2-(2-butyldisulfanyl)ethanol

• 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: 2-(2-butyldisulfanyl)ethanol
• 英文别名: 2-(Butyldisulfanyl)ethanol；2-(butyldisulfanyl)ethanol
• 化学式: C₆H₁₄OS₂
• 分子量: 166.309
• InChiKey: LOLOFXUGVQGLHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三光气 、 2-(2-butyldisulfanyl)ethanol 、 7-乙基-10-羟基喜树碱 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以84.8 %的产率得到
  参考文献：
  名称：

  Disulfide Bond-Based SN38 Prodrug Nanoassemblies with High Drug Loading and Reduction-Triggered Drug Release for Pancreatic Cancer Therapy

  摘要：

  Purpose: Chemotherapy is a significant and effective therapeutic strategy that is frequently utilized in the treatment of cancer. Small molecular prodrug-based nanoassemblies (SMPDNAs) combine the benefits of both prodrugs and nanomedicine into a single nanoassembly with high drug loading, increased stability, and improved biocompatibility. Methods: In this study, a disulfide bond inserted 7-ethyl-10-hydroxycamptothecin (SN38) prodrug was rationally designed and then used to prepare nanoassemblies (SNSS NAs) that were selectively activated by rich glutathione (GSH) in the tumor site. The characterization of SNSS NAs and the in vitro and in vivo evaluation of their antitumor effect on a pancreatic cancer model were performed. Results: In vitro findings demonstrated that SNSS NAs exhibited GSH-induced SN38 release and cytotoxicity. SNSS NAs have demonstrated a passive targeting effect on tumor tissues, a superior antitumor effect compared to irinotecan (CPT-11), and satisfactory biocompatibility with double dosage treatment. Conclusion: The SNSS NAs developed in this study provide a new method for the preparation of SN38-based nano-delivery systems with improved antitumor effect and biosafety.

  DOI：

  10.2147/ijn.s404848
• 作为产物：
  描述：

  丁硫醇 、 2-巯基乙醇 在 三氯异氰尿酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.08h， 以67%的产率得到2-(2-butyldisulfanyl)ethanol
  参考文献：
  名称：

  利用TCCA有效地一锅构建不对称二硫键

  摘要：

  我们在这里报告了不对称二硫化物的一锅法合成，其中三氯异氰尿酸（TCCA）为氧化剂。在方便的条件下，即使没有碱，也能以良好至极好的收率合成芳族-芳族二硫化物和芳族-脂族二硫化物。为了构建具有挑战性的脂族-脂肪族二硫化物，还可以在条件略微改变的情况下获得所需产物的良好收率。此外，反应证明了广泛的底物范围，非常短的反应时间（<5分钟）和简便的程序。

  DOI：

  10.1016/j.tetlet.2016.12.007

文献信息

• Efficient one-pot construction of unsymmetrical disulfide bonds with TCCA
  作者：Feng Yang、Wen Wang、Kaidi Li、Weili Zhao、Xiaochun Dong

  DOI：10.1016/j.tetlet.2016.12.007

  日期：2017.1

  We report herein a one-pot synthesis of unsymmetrical disulfides with trichloroisocyanuric acid (TCCA) as an oxidant. Under facile conditions, aromatic-aromatic disulfides and aromatic-aliphatic disulfides were synthesized in good to excellent yields even without base. For the construction of the challenging aliphatic-aliphatic disulfides, good yields of the desired products were also obtained with

  我们在这里报告了不对称二硫化物的一锅法合成，其中三氯异氰尿酸（TCCA）为氧化剂。在方便的条件下，即使没有碱，也能以良好至极好的收率合成芳族-芳族二硫化物和芳族-脂族二硫化物。为了构建具有挑战性的脂族-脂肪族二硫化物，还可以在条件略微改变的情况下获得所需产物的良好收率。此外，反应证明了广泛的底物范围，非常短的反应时间（<5分钟）和简便的程序。
• Disulfide Bond-Based SN38 Prodrug Nanoassemblies with High Drug Loading and Reduction-Triggered Drug Release for Pancreatic Cancer Therapy
  作者：Zhi-Xin Zhong、Xu-Zhao Li、Jin-Tao Liu、Nan Qin、Hong-Quan Duan、Xiao-Chuan Duan

  DOI：10.2147/ijn.s404848

  日期：——

  Purpose: Chemotherapy is a significant and effective therapeutic strategy that is frequently utilized in the treatment of cancer. Small molecular prodrug-based nanoassemblies (SMPDNAs) combine the benefits of both prodrugs and nanomedicine into a single nanoassembly with high drug loading, increased stability, and improved biocompatibility. Methods: In this study, a disulfide bond inserted 7-ethyl-10-hydroxycamptothecin (SN38) prodrug was rationally designed and then used to prepare nanoassemblies (SNSS NAs) that were selectively activated by rich glutathione (GSH) in the tumor site. The characterization of SNSS NAs and the in vitro and in vivo evaluation of their antitumor effect on a pancreatic cancer model were performed. Results: In vitro findings demonstrated that SNSS NAs exhibited GSH-induced SN38 release and cytotoxicity. SNSS NAs have demonstrated a passive targeting effect on tumor tissues, a superior antitumor effect compared to irinotecan (CPT-11), and satisfactory biocompatibility with double dosage treatment. Conclusion: The SNSS NAs developed in this study provide a new method for the preparation of SN38-based nano-delivery systems with improved antitumor effect and biosafety.