(+/-)-trans-4-hydroxy-5-methoxy-1,2-dithiane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: (+/-)-trans-4-hydroxy-5-methoxy-1,2-dithiane
• 英文别名: (4R/S,5R/S)-5-methoxy-1,2-dithian-4-ol；(4SR,5SR)-5-methoxy-1,2-dithian-4-ol；(4S,5S)-5-methoxydithian-4-ol
• 化学式: C₅H₁₀O₂S₂
• 分子量: 166.265
• InChiKey: OMXJSIIQCASGNT-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-4-hydroxy-5-methoxy-1,2-dithiane 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (+/)-2-[2-[2-[(trans-5'-methoxy-1',2'-dithian-4'-yl)oxy]ethoxy]ethoxy]ethanol
  参考文献：
  名称：

  Synthesis and Characterization of SAMs and Tethered Bilayer Membranes from Unsymmetrically Substituted 1,2-Dithianes

  摘要：

  本文介绍了一系列新的成膜化合物的合成过程，这些化合物是基于以前在离子通道开关（ICS）生物传感器（《自然》，1997 年，387，580 期）中使用的成熟成分。所有新化合物都来自 4,5-二羟基-1,2-二噻烷，并包含亲水储层部分（基于乙二醇单元）和亲锂部分（基于天然脂质植物醇）。椭偏仪和接触角测量结果表明，由新材料形成的自组装单层（SAM）的厚度和膜填料与之前报道的生物传感器元件相当。利用离子载体缬氨霉素的阻抗光谱法研究了含有新型材料的系链双层脂膜（t-BLMs）。t-BLMs 的电学行为和计算膜厚度与从标准 ICS 成分得出的结果相当，这表明新型成膜化合物能形成稳定的膜，其流动性足以在缬霉素存在时传输钾离子。

  DOI：

  10.1071/ch05175
• 作为产物：
  描述：

  (4S,5S)-1,2-二噻烷-4,5-二醇 、 硫酸二甲酯 在 四丁基硫酸氢铵 、 potassium hydroxide 作用下， 以 2-甲基四氢呋喃 、 水 为溶剂， 以40.3%的产率得到(+/-)-trans-4-hydroxy-5-methoxy-1,2-dithiane
  参考文献：
  名称：

  Cyclic-Disulfide-Based Prodrugs for Cytosol-Specific Drug Delivery

  摘要：

  AbstractThe cytosolic conversion of therapeutically relevant nucleosides into bioactive triphosphates is often hampered by the inefficiency of the first kinase‐mediated step. Nucleoside monophosphate prodrugs can be used to bypass this limitation. Herein we describe a novel cyclic‐disulfide class of nucleoside monophosphate prodrugs with a cytosol‐specific, reductive release trigger. The key event, a charge‐dissipating reduction‐triggered cyclodeesterification leads to robust cytosolic production of the cyclic 3′,5′‐monophosphate for downstream enzymatic processing. The antiviral competence of the platform was demonstrated with an O‐benzyl‐1,2‐dithiane‐4,5‐diol ester of 2′‐C‐methyluridine‐3′,5′‐phosphate. Both in vitro and in vivo comparison with the clinically efficacious ProTide prodrug of 2′‐deoxy‐2′‐α‐fluoro‐β‐C‐methyluridine is provided. The cytosolic specificity of the release allows for a wide range of potential applications, from tissue‐targeted drug delivery to intracellular imaging.

  DOI：

  10.1002/anie.201407130

文献信息

• Synthesis and Characterization of SAMs and Tethered Bilayer Membranes from Unsymmetrically Substituted 1,2-Dithianes
  作者：Christopher J. Burns、Leslie D. Field、Brian J. Petteys、Damon D. Ridley

  DOI：10.1071/ch05175

  日期：——

  The synthesis of a series of new membrane-forming compounds, based on previously established components used in an ion-channel switch (ICS) biosensor (Nature 1997, 387, 580) is described. All new compounds are derived from 4,5-dihydroxy-1,2-dithiane, and contain a hydrophilic reservoir section (based on ethylene glycol units) and a lypophilic section (based on the natural lipid phytanol). Ellipsometry and contact angle measurements indicate that self-assembled monolayers (SAMs) formed from the new materials possess thicknesses and membrane packing comparable to previously reported biosensor components. Tethered bilayer lipid membranes (t-BLMs) incorporating the novel materials were studied using impedance spectroscopy with the ion-carrier valinomycin. The electrical behavior and calculated membrane thickness of the t-BLMs are comparable to those derived from the standard ICS components and this demonstrates that the novel membrane-forming compounds form stable membranes that are sufficiently fluid to transport potassium ions in the presence of valinomycin.

  本文介绍了一系列新的成膜化合物的合成过程，这些化合物是基于以前在离子通道开关（ICS）生物传感器（《自然》，1997 年，387，580 期）中使用的成熟成分。所有新化合物都来自 4,5-二羟基-1,2-二噻烷，并包含亲水储层部分（基于乙二醇单元）和亲锂部分（基于天然脂质植物醇）。椭偏仪和接触角测量结果表明，由新材料形成的自组装单层（SAM）的厚度和膜填料与之前报道的生物传感器元件相当。利用离子载体缬氨霉素的阻抗光谱法研究了含有新型材料的系链双层脂膜（t-BLMs）。t-BLMs 的电学行为和计算膜厚度与从标准 ICS 成分得出的结果相当，这表明新型成膜化合物能形成稳定的膜，其流动性足以在缬霉素存在时传输钾离子。
• Cyclic-Disulfide-Based Prodrugs for Cytosol-Specific Drug Delivery
  作者：Gabor Butora、Ning Qi、Wenlang Fu、Truyen Nguyen、Hsueh-Cheng Huang、Ian W. Davies

  DOI：10.1002/anie.201407130

  日期：2014.12.15

  AbstractThe cytosolic conversion of therapeutically relevant nucleosides into bioactive triphosphates is often hampered by the inefficiency of the first kinase‐mediated step. Nucleoside monophosphate prodrugs can be used to bypass this limitation. Herein we describe a novel cyclic‐disulfide class of nucleoside monophosphate prodrugs with a cytosol‐specific, reductive release trigger. The key event, a charge‐dissipating reduction‐triggered cyclodeesterification leads to robust cytosolic production of the cyclic 3′,5′‐monophosphate for downstream enzymatic processing. The antiviral competence of the platform was demonstrated with an O‐benzyl‐1,2‐dithiane‐4,5‐diol ester of 2′‐C‐methyluridine‐3′,5′‐phosphate. Both in vitro and in vivo comparison with the clinically efficacious ProTide prodrug of 2′‐deoxy‐2′‐α‐fluoro‐β‐C‐methyluridine is provided. The cytosolic specificity of the release allows for a wide range of potential applications, from tissue‐targeted drug delivery to intracellular imaging.