(2-(Cyclohexyldisulfanyl)-1H-benzo[d]imidazol-6-yl)(phenyl)-methanone | 1421763-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-(Cyclohexyldisulfanyl)-1H-benzo[d]imidazol-6-yl)(phenyl)-methanone
• 英文别名: [2-(cyclohexyldisulfanyl)-3H-benzimidazol-5-yl]-phenylmethanone
• CAS: 1421763-07-6
• 化学式: C₂₀H₂₀N₂OS₂
• 分子量: 368.524
• InChiKey: TYGGRMZGJNJNDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环己硫醇 在 盐酸 、 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 3.5h， 生成 (2-(Cyclohexyldisulfanyl)-1H-benzo[d]imidazol-6-yl)(phenyl)-methanone
  参考文献：
  名称：

  Selective Inhibition of Extracellular Thioredoxin by Asymmetric Disulfides

  摘要：

  Whereas the role of mammalian thioredoxin (Trx) as an intracellular protein cofactor is widely appreciated, its function in the extracellular environment is not well-understood. Only few extracellular targets of Trx-mediated thiol disulfide exchange are known. For example, Trx activates extracellular transglutaminase 2 (TG2) via reduction of an intramolecular disulfide bond. Because hyperactive TG2 is thought to play a role in various diseases, understanding the biological role of utracellular Trx may provide critical insight into the pathogenesis of these disorders. Starting from a clinical-stage asymmetric disulfide lead, we have identified analogs with >100-fold specificity for Trx. Structure-activity relationship and computational docking model analyses have provided insights into the features important for enhancing potency and specificity. The most active compound identified had an IC50 below 0.1 mu M in cell culture and may be appropriate for in vivo use to interrogate the role of extracellular Trx in health and disease.

  DOI：

  10.1021/jm301775s

文献信息

• Methods and compositions to prevent or treat bacterial infections
  申请人：Ketter Patrick

  公开号：US10398682B2

  公开（公告）日：2019-09-03

  Certain embodiments are directed to methods and compositions for preventing or treating bacterial infections. In certain embodiments the compositions comprise thioredoxin inhibitors, and/or thioredoxin-like inhibitors.

  某些实施方案涉及预防或治疗细菌感染的方法和组合物。在某些实施方案中，组合物包括硫氧还蛋白抑制剂和/或硫氧还蛋白样抑制剂。
• METHODS AND COMPOSITIONS TO PREVENT OR TREAT BACTERIAL INFECTIONS
  申请人：KETTER Patrick

  公开号：US20160151333A1

  公开（公告）日：2016-06-02

  Certain embodiments are directed to methods and compositions for preventing or treating bacterial infections. In certain embodiments the compositions comprise thioredoxin inhibitors, and/or thioredoxin-like inhibitors.
• [EN] METHODS AND COMPOSITIONS TO PREVENT OR TREAT BACTERIAL INFECTIONS<br/>[FR] MÉTHODES ET COMPOSITIONS DESTINÉES À PRÉVENIR OU TRAITER LES INFECTIONS BACTÉRIENNES
  申请人：KETTER PATRICK

  公开号：WO2015009699A1

  公开（公告）日：2015-01-22

  Certain embodiments are directed to methods and compositions for preventing or treating bacterial infections. In certain embodiments the compositions comprise thioredoxin inhibitors, and/or thioredoxin-like inhibitors.
• [EN] METHODS AND COMPOSITIONS TO PREVENT OR TREAT BACTERIAL INFECTIONS<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR PRÉVENIR OU TRAITER DES INFECTIONS BACTÉRIENNES
  申请人：KETTER PATRICK

  公开号：WO2017004545A1

  公开（公告）日：2017-01-05

  Certain embodiments are directed to methods and compositions for preventing treating bacterial infections. In certain embodiments the compositions comprise thioredoxin deficient bacteria.
• Selective Inhibition of Extracellular Thioredoxin by Asymmetric Disulfides
  作者：Thomas R. DiRaimondo、Nicholas M. Plugis、Xi Jin、Chaitan Khosla

  DOI：10.1021/jm301775s

  日期：2013.2.14

  Whereas the role of mammalian thioredoxin (Trx) as an intracellular protein cofactor is widely appreciated, its function in the extracellular environment is not well-understood. Only few extracellular targets of Trx-mediated thiol disulfide exchange are known. For example, Trx activates extracellular transglutaminase 2 (TG2) via reduction of an intramolecular disulfide bond. Because hyperactive TG2 is thought to play a role in various diseases, understanding the biological role of utracellular Trx may provide critical insight into the pathogenesis of these disorders. Starting from a clinical-stage asymmetric disulfide lead, we have identified analogs with >100-fold specificity for Trx. Structure-activity relationship and computational docking model analyses have provided insights into the features important for enhancing potency and specificity. The most active compound identified had an IC50 below 0.1 mu M in cell culture and may be appropriate for in vivo use to interrogate the role of extracellular Trx in health and disease.