Bis-(4-p-tolylsulfonamidophenyl)disulfid | 14817-57-3

• 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: Bis-(4-p-tolylsulfonamidophenyl)disulfid
• 英文别名: 4-methyl-N-[4-[[4-[(4-methylphenyl)sulfonylamino]phenyl]disulfanyl]phenyl]benzenesulfonamide
• CAS: 14817-57-3
• 化学式: C₂₆H₂₄N₂O₄S₄
• 分子量: 556.752
• InChiKey: RHCQFJQOQYHYRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Bis-(4-p-tolylsulfonamidophenyl)disulfid 在 氢溴酸 、 potassium carbonate 、 苯酚 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1,2,21,22-tetrathia-9,14,29,34-tetraaza[6.2.6.2]paracyclophane
  参考文献：
  名称：

  Synthesis, Guest-Binding, and Reduction-Responsive Degradation Properties of Water-Soluble Cyclophanes Having Disulfide Moieties

  摘要：

  Water-soluble cationic cyclophane having diphenyl disulfide moieties (1a) was synthesized as a reduction-responsive degradable host. The stoichiometry for the complex of 1a with anionic fluorescence guests, such as 4,4'-bis(1-anilinonaphthalene-8-sulfonate) (Bis-ANS) and 4-(1-pyrene)-butanoic acid (PBA), was confirmed to be 1:1 host:guest by a Job plot. The binding constants (K) of 1a toward Bis-ANS and PBA were evaluated to be 6.7 x 10(3) and 4.5 x 10(4) M-1, respectively, as confirmed by fluorescence spectroscopy. Reduction of disulfide bonds of 1a by dithiothreitol gave its reduced form having poor guest-binding affinity that led to release of the entrapped guest molecules to the bulk aqueous phase. Meanwhile, anionic cyclophane 1b, which was derived from 1a by a reaction with succinic anhydride, binds cationic anticancer drugs, such as daunorubicin hydrochloride (DNR) and doxorubicin hydrochloride (DOX), with a K of 2.1 x 10(3) and 7.5 x 10(2) M-1, respectively. A similar reduction-responsive guest release feature was observed when DNR and DOX were employed as a guest for complexation with 1b.

  DOI：

  10.1021/jo400591w
• 作为产物：
  描述：

  4,4'-二氨基二苯二硫醚 、 对甲苯磺酰氯 在 吡啶 作用下， 生成 Bis-(4-p-tolylsulfonamidophenyl)disulfid
  参考文献：
  名称：

  Synthesis, Guest-Binding, and Reduction-Responsive Degradation Properties of Water-Soluble Cyclophanes Having Disulfide Moieties

  摘要：

  Water-soluble cationic cyclophane having diphenyl disulfide moieties (1a) was synthesized as a reduction-responsive degradable host. The stoichiometry for the complex of 1a with anionic fluorescence guests, such as 4,4'-bis(1-anilinonaphthalene-8-sulfonate) (Bis-ANS) and 4-(1-pyrene)-butanoic acid (PBA), was confirmed to be 1:1 host:guest by a Job plot. The binding constants (K) of 1a toward Bis-ANS and PBA were evaluated to be 6.7 x 10(3) and 4.5 x 10(4) M-1, respectively, as confirmed by fluorescence spectroscopy. Reduction of disulfide bonds of 1a by dithiothreitol gave its reduced form having poor guest-binding affinity that led to release of the entrapped guest molecules to the bulk aqueous phase. Meanwhile, anionic cyclophane 1b, which was derived from 1a by a reaction with succinic anhydride, binds cationic anticancer drugs, such as daunorubicin hydrochloride (DNR) and doxorubicin hydrochloride (DOX), with a K of 2.1 x 10(3) and 7.5 x 10(2) M-1, respectively. A similar reduction-responsive guest release feature was observed when DNR and DOX were employed as a guest for complexation with 1b.

  DOI：

  10.1021/jo400591w

文献信息

• POLYMER FOR HEAT-SENSITIVE LITHOGRAPHIC PRINTING PLATE PRECURSOR
  申请人：Agfa Graphics N.V.

  公开号：EP1554347B1

  公开（公告）日：2007-05-30
• US7455949B2
  申请人：——

  公开号：US7455949B2

  公开（公告）日：2008-11-25