5-hydroxymethyl-2-methylthio-1-phenylaminoimidazole | 676566-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-hydroxymethyl-2-methylthio-1-phenylaminoimidazole
• 英文别名: (3-anilino-2-methylsulfanylimidazol-4-yl)methanol
• CAS: 676566-30-6
• 化学式: C₁₁H₁₃N₃OS
• 分子量: 235.31
• InChiKey: PACSNYORKXIFDU-UHFFFAOYSA-N

物化性质

• 沸点：
  455.3±37.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.08
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-hydroxymethyl-2-methylthio-1-phenylaminoimidazole 在 manganese(IV) oxide 作用下， 以 乙腈 为溶剂， 反应 9.0h， 以85%的产率得到2-methylthio-1-phenylaminoimidazole-5-carboxaldehyde
  参考文献：
  名称：

  Synthesis and calcium antagonist activity of 1,4-dihydropyridines containing phenylaminoimidazolyl substituents

  摘要：

  Alkyl ester analogues of nifedipine, in which the ortho-nitrophenyl group at position 4 is replaced by 2-methylthio-1-phenylamino-5-imidazolyl substituent, were synthesized and evaluated as calcium-channel antagonists using the high K(+) contraction of guinea-pig ileal longitudinal smooth muscle. The results for the symmetrical esters showed that in the series of alkyl esters increasing the length of methylene chain in C-3 and C-5 ester substituents for more than two methylene units decreases activity. In the phenylalkyl ester series increasing the length of methylene chain also decreases activity. The results demonstrate that most of the compounds had similar activity to the reference drug nifedipine. In addition, two compounds, 5b and 5f were more active than the nifedipine.

  DOI：

  10.1016/s0014-827x(03)00159-9
• 作为产物：
  描述：

  5-hydroxymethyl-2-mercapto-1-phenylaminoimidazole 、 碘甲烷 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以67%的产率得到5-hydroxymethyl-2-methylthio-1-phenylaminoimidazole
  参考文献：
  名称：

  Synthesis and calcium antagonist activity of 1,4-dihydropyridines containing phenylaminoimidazolyl substituents

  摘要：

  Alkyl ester analogues of nifedipine, in which the ortho-nitrophenyl group at position 4 is replaced by 2-methylthio-1-phenylamino-5-imidazolyl substituent, were synthesized and evaluated as calcium-channel antagonists using the high K(+) contraction of guinea-pig ileal longitudinal smooth muscle. The results for the symmetrical esters showed that in the series of alkyl esters increasing the length of methylene chain in C-3 and C-5 ester substituents for more than two methylene units decreases activity. In the phenylalkyl ester series increasing the length of methylene chain also decreases activity. The results demonstrate that most of the compounds had similar activity to the reference drug nifedipine. In addition, two compounds, 5b and 5f were more active than the nifedipine.

  DOI：

  10.1016/s0014-827x(03)00159-9