

  N-(p-bromophenyl)-N'-butylurea 在 盐酸 、 palladium diacetate 、 三乙胺 、 二异丙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 14.0h， 生成 3-butyl-1-{4'-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methyl]-[1,1'-biphenyl]-4-yl}urea
  参考文献：
  名称：

  Design, Biological Evaluation, and Molecular Modeling of Tetrahydroisoquinoline Derivatives: Discovery of A Potent P-Glycoprotein Ligand Overcoming Multidrug Resistance in Cancer Stem Cells

  摘要：

  P-Glycoprotein is a well-known membrane transporter responsible for the efflux of an ample spectrum of anticancer drugs. Its relevance in the management of cancer chemotherapy is increased in view of its high expression in cancer stem cells, a population of cancer cells with strong tumor-promoting ability. In the present study, a series of compounds were synthesized through structure modulation of [4'-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-bipheny1-4-ol] (MC70), modifying the phenolic group of the lead compound. Among them, compound 513 emerged for its activity against the transporter (EC50 = 15 nM) and was capable of restoring doxorubicin antiproliferative activity at nontoxic concentration. Its behavior was rationalized through a molecular modeling study consisting of a well-tempered metadynamics simulation, which allowed one to identify the most favorable binding pose, and of a subsequent molecular dynamics run, which indicated a peculiar effect of the compound on the motion pattern of the transporter.

  DOI：

  10.1021/acs.jmedchem.8b01655
• 作为产物：
  描述：

  N-butyl-N'-phenylurea 在 1,3,5-三溴-1,3,5-噻嗪烷-2,4,6-三酮 作用下， 以 乙腈 为溶剂， 以91%的产率得到N-(p-bromophenyl)-N'-butylurea
  参考文献：
  名称：

  三卤代异氰尿酸对不对称N-苄基和N-苯基脲的高效直接卤化反应

  摘要：

  摘要 在室温下，使用三卤异氰尿酸在乙腈中开发了一种简单有效的方法，用于直接卤化N-苯基脲。该方案被证明对于构建具有不同取代模式的N-苯基脲是有效的。另外，在室温下，在三氟乙酸和乙腈的混合物存在下，将反应性较低的N-苄基脲卤化。 在室温下，使用三卤异氰尿酸在乙腈中开发了一种简单有效的方法，用于直接卤化N-苯基脲。该方案被证明对于构建具有不同取代模式的N-苯基脲是有效的。另外，在室温下，在三氟乙酸和乙腈的混合物存在下，将反应性较低的N-苄基脲卤化。

  DOI：

  10.1055/s-0036-1589149

文献信息

• 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
  申请人：KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY 한국생산기술연구원(319999029382) BRN ▼119-82-01008

  公开号：KR102289502B1

  公开（公告）日：2021-08-13

  본 발명은 유기전기소자의 제1전극과 제2전극 사이에 배치되는 유기박막을 형성하기 위한 유기화합물로서, 상기 유기박막을 형성하기 위한 코어 물질의 말단에 적어도 2개 이상의 아마이드기(amide functional group)를 포함하는 것을 특징으로 한다.

  本发明涉及一种用于形成有机薄膜的有机化合物，其被布置在有机电子器件的第一电极和第二电极之间，其特征在于，在用于形成该有机薄膜的核心物质的末端至少包含2个或更多的酰胺官能团。
• Boehmer, Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 379,383
  作者：Boehmer

  DOI：——

  日期：——
• Danihel, Ivan; Barnikol, Falk; Kristian, Pavol, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 8, p. 1662 - 1670
  作者：Danihel, Ivan、Barnikol, Falk、Kristian, Pavol

  DOI：——

  日期：——
• Efficient Direct Halogenation of Unsymmetrical N-Benzyl- and N-Phenylureas with Trihaloisocyanuric Acids
  作者：Lúcia de Aguiar、Marcio de Mattos、Carlos Sanabria、Bruno Costa、Gil Viana

  DOI：10.1055/s-0036-1589149

  日期：2018.3

  halogenation of N-phenylureas was developed using trihaloisocyanuric acids in acetonitrile at room temperature. This protocol proved to be effective for the construction of N-phenylureas with different patterns of substitution. Additionally, less reactive N-benzylureas were halogenated in the presence of a mixture of trifluoroacetic acid and acetonitrile at room temperature. A simple and efficient methodology

  摘要 在室温下，使用三卤异氰尿酸在乙腈中开发了一种简单有效的方法，用于直接卤化N-苯基脲。该方案被证明对于构建具有不同取代模式的N-苯基脲是有效的。另外，在室温下，在三氟乙酸和乙腈的混合物存在下，将反应性较低的N-苄基脲卤化。 在室温下，使用三卤异氰尿酸在乙腈中开发了一种简单有效的方法，用于直接卤化N-苯基脲。该方案被证明对于构建具有不同取代模式的N-苯基脲是有效的。另外，在室温下，在三氟乙酸和乙腈的混合物存在下，将反应性较低的N-苄基脲卤化。
• Design, Biological Evaluation, and Molecular Modeling of Tetrahydroisoquinoline Derivatives: Discovery of A Potent P-Glycoprotein Ligand Overcoming Multidrug Resistance in Cancer Stem Cells
  作者：Chiara Riganti、Marialessandra Contino、Stefano Guglielmo、Maria G. Perrone、Iris C. Salaroglio、Vladan Milosevic、Roberta Giampietro、Francesco Leonetti、Barbara Rolando、Loretta Lazzarato、Nicola A. Colabufo、Roberta Fruttero

  DOI：10.1021/acs.jmedchem.8b01655

  日期：2019.1.24

  P-Glycoprotein is a well-known membrane transporter responsible for the efflux of an ample spectrum of anticancer drugs. Its relevance in the management of cancer chemotherapy is increased in view of its high expression in cancer stem cells, a population of cancer cells with strong tumor-promoting ability. In the present study, a series of compounds were synthesized through structure modulation of [4'-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-bipheny1-4-ol] (MC70), modifying the phenolic group of the lead compound. Among them, compound 513 emerged for its activity against the transporter (EC50 = 15 nM) and was capable of restoring doxorubicin antiproliferative activity at nontoxic concentration. Its behavior was rationalized through a molecular modeling study consisting of a well-tempered metadynamics simulation, which allowed one to identify the most favorable binding pose, and of a subsequent molecular dynamics run, which indicated a peculiar effect of the compound on the motion pattern of the transporter.