methyl 4-(3-phenylureido)benzoate | 53865-58-0

• 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: methyl 4-(3-phenylureido)benzoate
• 英文别名: methyl 4-[(phenylcarbamoyl)amino]benzoate；4-(N'-phenyl-ureido)-benzoic acid methyl ester；4-(N'-Phenyl-ureido)-benzoesaeure-methylester；4-(3-phenylureido)benzoic acid methyl ester；methyl 4-[(anilinocarbonyl)amino]benzoate；methyl 4-(phenylcarbamoylamino)benzoate
• CAS: 53865-58-0
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: FFIFKLISGYQJIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(3-phenylureido)benzoate 在 羟胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 以100%的产率得到N-hydroxy-4-(3-phenylureido)benzamide
  参考文献：
  名称：

  一系列异羟肟酸肉桂酯组蛋白脱乙酰酶抑制剂的构效关系及机理研究

  摘要：

  组蛋白去乙酰化酶 (HDAC) 是一个酶家族，可调节组蛋白和非组蛋白的乙酰化状态。组蛋白去乙酰化酶抑制剂 (HDACis) 已成为治疗多种恶性肿瘤的替代治疗方法。在此，一系列基于尿素的异羟肟酸肉桂酯衍生物被提出作为潜在的抗癌 HDACis。此外，还进行了构效关系 (SAR) 研究以验证接头对化合物生物学特性的影响。所有测试的化合物都显示出对实体和血液人类肿瘤细胞系的显着抗增殖作用。其中，11b对包括 Jurkat 和 Namalwa 在内的血液肿瘤细胞表现出纳摩尔级效力，IC 50值分别为 40 和 200  nM。细胞和分子增殖研究，在化合物11a-d 的存在下显示出显着的细胞生长停滞、细胞凋亡诱导和高达 43 倍的白血病细胞与非致瘤细胞的选择性细胞毒性。此外，化合物11a-d增加了乙酰化 α-微管蛋白的表达水平，这与 HDAC 抑制的表型一致，并间接诱导了 DNA 损伤。对11b进行的体外酶促测定显示出有效的

  DOI：

  10.1016/j.bmc.2021.116085
• 作为产物：
  描述：

  硝基苯 在 iron(III) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、6.08 MPa 条件下， 反应 10.0h， 生成 methyl 4-(3-phenylureido)benzoate
  参考文献：
  名称：

  Polystyrene anchored ruthenium(II) complex catalyzed carbonylation of nitrobenzene and amines for the synthesis of disubstituted ureas

  摘要：

  The catalytically active complex [Ru(PS-imd)(CO)(2)Cl-2] (PS-imd = polystyrene anchored imidazole) was synthesized and characterized using various spectroscopic techniques. The complex is well characterized and highly stable. The catalytic activity of the resulting species was investigated towards the synthesis of diphenyl urea and other disubstituted ureas. The experiments were carried out under high CO pressure, high temperature condition in mild coordinating media. The catalyst was found to produce excellent yields with high product selectivity. Variable yields are obtained depending on the substituent on nitrobenzene and aniline. The effects of co-solvent and co-catalyst were also studied. The catalyst was very stable and could be reused for more than five times without any noticeable loss of its catalytic activity. (c) 2014 Elsevier BY. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.08.017

文献信息

• Synthesis of unsymmetrical biaryl ureas from N-carbamoylimidazoles: kinetics and application
  作者：Tristan Rawling、Andrew M. McDonagh、Bruce Tattam、Michael Murray

  DOI：10.1016/j.tet.2012.05.002

  日期：2012.7

  N-Carbamoylimidazoles dissociate in solution to yield imidazole and an isocyanate that may be reacted with another aryl amine to form an unsymmetrical biaryl urea. This paper investigates the reaction kinetics and the influence of electron withdrawing/donating substituents on the reaction of N-carbamoylimidazoles with aniline. The overall reaction mechanism involves two zwitterionic intermediates,

  N-氨基咪唑在溶液中解离，生成咪唑和异氰酸酯，该异氰酸酯可与另一种芳基胺反应形成不对称的联芳基脲。本文研究了反应动力学以及吸电子/给电子取代基对氮反应的影响-氨基甲酰咪唑与苯胺。整个反应机理涉及两个两性离子中间体，它们在离解过程中以及释放的异氰酸酯与苯胺反应时形成。该反应的限速步骤是来自第二两性离子中间体的碱催化的质子转移。尽管芳基上的吸电子取代基阻碍了解离，但与带有给电子取代基的化合物相比，它们显着提高了反应速率。解离时释放的咪唑催化速率确定步骤，因此解离的N-氨基甲酰咪唑的反应比仅涉及异氰酸酯的反应进行得更快。另外，咪唑消除了对无水反应条件的需要。该ñ制备索拉非尼（一种联芳基脲激酶抑制剂）以高收率和优异的纯度证明了-氨基甲酰咪唑的方法学。
• Diaryl Ureas as CB1 Antagonists
  申请人：Hutchison Alan J.

