6-[2-(4-acetylamino-benzoylamino)-phenylcarbamoyloxy]-3,4,5-tris(triethylsilanyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester | 1075719-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[2-(4-acetylamino-benzoylamino)-phenylcarbamoyloxy]-3,4,5-tris(triethylsilanyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester
• CAS: 1075719-70-8
• 化学式: C₄₁H₆₇N₃O₁₀Si₃
• 分子量: 846.254
• InChiKey: CXHJZCBVYICSDR-NWVMSOAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.51
• 重原子数：
  57.0
• 可旋转键数：
  21.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  159.75
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-[2-(4-acetylamino-benzoylamino)-phenylcarbamoyloxy]-3,4,5-tris(triethylsilanyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester 在 甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 14.0h， 以78%的产率得到6-[2-(4-acetylamino-benzoylamino)-phenylcarbamoyloxy]-3,4,5-trihydroxy-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：

  6-(2-amino-phenylcarbamoyloxy)-3,4,5-tris(triethylsilanyloxy)-tetrahydro-2H-pyran-2-carboxylic acid methyl ester 、 对乙酰氨基苯甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以81%的产率得到6-[2-(4-acetylamino-benzoylamino)-phenylcarbamoyloxy]-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