N-(4-nitrophenyl)-N'-(1-phenylethyl)urea | 154059-66-2

• 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-(4-nitrophenyl)-N'-(1-phenylethyl)urea
• 英文别名: 1-(4-Nitrophenyl)-3-(1-phenylethyl)urea
• CAS: 154059-66-2
• 化学式: C₁₅H₁₅N₃O₃
• 分子量: 285.302
• InChiKey: YUYLCSCQSJELQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenyl)-N'-(1-phenylethyl)urea 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 生成 1-(4-aminophenyl)-3-(1-phenylethyl) urea
  参考文献：
  名称：

  [EN] UREA SUBSTITUTED SULPHONAMIDE DERIVATIVES
  [FR] DERIVES DE SULFONAMIDE SUBSTITUES PAR UREE

  摘要：

  本发明涉及含有脲基的磺胺类衍生物。该发明还涉及将这些衍生物用作胶原受体整合素的抑制剂，特别是α2β1整合素抑制剂，例如在涉及表达胶原受体的细胞和血小板的疾病和医疗状况中使用，其用作药物，例如用于治疗血栓形成、炎症、癌症和血管疾病，含有它们的药物组合物以及制备它们的方法。这些磺胺类衍生物具有一般式(I)或(I')。

  公开号：

  WO2010146236A1
• 作为产物：
  描述：

  4-硝基苯胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(4-nitrophenyl)-N'-(1-phenylethyl)urea
  参考文献：
  名称：

  Structure–Activity Relationship Studies of Pyrazolo[3,4-d]pyrimidine Derivatives Leading to the Discovery of a Novel Multikinase Inhibitor That Potently Inhibits FLT3 and VEGFR2 and Evaluation of Its Activity against Acute Myeloid Leukemia in Vitro and in Vivo

  摘要：

  We describe the structural optimization of a hit compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl)-3-(3-methoxyphenyl)urea (1), which exhibits inhibitory activity but low potency against FLT3 and VEGFR2. A series of pyrazolo [3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis using cell- and transgenic-zebrafish-based assays led to the discovery of a number of compounds that exhibited both high potency against FLT3-driven human acute myeloid leukemia (AML) MV4-11 cells and a considerable antiangiogenic effect in transgenic-zebrafish-based assays. The compound 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (33), which exhibited the highest activity in preliminary in vivo anti-AML assays, was chosen for further anti AML studies. The results demonstrated that compound 33 is a multikinase inhibitor that potently inhibits FLT3 and VEGFR2. In an MV4-11 xenograft mouse model, a once daily dose of compound 33 at 10 mg/kg for 18 days led to complete tumor regression without obvious toxicity. Western blot and immunohistochemical analyses were performed to determine the mechanism of action of compound 33.

  DOI：

  10.1021/jm301537p

文献信息

• Substituted Urea Derivatives: A Potent Class of Antidepressant Agents
  作者：Shahnaz Perveen、Sana Mustafa、Muhammad A. Khan、Ahsana Dar、Khalid M. Khan、Wolfgang Voelter

  DOI：10.2174/157340612800786615

  日期：2012.5.1

  A series of fourteen (14) N-nitrophenyl-N'-(alkyl/aryl)urea and symmetrical 1,3-disubstituted urea derivatives were synthesized and evaluated for their antidepressant activity in mice. Among them, N-(4-nitrophenyl)-N'-(1'-phenylethyl)urea (1), demonstrated profound antidepressant property as reflected by significant reduction in the immobility time (89.83%), whereas compounds 2-6 showed activity values

  合成了一系列十四（14）种N-硝基苯基-N'-（烷基/芳基）脲和对称的1,3-二取代的脲衍生物，并评估了它们在小鼠中的抗抑郁活性。其中，N-（4-硝基苯基）-N'-（1'-苯乙基）脲（1）具有很强的抗抑郁作用，其固定时间显着减少（89.83％），而化合物2-6具有活性值在36％至59％之间，也比标准苯乙嗪大。化合物7-9在将小鼠的不动周期减少26.20至31.01％方面不太有效。抗抑郁活性的这种变化幅度似乎与硝基相对于母体分子1、2和8的位置有关。硝基处在对位的化合物1被证明是最有效的抗抑郁剂。但是，活动减少了
• UREA SUBSTITUTED SULPHONAMIDE DERIVATIVES
  申请人：Koivunen Jarkko Tapani

