3,4,5-triacetoxy-6-(2-nitro-phenyl-carbamoyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester | 1075719-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5-triacetoxy-6-(2-nitro-phenyl-carbamoyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester
• CAS: 1075719-63-9
• 化学式: C₂₀H₂₂N₂O₁₃
• 分子量: 498.4
• InChiKey: ZJUNZNFMTZSCIY-CWLGOENISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  195.9
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3,4,5-triacetoxy-6-(2-nitro-phenyl-carbamoyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 以936 mg的产率得到3,4,5-triacetoxy-6-(2-amino-phenyl-carbamoyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of glucuronide prodrugs of the histone deacetylase inhibitor CI-994 for application in selective cancer chemotherapy

  摘要：

  Two glucuronide prodrugs of the histone deacetylase inhibitor CI-994 were synthesized. These compounds were found to be soluble in aqueous media and stable under physiological conditions. The carbamoyl derivatisation of CI-994 significantly decreased its toxicity towards NCI-H661 lung cancer cells. Prodrug incubation with beta-glucuronidase in the culture media led efficiently to the release of the parent drug and thereby restoring its ability to decrease cell proliferation, to inhibit HDAC and to induce E-Cadherin expression. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.048
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 、 异腈酸2-硝基苯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以86%的产率得到3,4,5-triacetoxy-6-(2-nitro-phenyl-carbamoyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of glucuronide prodrugs of the histone deacetylase inhibitor CI-994 for application in selective cancer chemotherapy

  摘要：

  Two glucuronide prodrugs of the histone deacetylase inhibitor CI-994 were synthesized. These compounds were found to be soluble in aqueous media and stable under physiological conditions. The carbamoyl derivatisation of CI-994 significantly decreased its toxicity towards NCI-H661 lung cancer cells. Prodrug incubation with beta-glucuronidase in the culture media led efficiently to the release of the parent drug and thereby restoring its ability to decrease cell proliferation, to inhibit HDAC and to induce E-Cadherin expression. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.048