(S)-10-(2-benzyloxycarbonylamino-1-oxo-3-phenylpropyl)-1,8-dihydroxy-9(10H)-anthracenone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (S)-10-(2-benzyloxycarbonylamino-1-oxo-3-phenylpropyl)-1,8-dihydroxy-9(10H)-anthracenone
• 英文别名: benzyl N-[(2S)-1-(4,5-dihydroxy-10-oxo-9H-anthracen-9-yl)-1-oxo-3-phenylpropan-2-yl]carbamate
• 化学式: C₃₁H₂₅NO₆
• 分子量: 507.543
• InChiKey: AZIMDZDCLSZTAG-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  地蒽酚 、 N-benzyloxycarbonyl-L-phenylalanyl chloride 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以10%的产率得到(S)-10-(2-benzyloxycarbonylamino-1-oxo-3-phenylpropyl)-1,8-dihydroxy-9(10H)-anthracenone
  参考文献：
  名称：

  10-α-Aminoacyl-9(10H)-anthracenones: Inhibition of 12(S)-HETE Biosynthesis and HaCaT Cell Growth

  摘要：

  1,8-Dihydroxy-9(10H)-anthracenones with a 10-alpha-aminoacyl group were synthesized using either a mixed-anhydride coupling method or Boc-protected oxazolidinediones. The novel anthracenones were evaluated as inhibitors of the biosynthesis of 12(S)-hydroxyeicosatetraenoic acid (12(S)-HETE) in epidermal homogenate of mice and for inhibition of the growth of HaCaT keratinocytes. These cells were also tested for their susceptibility for the action of the most potent members of this series on plasma membrane integrity, in order to confirm that inhibition of cell growth is not a result of membrane damage induced by prooxidants released from anthracenones. Hydroxyl-radical generation as measure of the prooxidant potential of the compounds was determined by deoxyribose degradation. The most potent analogues of this series were equally potent as anthralin against 12(S)-HETE biosynthesis and keratinocyte proliferation, while oxygen-radical generation and the resulting damage to cell membrane was strongly reduced as compared to the antipsoriatic drug.

  DOI：

  10.1002/(sici)1521-4184(19991)332:1<31::aid-ardp31>3.0.co;2-t

文献信息

• 10-α-Aminoacyl-9(10H)-anthracenones: Inhibition of 12(S)-HETE Biosynthesis and HaCaT Cell Growth
  作者：Klaus Müller、Klaus Breu

  DOI：10.1002/(sici)1521-4184(19991)332:1<31::aid-ardp31>3.0.co;2-t

  日期：1999.1

  1,8-Dihydroxy-9(10H)-anthracenones with a 10-alpha-aminoacyl group were synthesized using either a mixed-anhydride coupling method or Boc-protected oxazolidinediones. The novel anthracenones were evaluated as inhibitors of the biosynthesis of 12(S)-hydroxyeicosatetraenoic acid (12(S)-HETE) in epidermal homogenate of mice and for inhibition of the growth of HaCaT keratinocytes. These cells were also tested for their susceptibility for the action of the most potent members of this series on plasma membrane integrity, in order to confirm that inhibition of cell growth is not a result of membrane damage induced by prooxidants released from anthracenones. Hydroxyl-radical generation as measure of the prooxidant potential of the compounds was determined by deoxyribose degradation. The most potent analogues of this series were equally potent as anthralin against 12(S)-HETE biosynthesis and keratinocyte proliferation, while oxygen-radical generation and the resulting damage to cell membrane was strongly reduced as compared to the antipsoriatic drug.