  公开号：US20120196884A1

  公开（公告）日：2012-08-02

  The present invention relates to sulphonamide derivatives, whith a urea moiety. The invention also relates to the use of the derivatives as inhibitors of collagen receptor integrins, especially α2β1 integrin inhibitors e.g. in connection with diseases and medical conditions that involve the action of cells and platelets expressing collagen receptors, their use as a medicament, e.g. for the treatment of thrombosis, inflammation, cancer and vascular diseases, pharmaceutical compositions containing them and a process for preparing them. The sulphonamide derivatives have the general formula (I) or (I′).

  本发明涉及含有尿素基团的磺酰胺衍生物。本发明还涉及将这些衍生物用作胶原受体整合素的抑制剂，特别是α2β1整合素抑制剂，例如在涉及表达胶原受体的细胞和血小板的疾病和医疗状况中，将其用作药物，例如用于治疗血栓形成、炎症、癌症和血管疾病，包含它们的制药组合物以及制备它们的过程。磺酰胺衍生物具有通式（I）或（I′）。
• Antiproliferative effects of novel urea derivatives against human prostate and lung cancer cells; and their inhibition of β-glucuronidase activity
  作者：Shahnaz Perveen、Sana Mustafa、Kehkashan Qamar、Ahsana Dar、Khalid M. Khan、Muhammad Iqbal Choudhary、Ajmal Khan、Wolfgang Voelter

  DOI：10.1007/s00044-013-0702-5

  日期：2014.3

  Twenty-one novel urea derivatives were synthesized and their structures characterized by mass, NMR, IR, and UV spectroscopy. These compounds were evaluated for their antiproliferative profile against human PC-3 (prostate) and NCI-H460 (lung) cancer cell lines. Among them, compound 21 N-(3-nitrophenyl)-N'-(1-phenylethyl)urea was found to be active against both PC-3 (IC50 +/- A SEM: 20.13 +/- A 0.91 mu M) and NCI-H460 (GI(50): 22 +/- A 2.6 mu M) cell lines; hence has the potential to be further studied as anticancer agent. These compounds were also investigated for their ability to inhibit urease, beta-glucuronidase, and phosphodiesterase enzymes. N-(2,6-Dimethylphenyl)-N'-(4'-nitrophenyl)urea (1) demonstrated 90 % inhibition of beta-glucuronidase enzyme (IC50 +/- A SEM: 3.38 +/- A 0.043 mu M).
• Perveen, Shahnaz; Mustafa, Sana; Khan, Khalid Mohammed, Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 6, p. 1603 - 1611
  作者：Perveen, Shahnaz、Mustafa, Sana、Khan, Khalid Mohammed、Choudhary, Muhammad Iqbal

  DOI：——

  日期：——
• [EN] UREA SUBSTITUTED SULPHONAMIDE DERIVATIVES<br/>[FR] DERIVES DE SULFONAMIDE SUBSTITUES PAR UREE
  申请人：BIOTIE THERAPIES CORP

  公开号：WO2010146236A1

  公开（公告）日：2010-12-23

  The present invention relates to sulphonamide derivatives, whith a urea moiety. The invention also relates to the use of the derivatives as inhibitors of collagen receptor integrins, especially α2β1 integrin inhibitors e.g. in connection with diseases and medical conditions that involve the action of cells and platelets expressing collagen receptors, their use as a medicament, e.g. for the treatment of thrombosis, inflammation, cancer and vascular diseases, pharmaceutical compositions containing them and a process for preparing them. The sulphonamide derivatives have the general formula (I) or (I').

  本发明涉及含有脲基的磺胺类衍生物。该发明还涉及将这些衍生物用作胶原受体整合素的抑制剂，特别是α2β1整合素抑制剂，例如在涉及表达胶原受体的细胞和血小板的疾病和医疗状况中使用，其用作药物，例如用于治疗血栓形成、炎症、癌症和血管疾病，含有它们的药物组合物以及制备它们的方法。这些磺胺类衍生物具有一般式(I)或(I')。