cyclohexyl carbamo(dithioperoxo)imidate hydrochloride | 1421763-13-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: cyclohexyl carbamo(dithioperoxo)imidate hydrochloride
• 英文别名: Cyclohexylsulfanyl carbamimidothioate;hydrochloride；cyclohexylsulfanyl carbamimidothioate;hydrochloride
• CAS: 1421763-13-4
• 化学式: C₇H₁₄N₂S₂*ClH
• 分子量: 226.794
• InChiKey: ORZYIUPGSYTKOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclohexyl carbamo(dithioperoxo)imidate hydrochloride 、 2-巯基苯并恶唑 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 以87%的产率得到2-(cyclohexyldisulfanyl)benzo[d]oxazole
  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
• 作为产物：
  描述：

  环己硫醇 、 硫脲 在 盐酸 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以90%的产率得到cyclohexyl carbamo(dithioperoxo)imidate hydrochloride
  参考文献：
  名称：

  含有环己基的不对称二硫醚类化合物及其在 制备抗菌药物中的用途

  摘要：

  本发明涉及一类含有环己基的不对称二硫醚类化合物及其在制备抗菌药物中的用途。本发明的含有环己基的不对称二硫醚类化合物对耐甲氧西林金黄色葡萄球菌(MRSA)、金黄色葡萄球菌和白色念珠菌具有很强的抑制作用，可用于制备新型的抗菌药物。这些药物可以制成注射剂、片剂、丸剂、胶囊、悬浮剂或乳剂的形式使用。其给药途径可为口服、经皮，静脉或肌肉注射。

  公开号：

  CN106083726B

文献信息

• 含有环己基的不对称二硫醚类化合物及其在 制备抗菌药物中的用途
  申请人：南开大学

  公开号：CN106083726B

  公开（公告）日：2018-07-10

  本发明涉及一类含有环己基的不对称二硫醚类化合物及其在制备抗菌药物中的用途。本发明的含有环己基的不对称二硫醚类化合物对耐甲氧西林金黄色葡萄球菌(MRSA)、金黄色葡萄球菌和白色念珠菌具有很强的抑制作用，可用于制备新型的抗菌药物。这些药物可以制成注射剂、片剂、丸剂、胶囊、悬浮剂或乳剂的形式使用。其给药途径可为口服、经皮，静脉或肌肉注射。
• 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.