5-tert-butyl-2-mercapto-1H-benzimidazole | 92806-76-3

• 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: 5-tert-butyl-2-mercapto-1H-benzimidazole
• 英文别名: 2-mercapto-5-tert-butylbenzimidazole；5-tert-butyl-1,3-dihydrobenzimidazole-2-thione
• CAS: 92806-76-3
• 化学式: C₁₁H₁₄N₂S
• 分子量: 206.312
• InChiKey: RHDZGEJUPKAHEK-UHFFFAOYSA-N

物化性质

• 沸点：
  303.1±35.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-2-mercapto-1H-benzimidazole 在 Rose Bengal sodium salt 、 水 、 氧气 、 sodium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以83%的产率得到5-(tert-butyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  可见光诱导的亚硫酰基对2-巯基苯并咪唑的好氧氧化脱硫

  摘要：

  发现温和的不含过渡金属的无毒需氧光氧化还原系统可实现2-巯基苯并咪唑的高效脱硫。这种可行的催化系统包括低催化剂含量的Rose Bengal作为光敏剂，以及廉价的无毒NaCl（催化量）作为添加剂，并与氧气气氛相结合。该方案提供了重要的替代途径，可以以通常的高收率获得各种苯并咪唑和氘代苯并咪唑产品，并且对各种合成和药学上有用的功能具有良好的耐受性。机理研究表明，单电子转移和能量转移都可能在初始步骤发生，并且亚硫酰基自由基中间体参与了关键的脱硫过程。

  DOI：

  10.1039/d0gc02269a
• 作为产物：
  描述：

  N-(4-叔丁基-2-硝基苯基)乙酰胺 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 12.5h， 生成 5-tert-butyl-2-mercapto-1H-benzimidazole
  参考文献：
  名称：

  Structure-Activity Relationship of Omeprazole and Analogs as Helicobacter pylori Urease Inhibitors

  摘要：

  Helicobacter pylori urease belongs to a family of highly conserved urea-hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K(+)-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K(+)-ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pKa-value of the pyridine, the pKa-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of beta-mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 mumol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 mumol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.

  DOI：

  10.1021/jm00025a008

文献信息

• PYRAZOLE-OXAZOLIDINONE COMPOUND FOR ANTI-HEPATITIS B VIRUS
  申请人：Shanghai Zhimeng Biophama Co., Ltd.

  公开号：US20190152963A1

  公开（公告）日：2019-05-23

  The present invention discloses a pyrazole-oxazolidinone compound having anti-hepatitis B virus activity, which has the structure of formula (I), wherein each variable is as defined herein.

  本发明公开了一种具有抗乙型肝炎病毒活性的吡唑-噁唑烷酮化合物，其具有如下式（I）的结构，其中每个变量如本文所定义。
• Structure−Activity Relationship of 2-[[(2-Pyridyl)methyl]thio]-1<i>H</i>- benzimidazoles as Anti <i>Helicobacter pylori </i>Agents in Vitro and Evaluation of their in Vivo Efficacy
  作者：Thomas C. Kühler、Marianne Swanson、Vladimir Shcherbuchin、Håkan Larsson、Björn Mellgård、Jan-Eric Sjöström

  DOI：10.1021/jm970165r

  日期：1998.5.1

  A relationship between the structure of 21 2-[[(2-pyridyl)methyl]thio]-1H-benzimidazoles (6) and their anti Helicobacter pylori activity expressed as minimum bactericidal concentration (MBC) values is described. Observed MBCs ranged from 256 to 1 microg/mL. The structure-activity relationship (SAR) showed that larger and more lipophilic compounds, especially compounds with such substituents in the

  描述了21个2-[[[（2-吡啶基）甲基]硫基] -1H-苯并咪唑类化合物（6）的结构与其以最小杀菌浓度（MBC）值表示的抗幽门螺杆菌活性之间的关系。观察到的MBC范围为256至1微克/毫升。结构-活性关系（SAR）表明，更大和更多的亲脂性化合物，特别是在吡啶基部分的4-位具有这种取代基的化合物，通常具有较低的MBC值。合成并测试了通过建立的SAR模型预测可能有效的四种新化合物。测试了一种这样的化合物，即2-[[（（[4-[（环丙基甲基）氧基] -3-甲基-2-吡啶基）甲基]硫代] -1H-苯并咪唑（18）在小鼠体内的功效。幽门螺杆菌模型（125 micromol / kg口服，持续4天，n = 4）。很遗憾，该模型不能清楚地证明其抗菌活性。相反，观察到有效的酸分泌抑制作用。该发现归因于甲硫基化合物在体内被氧化成相应的甲基亚磺酰基衍生物，即质子泵抑制剂。尽管该抗菌活性具有体内降低粪便链球菌
• Design, synthesis, and biological evaluation of novel pleuromutilin derivatives containing benzimidazoles as effective anti‐MRSA agents
  作者：Qi‐Wen Zhang、Jie Ren、Jia‐Xun Lu、Xiao‐Ying Chen、Xian‐Jin He、Qi Wang、Zi‐Dan Zhou、Zhen Jin、Zhen‐Ling Zeng、You‐Zhi Tang

  DOI：10.1002/ddr.22095

  日期：2023.11

  A series of pleuromutilin derivatives containing benzimidazole were designed, synthesized, and evaluated for their antibacterial activities against Methicillin-resistant Staphylococcus aureus (MRSA) in this study. The in vitro antibacterial activities of the synthesized derivatives against four strains of S. aureus (MRSA ATCC 43300, S. aureus ATCC 29213, S. aureus 144, and S. aureus AD3) were determined

  本研究设计、合成了一系列含有苯并咪唑的截短侧耳素衍生物，并评价了其对耐甲氧西林金黄色葡萄球菌（MRSA）的抗菌活性。通过肉汤稀释法测定了合成衍生物对四种金黄色葡萄球菌菌株（MRSA ATCC 43300、金黄色葡萄球菌ATCC 29213、金黄色葡萄球菌144 和金黄色葡萄球菌AD3）的体外抗菌活性。在这些衍生物中，化合物58对MRSA（最低抑菌浓度[MIC] = 0.0625 μg/mL）表现出优于泰妙菌素（MIC = 0.5 μg/mL）的体外抗菌作用。与泰妙菌素相比，化合物58对MRSA具有更快的杀菌动力学和更长的抗生素后作用时间。同时，在8 μg/mL浓度下，化合物58对RAW 264.7细胞没有表现出明显的细胞毒作用。此外，在减少小鼠大腿感染模型中的 MRSA 负荷方面，化合物58 (-2.04 log 10 CFU/mL) 表现出比泰妙菌素 (-1.02 log 10 CFU/mL)
• Anti-viral compounds
  申请人：AbbVie Inc.

  公开号：US10028937B2

  公开（公告）日：2018-07-24

  Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.

  本发明描述了有效抑制丙型肝炎病毒（"HCV"）复制的化合物。本发明还涉及制造此类化合物的工艺、包含此类化合物的组合物以及使用此类化合物治疗 HCV 感染的方法。
• Madsen, Peter; Knudsen, Lotte B.; Wiberg, Finn C., Journal of Medicinal Chemistry, 1998, vol. 41, # 26, p. 5150 - 5157
  作者：Madsen, Peter、Knudsen, Lotte B.、Wiberg, Finn C.、Carr, Richard D.

  DOI：——

  日期：——