-benzyl-disulfid | 29673-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: -benzyl-disulfid
• 英文别名: 1-[(Benzyldisulfanyl)methyl]-4-bromobenzene；1-[(benzyldisulfanyl)methyl]-4-bromobenzene
• CAS: 29673-86-7
• 化学式: C₁₄H₁₃BrS₂
• 分子量: 325.293
• InChiKey: YLQHMTFWAAITAI-UHFFFAOYSA-N

物化性质

• 沸点：
  418.1±38.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  -benzyl-disulfid 在 六乙基亚磷酸胺 作用下， 以 苯 为溶剂， 生成 benzyl-(4-bromo-benzyl)-sulfide
  参考文献：
  名称：

  Organic sulfur chemistry. X. Selective desulfurization of disulfides. Scope and mechanism

  摘要：

  DOI：

  10.1021/ja00739a014
• 作为产物：
  描述：

  4-bromobenzyl methanesulfonate 在 lithium aluminium tetrahydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 -benzyl-disulfid
  参考文献：
  名称：

  Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake

  摘要：

  Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide functional group was responsible for the tumor growth inhibitory effects. Cu(I)-assisted radioiodination of benzyl 4-bromobenzyl disulfide gave benzyl 4-[I-123/I-125]iodobenzyl disulfide in 30-40% radiochemical yield. The radiolabeled disulfide was taken up by the cancer cells in a time-dependent manner, and the uptake was inhibited by the pretreatment of S-methyl methanethiosulfonate (MMTS), phorone and diallyl disulfide. This study suggested that the radiolabeled dibenzyl disulfide was taken up by the cancer cells via thiol-disulfide exchange and retained inside the cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.002

文献信息

• Organic sulfur chemistry. X. Selective desulfurization of disulfides. Scope and mechanism
  作者：David N. Harpp、John G. Gleason

  DOI：10.1021/ja00739a014

  日期：1971.5
• Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake
  作者：Eun Kyoung Ryu、Yearn Seong Choe、Sang Sung Byun、Kyung-Han Lee、Dae Yoon Chi、Yong Choi、Byung-Tae Kim

  DOI：10.1016/j.bmc.2004.01.002

  日期：2004.3

  Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide functional group was responsible for the tumor growth inhibitory effects. Cu(I)-assisted radioiodination of benzyl 4-bromobenzyl disulfide gave benzyl 4-[I-123/I-125]iodobenzyl disulfide in 30-40% radiochemical yield. The radiolabeled disulfide was taken up by the cancer cells in a time-dependent manner, and the uptake was inhibited by the pretreatment of S-methyl methanethiosulfonate (MMTS), phorone and diallyl disulfide. This study suggested that the radiolabeled dibenzyl disulfide was taken up by the cancer cells via thiol-disulfide exchange and retained inside the cells. (C) 2004 Elsevier Ltd. All rights reserved.