1-(3-fluorophenyl)-3-(4-nitrophenyl)urea | 13252-24-9

• 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-(3-fluorophenyl)-3-(4-nitrophenyl)urea
• 英文别名: 1-(3-Fluorophenyl)-3-(4-nitrophenyl)urea
• CAS: 13252-24-9
• 化学式: C₁₃H₁₀FN₃O₃
• 分子量: 275.239
• InChiKey: PKEJLUOQJUBFNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  334.1±27.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 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：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-fluorophenyl)-3-(4-nitrophenyl)urea 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 N-(4-aminophenyl)-N′-(3-fluorophenyl)urea
  参考文献：
  名称：

  苯基和二芳基脲与噻唑并 [5,4-d] 嘧啶支架作为血管生成抑制剂：设计、合成和生物学评价

  摘要：

  血管生成对肿瘤生长至关重要，抑制血管生成已被视为癌症治疗的一种有前途的方法。血管内皮生长因子受体-2 (VEGFR-2) 是血管生成的重要因素。在这项工作中，合理设计和合成了一系列抑制血管生成的新型噻唑并[5,4-d]嘧啶衍生物。在体外研究了它们对人脐静脉内皮细胞 (HUVEC) 的抑制活性。1-(4-氟苯基)-3-{4-[(5-甲基-2-苯基[1,3]噻唑并[5,4-d]嘧啶-7-基)氨基]苯基}脲(19b)和1-(3-氟苯基)-3-{4-[(5-methyl-2-phenyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl)amino]phenyl}urea (19g)对 HUVEC 增殖最有效的抑制作用（IC50 分别为 12.8 和 5.3 μm）。化合物19g可抑制人脐静脉内皮细胞的迁移。这些结果支持进一步研究这些化合物作为有效的抗癌剂。

  DOI：

  10.1002/cbdv.201800493
• 作为产物：
  描述：

  4-硝基苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(3-fluorophenyl)-3-(4-nitrophenyl)urea
  参考文献：
  名称：

  Design, synthesis and antitumor activity of 4-aminoquinazoline derivatives targeting VEGFR-2 tyrosine kinase

  摘要：

  We report herein the design and synthesis of novel 4-aminoquinazoline derivatives based on the inhibitors of VEGFR-2 tyrosine kinases. The VEGFR-2 inhibitory activities of these newly synthesized compounds were also evaluated and compared with that of ZD6474. We found that most of target compounds had good inhibitory potency. In particular, compounds 1h, 1n and 1o were found to be 6, 2 and 2-fold more potent than the positive control ZD6474. The leading compound 1h also showed an in vivo activity against HepG2 human tumor xenograft model in BALB/c-nu mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.061

文献信息

• Design, synthesis and molecular modeling study of certain VEGFR-2 inhibitors based on thienopyrimidne scaffold as cancer targeting agents
  作者：Amna Ghith、Khairia M. Youssef、Nasser S.M. Ismail、Khaled A.M. Abouzid

  DOI：10.1016/j.bioorg.2018.10.008

  日期：2019.3

  compound 10a. Flow cytometric analysis on both MCV-7 and PC-3 cancer cells revealed that it induced cell-cycle arrest in the G0-G1phase and reinforced apoptosis via activation of caspase-3. Furthermore, molecular modeling studies have been carried out to gain further understanding of the binding mode in the active site of VEGFR-2 enzyme and predict pharmacokinetic properties of all the synthesized inhibitors

  设计，合成和评价了不同系列的新型噻吩并[2，3- d ]嘧啶衍生物（9a-d，10a-f，l，m和15a-m）在体外抑制VEGFR-2酶的能力。而且，通过NCI对60种不同的人类癌细胞系进行了测试，以测试最终化合物的细胞毒性。VEGFR-2酶的抑制结果表明，化合物10d，15d和15 g是活性最高的抑制剂，IC 50值分别为2.5、5.48和2.27 µM，而化合物10a显着显示出最高的细胞生长抑制率，平均生长抑制率（GI）为31.57％。它对几种NCI细胞系表现出广谱的抗增殖活性，特别是对人乳腺癌（T7-47D）和肾癌（A498）细胞系分别具有85.5％和77.65％的抑制作用。为了研究该活性的机制，对化合物10a进行了进一步的生物学研究，例如流式细胞术细胞周期与caspase-3比色测定。对MCV-7和PC-3癌细胞的流式细胞仪分析表明，它诱导了G0-G1期的细胞周期停滞，并通过激活c
• Design, synthesis and evaluation of acridine derivatives as multi-target Src and MEK kinase inhibitors for anti-tumor treatment
  作者：Zhishan Cui、Xi Li、Lulu Li、Bin Zhang、Chunmei Gao、Yuzong Chen、Chunyan Tan、Hongxia Liu、Weiyi Xie、Ti Yang、Yuyang Jiang

