2-(dodecyldisulfanyl)ethyl 2-[(2-naphthylmethyl)(4-{[(tetrahydro-2H-pyran-2-yloxy)amino]carbonyl}benzyl)amino]ethyl carbonate | 1198587-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(dodecyldisulfanyl)ethyl 2-[(2-naphthylmethyl)(4-{[(tetrahydro-2H-pyran-2-yloxy)amino]carbonyl}benzyl)amino]ethyl carbonate
• 英文别名: 2-(Dodecyldisulfanyl)ethyl 2-[naphthalen-2-ylmethyl-[[4-(oxan-2-yloxycarbamoyl)phenyl]methyl]amino]ethyl carbonate
• CAS: 1198587-19-7
• 化学式: C₄₁H₅₈N₂O₆S₂
• 分子量: 739.053
• InChiKey: DTGZBCHDOSTBPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  51
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(dodecyldisulfanyl)ethyl 2-[(2-naphthylmethyl)(4-{[(tetrahydro-2H-pyran-2-yloxy)amino]carbonyl}benzyl)amino]ethyl carbonate 在 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以76%的产率得到DDTS-K-182
  参考文献：
  名称：

  Histone deacetylase inhibitor prodrugs in nanoparticle vector enhanced gene expression in human cancer cells

  摘要：

  We developed histone deacetylase inhibitor (HDACI) prodrugs to enhance the expression of the external genes transfected into human cells with cationic nanoparticles (NPs). We synthesized five kinds of lipid-linked HDACI prodrugs in which n-dodecanoic acid or cholesterol is linked with a potent HDACI, K-182, by an ester bond or a disulfide carbonate linker. The prodrugs were able to admix as a component of NPs, although the intact K-182 was not incorporated into NPs. Namely, NPs composed of cholesteryl-3 beta-carboxyamidoethylene-N-hydroxyethylamine and Tween 80 with the 10 mol% K-182 prodrug were prepared as a DNA vector to transfect plasmid DNAs into human prostate cancer cells, PC-3, or human breast cancer cells, Sk-Br-3. The NPs containing K-182 prodrugs with n-dodecanoic acid exhibited two to four times higher the gene expression than the original NPs. The enhancement of the gene expression will be due to the hyperacetylation of core histories caused by intact K-182 degraded from the prodrug in the vector incorporated into the cells. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.036
• 作为产物：
  描述：

  2-[(2-naphthylmethyl)(4-{[(tetrahydro-2H-pyran-2-yloxy)amino]carbonyl}benzyl)amino] ethyl 2-(2-pyridinyldisulfanyl)ethyl carbonate 、 十二硫醇 以 二甲基亚砜 为溶剂， 反应 2.5h， 以93.9%的产率得到2-(dodecyldisulfanyl)ethyl 2-[(2-naphthylmethyl)(4-{[(tetrahydro-2H-pyran-2-yloxy)amino]carbonyl}benzyl)amino]ethyl carbonate
  参考文献：
  名称：

  Histone deacetylase inhibitor prodrugs in nanoparticle vector enhanced gene expression in human cancer cells

  摘要：

  We developed histone deacetylase inhibitor (HDACI) prodrugs to enhance the expression of the external genes transfected into human cells with cationic nanoparticles (NPs). We synthesized five kinds of lipid-linked HDACI prodrugs in which n-dodecanoic acid or cholesterol is linked with a potent HDACI, K-182, by an ester bond or a disulfide carbonate linker. The prodrugs were able to admix as a component of NPs, although the intact K-182 was not incorporated into NPs. Namely, NPs composed of cholesteryl-3 beta-carboxyamidoethylene-N-hydroxyethylamine and Tween 80 with the 10 mol% K-182 prodrug were prepared as a DNA vector to transfect plasmid DNAs into human prostate cancer cells, PC-3, or human breast cancer cells, Sk-Br-3. The NPs containing K-182 prodrugs with n-dodecanoic acid exhibited two to four times higher the gene expression than the original NPs. The enhancement of the gene expression will be due to the hyperacetylation of core histories caused by intact K-182 degraded from the prodrug in the vector incorporated into the cells. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.036