3-(6-nitro-1 H-benzimidazol-2-yl)-1,2-benzenediol | 1361396-45-3

• 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: 3-(6-nitro-1 H-benzimidazol-2-yl)-1,2-benzenediol
• 英文别名: 3-(6-Nitro-1 h-benzimidazol-2-yl)benzene-1,2-diol；3-(6-nitro-1H-benzimidazol-2-yl)benzene-1,2-diol
• CAS: 1361396-45-3
• 化学式: C₁₃H₉N₃O₄
• 分子量: 271.232
• InChiKey: YHRVPOZUTDVKBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：

  2,3-二羟基苯甲醛 、 4-硝基邻苯二胺 在 sodium metabisulfite 作用下， 以 二甲基亚砜 为溶剂， 以86%的产率得到3-(6-nitro-1 H-benzimidazol-2-yl)-1,2-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

• 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.
• Tavman, Aydin; Birteksoz, A. Seher; Oksuzomer, Faruk, South African Journal of Chemistry, 2012, vol. 65, p. 150 - 158
  作者：Tavman, Aydin、Birteksoz, A. Seher、Oksuzomer, Faruk

  DOI：——

  日期：——
• US9387198B1
  申请人：——

  公开号：US9387198B1

  公开（公告）日：2016-07-12
• One-Pot Synthesis of Benzimidazoles in Water in the Presence of SiO2–OPO3H
  作者：B. F. Mirjalili、A. Bamoniri、M. Rahimi Kazerouni

  DOI：10.1007/s10593-014-1445-z

  日期：2014.4

  Silica-bound phosphoric acid (SiO2-OPO3H), as an eco-friendly, reusable, and heterogeneous catalyst, was applied for synthesis of 2-substituted benzimidazoles in water at 70A degrees C. Very short reaction times, clean work-up, and high yields are among the advantages of this protocol.