  公开号：US20090239841A1

  公开（公告）日：2009-09-24

  Compounds of Formula I are provided. In which the variables are as described herein. Such compounds may be used to modulate CB1 activity in vivo or in vitro, and are particularly useful in the treatment of conditions responsive to CB1 modulation in humans, domesticated companion animals and livestock animals, including appetite disorders, obesity and addictive disorders. Pharmaceutical compositions and methods for using them to treat such disorders are provided, as are methods for using such ligands for receptor localization studies and various in vitro assays.

  提供式I的化合物，其中变量如本文所述。这些化合物可用于体内或体外调节CB1活性，并且在治疗对CB1调节敏感的人类、家养伴侣动物和家畜动物的食欲障碍、肥胖和成瘾障碍方面特别有用。提供了用于治疗这些障碍的制药组合物和方法，以及用于受体定位研究和各种体外测定的配体的使用方法。
• Aryl Urea Derivatives for Treating Obesity
  申请人：Bloxham Jason

  公开号：US20080261952A1

  公开（公告）日：2008-10-23

  A method of treating a condition associated with the CB-1 receptor, in particular obesity, by administering an effective amount of an aryl urea CB-1 receptor modulating compound to a subject in need of such treatment.

  通过向需要此类治疗的受试者施用有效量的芳基脲CB-1受体调节化合物来治疗与CB-1受体相关的疾病，尤其是肥胖症的方法。
• Development of Receptor for Advanced Glycation End Products (RAGE) ligands through target directed dynamic combinatorial chemistry: a novel class of possible antagonists
  作者：Anca‐Elena Dascalu、Christophe Furman、Isabelle Landrieu、François‐Xavier Cantrelle、Justine Mortelecque、Gaëlle Grolaux、Philippe Gillery、Frédéric Tessier、Emmanuelle Lipka、Muriel Billamboz、Eric Boulanger、Alina Ghinet

  DOI：10.1002/chem.202303255

  日期：2024.4.5

  Tackling the Receptor for Advanced Glycation End Products (RAGE) inhibition via Dynamic Combinatorial Chemistry (DCC). Leveraging protein recognition, in the presence of a continually self-correcting, evolving dynamic library, we were able to find novel ligands for RAGE. Our biological tests confirmed their superior affinities, as well as potential as antagonists, a fresh perspective for inhibiting

  通过动态组合化学 (DCC) 解决高级糖基化终产物 (RAGE) 受体抑制问题。利用蛋白质识别，在不断自我修正、不断进化的动态库的存在下，我们能够找到 RAGE 的新型配体。我们的生物测试证实了它们卓越的亲和力以及作为拮抗剂的潜力，为抑制这种多方面的炎症相关受体提供了新的视角。
• Identification of novel phenylalanine derivatives bearing a hydroxamic acid moiety as potent quorum sensing inhibitors
  作者：Truong Thanh Tung、Nguyen Quoc Thang、Nguyen Cao Huy、Pham Bao Phuong、Dinh Ngoc Minh、Nguyen Hai Nam、John Nielsen

  DOI：10.1039/d3md00670k

  日期：——

  Phenylalanine derivatives are a well-known small moiety responsible for controlling the virulence factors of several bacteria. Herein, for the first time, we report novel structures of phenylalanine derivatives bearing a hydroxamic acid moiety which were designed, synthesized, and evaluated for use as quorum sensing inhibitors. Biological results reveal that six compounds showed good quorum sensing

  苯丙氨酸衍生物是众所周知的小分子，负责控制多种细菌的毒力因子。在此，我们首次报道了带有异羟肟酸部分的苯丙氨酸衍生物的新结构，该衍生物被设计、合成和评估用作群体感应抑制剂。生物学结果表明，六种化合物表现出良好的群体感应抑制剂特性，IC 50范围为 7.12 ± 2.11 μM–92.34 ± 2.09 μM（ 4NPO ，参考化合物，IC 50 = 29.13 ± 0.88 μM）。此外，与4NPO相比，六种化合物中的三种（ 4a 、 4c 、 4h ）显示出较强的抗生物膜形成和CviR抑制活性。这些生物学数据也得到了计算研究的证实。在该系列化合物中， 4h是未来针对群体感应药物开发最有前景的化合物。我们的结果得出的结论是，基于片段的药物设计是未来发现新型群体感应抑制剂的好方法。