2-methoxy-6-(6-nitro-1H-benzimidazol-2-yl)phenol | 1211402-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-methoxy-6-(6-nitro-1H-benzimidazol-2-yl)phenol
• CAS: 1211402-64-0
• 化学式: C₁₄H₁₁N₃O₄
• 分子量: 285.259
• InChiKey: SLYFOJVTFTYYDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻香草醛 、 4-硝基邻苯二胺 在 sodium metabisulfite 作用下， 以 二甲基亚砜 为溶剂， 以77%的产率得到2-methoxy-6-(6-nitro-1H-benzimidazol-2-yl)phenol
  参考文献：
  名称：

  6-Nitrobenzimidazole derivatives: Potential phosphodiesterase inhibitors: Synthesis and structure–activity relationship

  摘要：

  6-Nitrobenzimidazole derivatives (1-30) synthesized and their phosphodiesterase inhibitory activities determined. Out of thirty tested compounds, ten showed a varying degrees of phosphodiesterase inhibition with IC50 values between 1.5 +/- 0.043 and 294.0 +/- 16.7 mu M. Compounds 30 (IC50 = 1.5 +/- 0.043 mu M), 1 (IC50 = 2.4 +/- 0.049 mu M), 11 (IC50 = 5.7 +/- 0.113 mu M), 13 (IC50 = 6.4 +/- 0.148 mu M), 14 (IC50 = 10.5 +/- 0.51 mu M), 9 (IC50 = 11.49 +/- 0.08 mu M), 3 (IC50 = 63.1 +/- 1.48 mu M), 10 (IC50 = 120.0 +/- 4.47 mu M), and 6 (IC50 = 153.2 +/- 5.6 mu M) showed excellent phosphodiesterase inhibitory activity, much superior to the standard EDTA (IC50 = 274 +/- 0.007 mu M), and thus are potential molecules for the development of a new class of phosphodiesterase inhibitors. Astructure-activity relationship is evaluated. All compounds are characterized by spectroscopic parameters (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.041

文献信息

• 6-Nitrobenzimidazole derivatives: Potential phosphodiesterase inhibitors: Synthesis and structure–activity relationship
  作者：K.M. Khan、Zarbad Shah、V.U. Ahmad、N. Ambreen、M. Khan、M. Taha、F. Rahim、S. Noreen、S. Perveen、M.I. Choudhary、W. Voelter

  DOI：10.1016/j.bmc.2011.12.041

  日期：2012.2

  6-Nitrobenzimidazole derivatives (1-30) synthesized and their phosphodiesterase inhibitory activities determined. Out of thirty tested compounds, ten showed a varying degrees of phosphodiesterase inhibition with IC50 values between 1.5 +/- 0.043 and 294.0 +/- 16.7 mu M. Compounds 30 (IC50 = 1.5 +/- 0.043 mu M), 1 (IC50 = 2.4 +/- 0.049 mu M), 11 (IC50 = 5.7 +/- 0.113 mu M), 13 (IC50 = 6.4 +/- 0.148 mu M), 14 (IC50 = 10.5 +/- 0.51 mu M), 9 (IC50 = 11.49 +/- 0.08 mu M), 3 (IC50 = 63.1 +/- 1.48 mu M), 10 (IC50 = 120.0 +/- 4.47 mu M), and 6 (IC50 = 153.2 +/- 5.6 mu M) showed excellent phosphodiesterase inhibitory activity, much superior to the standard EDTA (IC50 = 274 +/- 0.007 mu M), and thus are potential molecules for the development of a new class of phosphodiesterase inhibitors. Astructure-activity relationship is evaluated. All compounds are characterized by spectroscopic parameters (C) 2011 Elsevier Ltd. All rights reserved.