4-(6-nitro-1H-benzimidazol-2-yl)-1,3-benzenediol | 1246840-93-6

• 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: 4-(6-nitro-1H-benzimidazol-2-yl)-1,3-benzenediol
• 英文别名: 4-(6-nitro-1 H-benzimidazol-2-yl)-l,3-benzenediol；4-(6-nitro-1H-benzimidazol-2-yl)benzene-1,3-diol
• CAS: 1246840-93-6
• 化学式: C₁₃H₉N₃O₄
• 分子量: 271.232
• InChiKey: AJHOCTJIPTYGBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基邻苯二胺 、 2,4-二羟基苯甲醛 在 sodium metabisulfite 作用下， 以 二甲基亚砜 为溶剂， 以81%的产率得到4-(6-nitro-1H-benzimidazol-2-yl)-1,3-benzenediol
  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

• Biological Evaluation, Molecular Docking, and SAR Studies of Novel 2-(2,4-Dihydroxyphenyl)-1H- Benzimidazole Analogues
  作者：Joanna Matysiak、Alicja Skrzypek、Monika Karpińska、Kamila Czarnecka、Paweł Szymański、Marek Bajda、Andrzej Niewiadomy

  DOI：10.3390/biom9120870

  日期：——

  In the present study, new 4-(1H-benzimidazol-2-yl)-benzene-1,3-diols, modified in both rings, have been synthesized and their efficacies as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors have been determined. The modified Ellman's spectrophotometric method was applied for the biological evaluation. The compounds showed strong (IC₅₀ 80-90 nM) AChE and moderate (IC₅₀ 5-0.2 µM)

  在本研究中，新的 4-(1H-benzimidazol-2-yl)-benzo-1,3-diols 在两个环中都被修饰，并且它们作为乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BuChE) 抑制剂的功效已经被证实。决定。改进的埃尔曼分光光度法用于生物学评价。这些化合物在体外表现出强 (IC 50 80-90 nM) AChE 和中度 (IC 5-0.2 µM) BuChE 抑制。一些化合物对 AChE/BuChE 有效，与 BuChE 相比表现出高选择性，而其他化合物对两种酶都有活性。讨论了构效关系。这些化合物还能抑制体外自诱导的 Aβ(1-42) 聚集并表现出抗氧化特性。
• US9387198B1
  申请人：——

  公开号：US9387198B1

  公开（公告）日：2016-07-12
• 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.