N-(2-methylphenyl)-N′-(4-pyridinyl)urea | 13289-27-5

• 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-(2-methylphenyl)-N′-(4-pyridinyl)urea
• 英文别名: 1-pyridin-4-yl-3-o-tolyl-urea；N-(2-Methyl-phenyl)-N'-(4-pyridyl)-harnstoff；1-(2-Methylphenyl)-3-pyridin-4-ylurea
• CAS: 13289-27-5
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: LFNYGLROLWQWSP-UHFFFAOYSA-N

物化性质

• 熔点：
  >210 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  292.1±23.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氨基吡啶 、 邻甲苯异氰酸酯 以 四氢呋喃 为溶剂， 以78%的产率得到N-(2-methylphenyl)-N′-(4-pyridinyl)urea
  参考文献：
  名称：

  N-Phenyl-N'-pyridinylureas as anticonvulsant agents

  摘要：

  A series of N-phenyl-N'-pyridinylureas was examined for anticonvulsant activity. Extensive structure/activity investigations revealed optimal activity in the N-(2,6-disubstituted-phenyl)-N'-(4-pyridinyl)urea series, with 37 exhibiting the best overall anticonvulsant profile. Compound 37 was effective against seizures induced by maximal electroshock but did not protect mice from clonic seizures produced by the convulsant pentylenetetrazol. The overall pharmacological profile suggests that 37 would be of therapeutic use in the treatment of generalized tonic-clonic and partial seizures. Compound 37 was selected for Phase 1 clinical trials.

  DOI：

  10.1021/jm00164a061

文献信息

• Phosgene-free synthesis of N-aryl-N'-4-pyridinylureas via selenium-catalyzed oxidative carbonylation of 4-aminopyridine with aromatic amines
  作者：Xiaopeng Zhang、Zhengwei Li、Yan Wang、Shuxiang Dong、Xueli Niu、Guisheng Zhang

  DOI：10.3998/ark.5550190.p009.683

  日期：——

  atom economy has been developed for the synthesis of N-aryl-N′-(4-pyridinyl)ureas. With cheap selenium as the catalyst, carbon monoxide (instead of phosgene) as the carbonyl reagent, N-aryl-N′-(4-pyridinyl)ureas can be obtained in a one-pot manner mostly in moderate to good yields via oxidative cross-carbonylation of 4-aminopyridine with a variety of aromatic amines in the presence of oxygen under atmospheric

  已开发出一种简便、无光气且具有高原子经济性的方法来合成 N-芳基-N'-(4-吡啶基)脲。以廉价的硒为催化剂，以一氧化碳（而不是光气）为羰基试剂，可以通过氧化交叉以一锅法获得N-芳基-N'-（4-吡啶基）脲，大部分收率中等至良好- 4-氨基吡啶与多种芳香胺在氧气存在下在大气压下羰基化。还提出了合成N-芳基-N'-(4-吡啶基)脲的机理。
• Stanovnik, B.; Tisler, M.; Golob, V., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 733 - 736
  作者：Stanovnik, B.、Tisler, M.、Golob, V.、Hvala, I.、Nikolic, O.

  DOI：——

  日期：——
• STANOVNIK B.; TISLER M.; GOLOB V.; HVALA I.; NIKOLIC O., J. HETEROCYCL. CHEM., 1980, 17, NO 4, 733-736
  作者：STANOVNIK B.、 TISLER M.、 GOLOB V.、 HVALA I.、 NIKOLIC O.

  DOI：——

  日期：——
• N-Phenyl-N'-pyridinylureas as anticonvulsant agents
  作者：Michael R. Pavia、Sandra J. Lobbestael、Charles P. Taylor、Fred M. Hershenson、David L. Miskell

  DOI：10.1021/jm00164a061

  日期：1990.2

  A series of N-phenyl-N'-pyridinylureas was examined for anticonvulsant activity. Extensive structure/activity investigations revealed optimal activity in the N-(2,6-disubstituted-phenyl)-N'-(4-pyridinyl)urea series, with 37 exhibiting the best overall anticonvulsant profile. Compound 37 was effective against seizures induced by maximal electroshock but did not protect mice from clonic seizures produced by the convulsant pentylenetetrazol. The overall pharmacological profile suggests that 37 would be of therapeutic use in the treatment of generalized tonic-clonic and partial seizures. Compound 37 was selected for Phase 1 clinical trials.