2-Decyldisulfanyl-1H-imidazole | 141400-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Decyldisulfanyl-1H-imidazole
• 英文别名: 2-(Decyldisulfanyl)-1H-imidazole；2-(decyldisulfanyl)-1H-imidazole
• CAS: 141400-60-4
• 化学式: C₁₃H₂₄N₂S₂
• 分子量: 272.479
• InChiKey: DNYLGTSNAQIWKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  、 2-巯基咪唑 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以66%的产率得到2-Decyldisulfanyl-1H-imidazole
  参考文献：
  名称：

  Synthesis and evaluation of imidazolyl disulfides for selective cytotoxicity to hypoxic EMT6 tumor cells in vitro

  摘要：

  Two series of disulfides were synthesized and evaluated in vitro for selective hypoxic tumor cell cytotoxicity using EMT6 cells. While the series of alkyl 5-nitrobenzimidazolyl disulfides displayed no selectivity, two alkyl imidazolyl disulfides, devoid of a nitro function, showed preferential toxicity to EMT6 cells treated under hypoxic conditions. Select agents of the alkyl imidazolyl series were found to deplete cellular glutathione (GSH) while the corresponding alkyl nitrobenzimidazolyl derivatives did not. One disulfide displaying selective hypoxic cell toxicity, n-butyl 2-imidazolyl disulfide, 10, caused significantly greater depletion of GSH under aerobic conditions. Removal of cellular GSH with buthionine sulfoximine (BSO) prior to exposure to 10 caused an increase in its toxicity and a loss of any differential between aerobic and hypoxic conditions. It is speculated that the diminished aerobic vs hypoxic toxicity of the agent toward EMT6 cells is due to a greater ability of 10 to interact with GSH under aerobic conditions as reflected by the greater GSH depletion.

  DOI：

  10.1016/0223-5234(92)90057-8

文献信息

• METHODS OF PATIENT SELECTION AND TREATING TRXR- OR PRDX-OVEREXPRESSED CANCERS
  申请人：Triact Therapeutics, Inc.

  公开号：EP3654958A1

  公开（公告）日：2020-05-27
• METHODS AND MATERIALS FOR ASSESSING HYDROGEN PEROXIDE ACCUMULATION IN CELLS
  申请人：Mayo Foundation for Medical Education and Research

  公开号：US20180172712A1

  公开（公告）日：2018-06-21

  This document provides methods and materials for assessing hydrogen peroxide accumulation within cells (e.g., cancer cells) exposed to one or more test agents. For example, methods and materials for determining whether or not cancer cells (e.g., MM cells) from a mammal (e.g., a human) accumulate hydrogen peroxide following contact with a test agent (e.g., an IMID) and exogenous H 2 O 2 are provided.
• [EN] METHODS AND MATERIALS FOR ASSESSING HYDROGEN PEROXIDE ACCUMULATION IN CELLS<br/>[FR] PROCÉDÉS ET MATÉRIAUX D'ÉVALUATION DE L'ACCUMULATION DE PEROXYDE D'HYDROGÈNE DANS DES CELLULES
  申请人：MAYO FOUNDATION

  公开号：WO2016205538A1

  公开（公告）日：2016-12-22

  This document provides methods and materials for assessing hydrogen peroxide accumulation within cells (e.g., cancer cells) exposed to one or more test agents. For example, methods and materials for determining whether or not cancer cells (e.g., MM cells) from a mammal (e.g., a human) accumulate hydrogen peroxide following contact with a test agent (e.g., an IMID) and exogenous H2O2 are provided.
• [EN] METHODS OF PATIENT SELECTION AND TREATING TRXR- OR PRDX-OVEREXPRESSED CANCERS<br/>[FR] MÉTHODES DE SÉLECTION DE PATIENTS ET DE TRAITEMENT DE CANCERS SUREXPRIMANT TRXR OU PRDX
  申请人：TRIACT THERAPEUTICS INC

  公开号：WO2018237344A1

  公开（公告）日：2018-12-27

  Disclosed herein are methods and compounds for treating a cancer is characterized with an elevated expression of thioredoxin reductase (TrxR) or an elevated expression of peroxiredoxin (PRDX). In some embodiments, also disclosed herein are methods of selecting subjects for treatment or monitoring the treatment progress based on a biomarker panel.