(3aR,4R,8R,8aR)-6-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-3a,4,5,7,8,8a-hexahydro-[1,3]dioxolo[4,5-d]azepine-4,8-diol | 404961-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,4R,8R,8aR)-6-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-3a,4,5,7,8,8a-hexahydro-[1,3]dioxolo[4,5-d]azepine-4,8-diol
• CAS: 404961-39-3
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: NXJHPFYSZRRQBU-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,8R,8aR)-6-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-3a,4,5,7,8,8a-hexahydro-[1,3]dioxolo[4,5-d]azepine-4,8-diol 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 96.0h， 生成 C₂₉H₄₂N₂O₁₀*2ClH
  参考文献：
  名称：

  Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents

  摘要：

  The synthesis of 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p- phenoxy] and 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p-benzyloxy] propanes is reported. These compounds have been prepared to investigate the potential of incorporating iminosugars as useful recognition elements in DNA minor groove binding agents. The compounds were shown to have very moderate binding affinities for DNA in thermal denaturation and ethidium bromide displacement assays when compared with propamidine. They were also found to possess some in vitro anticancer activity that did not correlate with their DNA binding affinity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00719-3
• 作为产物：
  描述：

  3,4-di-O-isopropylidene-D-mannitol 在 原乙酸三甲酯 、 potassium tert-butylate 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 100.0h， 生成 (3aR,4R,8R,8aR)-6-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-3a,4,5,7,8,8a-hexahydro-[1,3]dioxolo[4,5-d]azepine-4,8-diol
  参考文献：
  名称：

  Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents

  摘要：

  The synthesis of 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p- phenoxy] and 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p-benzyloxy] propanes is reported. These compounds have been prepared to investigate the potential of incorporating iminosugars as useful recognition elements in DNA minor groove binding agents. The compounds were shown to have very moderate binding affinities for DNA in thermal denaturation and ethidium bromide displacement assays when compared with propamidine. They were also found to possess some in vitro anticancer activity that did not correlate with their DNA binding affinity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00719-3

文献信息

• Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents
  作者：Heather A Johnson、Neil R Thomas

  DOI：10.1016/s0960-894x(01)00719-3

  日期：2002.1

  The synthesis of 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p- phenoxy] and 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p-benzyloxy] propanes is reported. These compounds have been prepared to investigate the potential of incorporating iminosugars as useful recognition elements in DNA minor groove binding agents. The compounds were shown to have very moderate binding affinities for DNA in thermal denaturation and ethidium bromide displacement assays when compared with propamidine. They were also found to possess some in vitro anticancer activity that did not correlate with their DNA binding affinity. (C) 2002 Elsevier Science Ltd. All rights reserved.