  DOI：10.1016/j.bmc.2015.12.011

  日期：2016.1

  Clinical studies have shown enhanced anticancer effects of combined inhibition of Src and MEK kinases. Development of multi-target drugs against Src and MEK is of potential therapeutic advantage against cancers. As a follow-up of our previous studies, and by using molecular docking method, we designed and synthesized a new series of 9-anilinoacridines containing phenyl-urea moieties as potential novel dual Src and MEK inhibitors. The anti-proliferative assays against K562 and HepG-2 tumor cells showed that most of the derivatives displayed good cytotoxicity in vitro. In particular, kinase inhibition assays showed that compound 8m inhibited Src (59.67%) and MEK (43.23%) at 10 mu M, and displayed moderate inhibitory activity against ERK and AKT, the downstream effectors of both Src and MEK. Moreover, compound 8m was found to induce K562 cells apoptosis. Structure-activity relationships of these derivatives were analyzed. Our study suggested that acridine scaffold, particularly compound 8m, is of potential interest for developing novel multi-target Src and MEK kinase inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.
• Phenyl and Diaryl Ureas with Thiazolo[5,4‐ <i>d</i> ]pyrimidine Scaffold as Angiogenesis Inhibitors: Design, Synthesis and Biological Evaluation
  作者：Wen‐Jun Xue、Ya‐Hui Deng、Zhong‐Hui Yan、Ji‐Ping Liu、Yu Liu、Li‐Ping Sun

  DOI：10.1002/cbdv.201800493

  日期：2019.4

  receptor‐2 (VEGFR‐2) is an important factor in angiogenesis. In this work, a novel series of thiazolo[5,4‐d]pyrimidine derivatives inhibiting angiogenesis were rationally designed and synthesized. Their inhibitory activities against human umbilical vein endothelial cells (HUVEC) were investigated in vitro. 1‐(4‐Fluorophenyl)‐3‐4‐[(5‐methyl‐2‐phenyl[1,3]thiazolo[5,4‐d]pyrimidin‐7‐yl)amino]phenyl}urea (19b)

  血管生成对肿瘤生长至关重要，抑制血管生成已被视为癌症治疗的一种有前途的方法。血管内皮生长因子受体-2 (VEGFR-2) 是血管生成的重要因素。在这项工作中，合理设计和合成了一系列抑制血管生成的新型噻唑并[5,4-d]嘧啶衍生物。在体外研究了它们对人脐静脉内皮细胞 (HUVEC) 的抑制活性。1-(4-氟苯基)-3-4-[(5-甲基-2-苯基[1,3]噻唑并[5,4-d]嘧啶-7-基)氨基]苯基}脲(19b)和1-(3-氟苯基)-3-4-[(5-methyl-2-phenyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl)amino]phenyl}urea (19g)对 HUVEC 增殖最有效的抑制作用（IC50 分别为 12.8 和 5.3 μm）。化合物19g可抑制人脐静脉内皮细胞的迁移。这些结果支持进一步研究这些化合物作为有效的抗癌剂。
• Design, synthesis and antitumor activity of 4-aminoquinazoline derivatives targeting VEGFR-2 tyrosine kinase
  作者：Bing Yu、Li-da Tang、Yi-liang Li、Shu-hui Song、Xiao-liang Ji、Mu-sen Lin、Chun-Fu Wu

  DOI：10.1016/j.bmcl.2011.11.061

  日期：2012.1

  We report herein the design and synthesis of novel 4-aminoquinazoline derivatives based on the inhibitors of VEGFR-2 tyrosine kinases. The VEGFR-2 inhibitory activities of these newly synthesized compounds were also evaluated and compared with that of ZD6474. We found that most of target compounds had good inhibitory potency. In particular, compounds 1h, 1n and 1o were found to be 6, 2 and 2-fold more potent than the positive control ZD6474. The leading compound 1h also showed an in vivo activity against HepG2 human tumor xenograft model in BALB/c-nu mice. (C) 2011 Elsevier Ltd. All rights reserved.