5,6-Dimethyl-1H-benzo[d]imidazole-2-sulfonic acid | 287730-18-1

• 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: 5,6-Dimethyl-1H-benzo[d]imidazole-2-sulfonic acid
• 英文别名: 5,6-dimethyl-1H-benzimidazole-2-sulfonic acid
• CAS: 287730-18-1
• 化学式: C₉H₁₀N₂O₃S
• 分子量: 226.256
• InChiKey: JFIQLOGXNUXRCY-UHFFFAOYSA-N

物化性质

• 密度：
  1.504±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-Dimethyl-1H-benzo[d]imidazole-2-sulfonic acid 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  N-取代苯并咪唑-2-磺酸的合成及部分转化

  摘要：

  DOI：

  10.1007/s10593-006-0112-4
• 作为产物：
  描述：

  1,3-二氢-5,6-二甲基-2H-苯并咪唑-2-硫酮 在 sodium hydroxide 、 双氧水 作用下， 生成 5,6-Dimethyl-1H-benzo[d]imidazole-2-sulfonic acid
  参考文献：
  名称：

  Benzimidazoles as NMDA Glycine-Site Antagonists: Study on the Structural Requirements in 2-Position of the Ligand

  摘要：

  A series of different substituted benzimidazole derivatives has been synthesized and evaluated for the ability to displace [3H]MDL-105,519 to rat cortical membranes. Two benzimidazole-2-carboxylic acids 9 b and 9 c, in this substitution pattern not yet described as glycine antagonists, showed IC50 values of 0.89 microM (9 b) and 38.0 microM (9 c). Replacement of the carboxylate function in 2-position by a sulfonic acid moiety appreciably increased solubility, but decreased the affinity giving evidence for the strong need of the carboxylate group within the ligand. Further structure-activity studies using benzimidazole-2-one derivatives with an acetic acid moiety adjacent to a ring nitrogen revealed new insights into the importance of amide functionalities within the heterocycle for the affinity of antagonist glycine-site ligands.

  DOI：

  10.1002/(sici)1521-4184(20005)333:5<123::aid-ardp123>3.0.co;2-5

文献信息

• Benzimidazoles as NMDA Glycine-Site Antagonists: Study on the Structural Requirements in 2-Position of the Ligand
  作者：Gerd Dannhardt、Beate K. Kohl

  DOI：10.1002/(sici)1521-4184(20005)333:5<123::aid-ardp123>3.0.co;2-5

  日期：2000.5

  A series of different substituted benzimidazole derivatives has been synthesized and evaluated for the ability to displace [3H]MDL-105,519 to rat cortical membranes. Two benzimidazole-2-carboxylic acids 9 b and 9 c, in this substitution pattern not yet described as glycine antagonists, showed IC50 values of 0.89 microM (9 b) and 38.0 microM (9 c). Replacement of the carboxylate function in 2-position by a sulfonic acid moiety appreciably increased solubility, but decreased the affinity giving evidence for the strong need of the carboxylate group within the ligand. Further structure-activity studies using benzimidazole-2-one derivatives with an acetic acid moiety adjacent to a ring nitrogen revealed new insights into the importance of amide functionalities within the heterocycle for the affinity of antagonist glycine-site ligands.
• COMPOUNDS, COMPOSITIONS COMPRSING SAME, AND METHODS RELATED THERETO
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：US20160115136A1

  公开（公告）日：2016-04-28

  Disclosed herein are compounds, such as benzimidazole derivatives, and composition, such as pharmaceutical compositions, and methods related thereto for treating or preventing microbial infections. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• [EN] COMPOUNDS, COMPOSITIONS COMPRISING SAME, AND METHODS RELATED THERETO<br/>[FR] COMPOSÉS, COMPOSITIONS LES COMPRENANT ET PROCÉDÉS ASSOCIÉS
  申请人：UNIV IOWA RES FOUND

  公开号：WO2014160405A1

  公开（公告）日：2014-10-02

  Discloaed herein are compounds, such as benzimidazole derivatives, and composition, such as pharmaceutical compoistions, and methods related thereto for treating or preventing microbial infections. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• Synthesis and some conversions of N-substituted benzimidazole-2-sulfonic acids
  作者：L. N. Divaeva、T. A. Kuzmenko、A. S. Morkovnik、V. N. Komissarov

  DOI：10.1007/s10593-006-0112-4

  日期：2006.4
• Structure-Based Design of New Dihydrofolate Reductase Antibacterial Agents: 7-(Benzimidazol-1-yl)-2,4-diaminoquinazolines
  作者：Thanh Lam、Mark T. Hilgers、Mark L. Cunningham、Bryan P. Kwan、Kirk J. Nelson、Vickie Brown-Driver、Voon Ong、Michael Trzoss、Grayson Hough、Karen Joy Shaw、John Finn

  DOI：10.1021/jm401204g

  日期：2014.2.13

  A new series of dihydrofolate reductase (DHFR) inhibitors, the 7-(benzimidazol-1-yl)-2,4-diaminoquinazolines, were designed and optimized for antibacterial potency and enzyme selectivity. The most potent inhibitors in this series contained a five-membered heterocycle at the 2-position of, the benzimidazole, leading to highly potent and selective compounds that exploit the differences in the size of a binding pocket adjacent to the NADPH cofactor between the bacterial and human DHFR enzymes. Typical of these compounds is 74(2-thiazol-2-yObenzimidazol-1-yl)-2,4 diaminoquinazoline, which is a potent inhibitor of S. aureus DHFR (K-i = 0.002 nM) with 46700-fold selectivity over human DHFR. This compound also has high antibacterial potency on Gram-positive bacteria with an MIC versus wild type S. aureus of 0.0125 mu g/mL and a MIC versus trimethoprim-resistant S. aureus of 0.25 mu g/mL. In vivo efficacy versus a S. aureus septicemia was demonstrated, highlighting the potential of this new series.