1-(4-Aminophenyl)-3-(3-bromophenyl)urea | 1153283-14-7

• 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-(4-Aminophenyl)-3-(3-bromophenyl)urea
• CAS: 1153283-14-7
• 化学式: C₁₃H₁₂BrN₃O
• mdl: MFCD12414534
• 分子量: 306.162
• InChiKey: QBFMNTWPQBIYMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-1-苯基-1H-吡唑并[3,4-d]嘧啶 、 1-(4-Aminophenyl)-3-(3-bromophenyl)urea 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以66.4%的产率得到1-(3-bromophenyl)-3-(4-((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)phenyl)urea
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative activity of novel pyrazolo[3,4-d]pyrimidine derivatives

  摘要：

  一系列新型吡唑并[3,4-d]嘧啶衍生物被设计、合成并评估其抗增殖活性。

  DOI：

  10.1039/c5md00127g
• 作为产物：
  描述：

  3-溴苯基异氰酸酯 在 tin(II) chloride dihydrate 作用下， 以 二氯甲烷 为溶剂， 生成 1-(4-Aminophenyl)-3-(3-bromophenyl)urea
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative activity of novel pyrazolo[3,4-d]pyrimidine derivatives

  摘要：

  一系列新型吡唑并[3,4-d]嘧啶衍生物被设计、合成并评估其抗增殖活性。

  DOI：

  10.1039/c5md00127g

文献信息

• Discovery of potent thieno[2,3-d]pyrimidine VEGFR-2 inhibitors: Design, synthesis and enzyme inhibitory evaluation supported by molecular dynamics simulations
  作者：Eman Z. Elrazaz、Rabah A.T. Serya、Nasser S.M. Ismail、Amgad Albohy、Dalal A. Abou El Ella、Khaled A.M. Abouzid

  DOI：10.1016/j.bioorg.2021.105019

  日期：2021.8

  angiogenesis and cancer progression. In this study, we are reporting the design, synthesis and biological evaluation of a series of 4-substituted thieno[2,3-d]pyrimidine derivatives as VEGFR-2 inhibitors. The design of these compounds was based on interactions extracted from crystal structure of potent pyrrolo[3,2-d]pyrimidine inhibitor VIII with VEGFR-2 (PDB: 3VHE). In addition to these interactions, the

  血管内皮生长因子受体 (VEGFR) 是众所周知的控制血管生成和癌症进展的靶标之一。在这项研究中，我们报告了一系列 4-取代的噻吩并[2,3- d ]嘧啶衍生物作为 VEGFR-2 抑制剂的设计、合成和生物学评价。这些化合物的设计基于从有效吡咯并[3,2- d ]嘧啶抑制剂VIII与 VEGFR-2 (PDB: 3VHE) 的晶体结构中提取的相互作用。除了这些相互作用之外，新化合物还被设计为与溶剂可及区域中的残基相互作用，例如 Asn923。因此，合成噻吩并嘧啶目标化合物并进行VEGFR-2酶抑制测定。几种目标化合物（7d-f、8b-c、8e-g和15c ) 表现出对 VEGFR-2 的有效抑制活性，IC 50值在低纳摩尔范围内。化合物8b和8e显示出异常有效的抑制活性，IC 50 分别为5和3.9  nM。还进行了分子对接分析和分子动力学模拟，以进一步研究这些发现。
• Structure-based design and synthesis of novel pseudosaccharine derivatives as antiproliferative agents and kinase inhibitors
  作者：Mohamed S.A. Elsayed、Moustafa E. El-Araby、Rabah A.T. Serya、Ahmed H. El-Khatib、Michael W. Linscheid、Khaled A.M. Abouzid

  DOI：10.1016/j.ejmech.2012.09.039

  日期：2013.3

  This study is concerned with the implementation of structure-based techniques for the design of new heterocyclic compounds based on pseudosaccharine scaffold with protein kinase inhibition activity. This nucleus was exploited based on the well-known quinazoline core and its interactions with several protein kinases. Two series of compounds employing this new scaffold were synthesized and evaluated at enzymatic and cellular levels. Compound 9b displayed broad spectrum antiproliferative activity on NCI 60-cell lines panel with mean GI(50) of 5.4 mu M. Investigation of the molecular mechanism showed probable inhibitory activity against Src kinase. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of di-aryl urea derivatives as c-Kit inhibitors
  作者：Séverine Ravez、Stéphane Arsenlis、Amélie Barczyk、Anthony Dupont、Raphaël Frédérick、Stéphanie Hesse、Gilbert Kirsch、Patrick Depreux、Laurence Goossens

  DOI：10.1016/j.bmc.2015.10.035

  日期：2015.11

  Inhibition of receptor tyrosine kinases (RTKs) continued to be a successful approach for the treatment of many types of human cancers and many potent small molecules kinase inhibitors have been discovered the last decade. In the present study, we describe the synthesis of thienopyrimidine derivatives and their pharmacological evaluation against nine kinases (EGFR, PDGFR-ss, c-Kit, c-Met, Src, Raf, VEGFR-1, -2 and -3). Most of the synthesized compounds showed from moderate to potent activities against c-Kit with IC50 values in the nanomolar range. Among them, 4-anilino(urea) thienopyrimidine analogs showed selectivity and potent c-Kit inhibition with IC50 values less than 6 nM. Docking simulation was performed for the most promising compound 9 into the c-Kit active site to determine the potential binding mode. This study reveal that the 4-anilino(urea) thienopyrimidine is an interesting scaffold to design novel potent and selective c-Kit inhibitors which may make promising candidates for cancers where c-Kit receptors are overexpressed. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro antiproliferative activity of novel pyrazolo[3,4-d]pyrimidine derivatives
  作者：Nermin S. Abdou、Rabah A. T. Serya、Ahmed Esmat、Mai F. Tolba、Nasser S. M. Ismail、Khaled A. M. Abouzid

  DOI：10.1039/c5md00127g

  日期：——

  A novel series of pyrazolo[3,4-d]pyrimidine derivatives were designed, synthesized and evaluated for their antiproliferative activity.

  一系列新型吡唑并[3,4-d]嘧啶衍生物被设计、合成并评估其抗增殖活性。