6-(3,4-dimethoxybenzoyloxy)-3,4,5-tris(triethylsilanyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester | 1075719-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(3,4-dimethoxybenzoyloxy)-3,4,5-tris(triethylsilanyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester
• CAS: 1075719-66-2
• 化学式: C₃₄H₆₄O₉Si₃
• 分子量: 701.133
• InChiKey: OSIAJGNEMNYQFW-FVRGGSDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  46.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-(3,4-dimethoxybenzoyloxy)-3,4,5-tris(triethylsilanyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以90%的产率得到6-hydroxy-3,4,5-tris(triethylsilanyloxy)-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：

  三乙基硅基三氟甲磺酸酯 、 methyl (2S,3S,4S,5R,6R)-6-[(3,4-dimethoxyphenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以7.85 g的产率得到6-(3,4-dimethoxybenzoyloxy)-3,4,5-tris(triethylsilanyloxy)-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