3,4,5-triacetoxy-6-{4-[(2-(4-acetylamino-benzoylamino)-phenylcarbamoyl)oxymethyl]-2-nitro-phenoxy}-tetrahydro-2H-pyran-2-carboxylic acid methyl ester | 1075719-60-6

• 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-{4-[(2-(4-acetylamino-benzoylamino)-phenylcarbamoyl)oxymethyl]-2-nitro-phenoxy}-tetrahydro-2H-pyran-2-carboxylic acid methyl ester
• CAS: 1075719-60-6
• 化学式: C₃₆H₃₆N₄O₁₆
• 分子量: 780.699
• InChiKey: UCSYVBQMLFYMOX-NRNQRDPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  263.33
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  3,4,5-triacetoxy-6-{4-[(2-(4-acetylamino-benzoylamino)-phenylcarbamoyl)oxymethyl]-2-nitro-phenoxy}-tetrahydro-2H-pyran-2-carboxylic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以40%的产率得到6-{4-[(2-(4-acetylamino-benzoylamino)-phenylcarbamoyl)oxymethyl]-2-nitro-phenoxy}-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：

  (2S,3S,5R,6S)-2-(methoxycarbonyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 、 4-乙酰氨基-N-(2'-氨基苯基)-苯甲酰胺 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以60%的产率得到3,4,5-triacetoxy-6-{4-[(2-(4-acetylamino-benzoylamino)-phenylcarbamoyl)oxymethyl]-2-nitro-phenoxy}-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