1-(5-甲基-2-苯基吡唑-3-基)-3-苯基脲 | 337975-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(5-甲基-2-苯基吡唑-3-基)-3-苯基脲
• 英文名称: 1-(5-methyl-2-phenyl-2H-pyrazol-3-yl)-3-phenylurea
• 英文别名: CID 736191；CID-736191；VU0032230；N-(5-methyl-2-phenyl-2H-pyrazol-3-yl)-N'-phenyl-urea；N-(5-Methyl-2-phenyl-2H-pyrazol-3-yl)-N'-phenyl-harnstoff；1-(5-Methyl-2-phenyl-2H-pyrazol-3-yl)-3-phenyl-urea；1-(5-methyl-2-phenylpyrazol-3-yl)-3-phenylurea
• CAS: 337975-77-6
• 化学式: C₁₇H₁₆N₄O
• 分子量: 292.34
• InChiKey: KJTYQAYFNWYLFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-甲基-2-苯基吡唑-3-基)-3-苯基脲 在 吡啶 、 双氧水 作用下， 以 甲苯 为溶剂， 反应 48.5h， 生成
  参考文献：
  名称：

  Phosphorylation of Arylureas and Arylcarbamates: A New Prospect

  摘要：

  在适当位置具有电子捐赠取代基的 N,N′-芳基脲与溴化磷（III）发生反应，形成新的杂环系统 2,4,1-苯并二氮杂环膦-3-酮。N-（5-吡唑基）、N′-芳脲类和 N,O-二芳基氨基甲酸酯也会发生类似的杂环化反应，生成 1H-吡唑并[4,3-c][1,5,2]二氮杂萘-3-酮和 2,4,1-苯并噁唑膦-3-酮环系统。

  DOI：

  10.1055/s-2005-916029
• 作为产物：
  描述：

  5-氨基-3-甲基-1-苯基吡唑 、 异氰酸苯酯 以 乙腈 为溶剂， 以84%的产率得到1-(5-甲基-2-苯基吡唑-3-基)-3-苯基脲
  参考文献：
  名称：

  Synthesis of pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-ones

  摘要：

  A small library of hitherto unprepared pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-ones was synthesized on a preparative scale. The synthesis starts with a substituted 5-aminopyrazole that reacts with an isocyanate to give the corresponding urea. The latter undergoes a chlorotrimethylsilane-promoted [5+1] cyclocondensation with an aldehyde yielding the title pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-one. Both synthetic steps are high-yielding (74-94%). The intermediates and the target compounds were isolated by simple crystallization. Ketones with the exception of isatin do not react with the open-chain urea intermediates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.131

文献信息

• UREA DERIVATIVES AS ABL MODULATORS
  申请人：Grotzfeld Robert M.

  公开号：US20100173917A1

  公开（公告）日：2010-07-08

  The invention provides methods and compositions for treating conditions mediated by Bcr-Abl. The invention also provides methods of using the compounds and/or compositions in the treatment of a variety of diseases and unwanted conditions in subjects.

  本发明提供了治疗由Bcr-Abl介导的疾病的方法和组合物。本发明还提供了使用这些化合物和/或组合物治疗受试者的各种疾病和不良情况的方法。
• Pyrazole Urea-Based Inhibitors of p38 MAP Kinase:  From Lead Compound to Clinical Candidate
  作者：John Regan、Steffen Breitfelder、Pier Cirillo、Thomas Gilmore、Anne G. Graham、Eugene Hickey、Bernhard Klaus、Jeffrey Madwed、Monica Moriak、Neil Moss、Chris Pargellis、Sue Pav、Alfred Proto、Alan Swinamer、Liang Tong、Carol Torcellini

  DOI：10.1021/jm020057r

  日期：2002.7.1

  We report on a series of N-pyrazole, N'-aryl ureas and their mode of binding to p38 mitogen activated protein kinase. Importantly, a key binding domain that is distinct from the adenosine 5'-triphoshate (ATP) binding site is exposed when the conserved activation loop, consisting in part of Asp168-Phe169-Gly170, adopts a conformation permitting lipophilic and hydrogen bonding interactions between this class of inhibitors and the protein. We describe the correlation of the structure-activity relationships and crystallographic structures of these inhibitors with p38. In addition, we incorporated another binding pharmacophore that forms a hydrogen bond at the ATP binding site. This modification affords significant improvements in binding, cellular, and in vivo potencies resulting in the selection of 45 (BIRB 796) as a clinical candidate for the treatment of inflammatory diseases.
• Michaelis; Schaefer, Justus Liebigs Annalen der Chemie, 1913, vol. 397, p. 144
  作者：Michaelis、Schaefer

  DOI：——

  日期：——
• US7750160B2
  申请人：——

  公开号：US7750160B2

  公开（公告）日：2010-07-06
• Synthesis of pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-ones
  作者：Sergey V. Ryabukhin、Dmitry S. Granat、Andrey S. Plaskon、Alexander Shivanyuk、Oleg Lukin

  DOI：10.1016/j.tetlet.2014.01.131

  日期：2014.3

  A small library of hitherto unprepared pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-ones was synthesized on a preparative scale. The synthesis starts with a substituted 5-aminopyrazole that reacts with an isocyanate to give the corresponding urea. The latter undergoes a chlorotrimethylsilane-promoted [5+1] cyclocondensation with an aldehyde yielding the title pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-one. Both synthetic steps are high-yielding (74-94%). The intermediates and the target compounds were isolated by simple crystallization. Ketones with the exception of isatin do not react with the open-chain urea intermediates. (C) 2014 Elsevier Ltd. All rights reserved.