2-(cyclohexyldisulfanyl)-1H-benzo[d]imidazole | 40952-49-6

• 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: 2-(cyclohexyldisulfanyl)-1H-benzo[d]imidazole
• 英文别名: 2-(Cyclohexyldithio)-benzimidazol；2-cyclohexyldisulfanyl-1H-benzoimidazole；2-(cyclohexyldithio)benzimidazole；2-(cyclohexyldisulfanyl)-1H-benzimidazole
• CAS: 40952-49-6
• 化学式: C₁₃H₁₆N₂S₂
• 分子量: 264.415
• InChiKey: XXLFTWNQPCRCES-UHFFFAOYSA-N

物化性质

• 沸点：
  468.0±28.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  3

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]imidazole
  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

• Synthesis and biological evaluation of disulfides as anticancer agents with thioredoxin inhibition
  作者：Xiangxu Wei、Miao Zhong、Song Wang、Lexun Li、Zi-Long Song、Junmin Zhang、Jianqiang Xu、Jianguo Fang

  DOI：10.1016/j.bioorg.2021.104814

  日期：2021.5

  these compounds, 8 compounds showed significant inhibition activity against Trx. We then evaluated the cytotoxicity of these 8 disulfides, compounds 68 and 69 displayed high cytotoxicity to HeLa cells, but less sensitive to normal cell lines. Next, we performed kinetic studies of both two disulfides, 68 had faster inhibition of Trx than 69. Further studies revealed that 68 led to the accumulation of reactive

  改变氧化还原稳态作为癌细胞的标志被癌细胞用于生长和存活。硫氧还蛋白 (Trx) 是维持细胞内氧化还原稳态的重要调节剂，被广泛认为是开发抗癌药物的有希望的靶点。在此，我们合成了 72 种二硫化物并评估了它们 对 Trx 和抗肿瘤活性的抑制作用。首先，我们建立了一种高效快速的筛选Trx抑制剂的方法，利用我们团队开发的探针NBL-SS来检测活细胞中的Trx功能。在对这些化合物的 Trx 抑制活性进行初步筛选后，8 种化合物对 Trx 显示出显着的抑制活性。然后我们评估了这 8 种二硫化物、化合物68和69的细胞毒性对 HeLa 细胞显示出高细胞毒性，但对正常细胞系不太敏感。接下来，我们对两种二硫化物进行了动力学研究，68比69对 Trx 的抑制更快。进一步的研究表明，68导致活性氧的积累，并最终通过抑制 Trx诱导 Hela 细胞凋亡。筛选Trx抑制剂的方法的建立和具有显着Trx抑制作用的68的
• Isocyanate composition
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0042701A2

  公开（公告）日：1981-12-30

  O isocyanate composition which is superior in stability and reactivity, wherein at least one additive selected from the group consisting of peroxides, sulfur, polysulfides, metal sulfides and halogens is added to a reaction product of organic isocyanate and carbon dioxide in an amount of 0.001 to 10% by weight based on the starting isocyanate.

  O 型异氰酸酯组合物具有更高的稳定性和反应活性，其中至少一种添加剂选自过氧化物、硫磺、多硫化物、金属硫化物和卤素组成的组，添加到有机异氰酸酯和二氧化碳的反应产物中，添加量为起始异氰酸酯的 0.001 至 10%（按重量计）。
• 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。
• Modulation of Tissue Transglutaminase Activation in Disease
  申请人：DiRaimondo Thomas

  公开号：US20140322278A1

  公开（公告）日：2014-10-30

  Compositions and methods are provided for modulating the physiological activation of tissue transglutaminase (TG2); which methods can include inhibiting the activation of TG2 associated with enteric inflammatory disorders, which disorders may include celiac disease, irritable bowel syndrome, Crohn's Disease, dermatitis herpetiformis, and the like. In other embodiments of the invention, methods are provided for reducing undesirable paracellular transport in enteric tissues, in particular the paracellular transport of molecules greater than about 500 mw, e.g. peptides, including without limitation immunogenic gluten peptides.
• 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.