N-(2-acetylphenyl)-N'-(2-methylphenyl)urea | 905535-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-acetylphenyl)-N'-(2-methylphenyl)urea
• 英文别名: 1-(2-acetylphenyl)-3-(2-methylphenyl)urea
• CAS: 905535-25-3
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: HZUUFNNDBPNPHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻氨基苯乙酮 、 邻甲苯异氰酸酯 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以88%的产率得到N-(2-acetylphenyl)-N'-(2-methylphenyl)urea
  参考文献：
  名称：

  Unsymmetrical 1,3-disubstituted urea derivatives as α-chymotrypsin inhibitors

  摘要：

  The objective of this study was to synthesize potent and/or novel inhibitors for alpha-chymotrypsin activity. Eighteen derivatives of N-methylphenyl-N'-(alkyl/aryl) urea (1-18) were synthesized, and their inhibitory effects on alpha-chymotrypsin enzyme were evaluated. Two compounds exhibited potent inhibitory activities. The most potent, N-(2-methylphenyl)-2-oxo-1-pyrrolidinecarboxamide (15) having a methyl group at ortho position was the most active inhibitor with an IC50 value of 8.10 +/- A 0.14 mu M, which was comparable to standard chymostatin (IC50 = 8.24 +/- A 0.11 mu M). A slightly less potent, N-(2-acetylphenyl)-N'-(3-methylphenyl) urea (10), exhibited an IC50 of 13.6 +/- A 0.23 mu M. Compounds 3, 4, 7, 11, and 13 exhibited moderate activities. The results demonstrated that alpha-chymotrypsin inhibition is related to the position of the methyl group and the presence of substituent at the nitrogen of the urea bridge. The inhibitory trend suggests that alpha-chymotrypsin inhibitory activity declines with ortho > meta > para substitution order. In conclusion, our data suggest that the compound 15 may serve as a lead compound for further designing of other potent or novel alpha-chymotrypsin inhibitors.

  DOI：

  10.1007/s00044-014-0930-3