3-methyl-2-thioxo-2,3-dihydro-imidazole-1-carboxylic acid benzyl ester | 100142-91-4

• 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: 3-methyl-2-thioxo-2,3-dihydro-imidazole-1-carboxylic acid benzyl ester
• 英文别名: 3-Methyl-2-thioxo-2,3-dihydro-imidazol-1-carbonsaeure-benzylester；Benzyl 3-methyl-2-sulfanylideneimidazole-1-carboxylate
• CAS: 100142-91-4
• 化学式: C₁₂H₁₂N₂O₂S
• 分子量: 248.305
• InChiKey: XPRRHEAYRYKMTF-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C(Solvent: Benzene ; Ligroine)
• 沸点：
  354.0±35.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-2-thioxo-2,3-dihydro-imidazole-1-carboxylic acid benzyl ester 反应 730.5h， 生成 2-(benzylthio)-1-methyl-1H-imidazole
  参考文献：
  名称：

  Antithyroid Drug Carbimazole and Its Analogues: Synthesis and Inhibition of Peroxidase-Catalyzed Iodination of l-Tyrosine

  摘要：

  Synthesis and biological activity of the antithyroid drug carbimazole (CBZ) and its analogues are described. The introduction of an ethoxycarbonyl group in methimazole and its selenium analogue not only prevents the oxidation to the corresponding disulfide and diselenide but also reduces the zwitterionic character. A structure-activity correlation in a series of CBZ analogues suggests that the presence of a methyl substituent in CBZ and related compounds is important for their antithyroid activity.

  DOI：

  10.1021/jm800894m
• 作为产物：
  描述：

  N-甲基咪唑 、 氯甲酸苄酯 在 正丁基锂 、 sulfur 作用下， 生成 3-methyl-2-thioxo-2,3-dihydro-imidazole-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Antithyroid Drug Carbimazole and Its Analogues: Synthesis and Inhibition of Peroxidase-Catalyzed Iodination of l-Tyrosine

  摘要：

  Synthesis and biological activity of the antithyroid drug carbimazole (CBZ) and its analogues are described. The introduction of an ethoxycarbonyl group in methimazole and its selenium analogue not only prevents the oxidation to the corresponding disulfide and diselenide but also reduces the zwitterionic character. A structure-activity correlation in a series of CBZ analogues suggests that the presence of a methyl substituent in CBZ and related compounds is important for their antithyroid activity.

  DOI：

  10.1021/jm800894m

文献信息

• 230. 2-Mercaptoglyoxalines. Part X. The acylation of 2-mercaptoglyoxalines
  作者：Alexander Lawson、H. V. Morley

  DOI：10.1039/jr9560001103

  日期：——
• Antithyroid Drug Carbimazole and Its Analogues: Synthesis and Inhibition of Peroxidase-Catalyzed Iodination of <scp>l</scp>-Tyrosine
  作者：Debasis Das、Gouriprasanna Roy、Govindasamy Mugesh

  DOI：10.1021/jm800894m

  日期：2008.11.27

  Synthesis and biological activity of the antithyroid drug carbimazole (CBZ) and its analogues are described. The introduction of an ethoxycarbonyl group in methimazole and its selenium analogue not only prevents the oxidation to the corresponding disulfide and diselenide but also reduces the zwitterionic character. A structure-activity correlation in a series of CBZ analogues suggests that the presence of a methyl substituent in CBZ and related compounds is important for their antithyroid activity.