1,8-diacetoxy-10-[(4-benzyloxybenzoyloxy)-4-benzyloxyphenylmethylene]-9(10H)-anthracenone | 209347-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-diacetoxy-10-[(4-benzyloxybenzoyloxy)-4-benzyloxyphenylmethylene]-9(10H)-anthracenone
• 英文别名: [(4,5-Diacetyloxy-10-oxoanthracen-9-ylidene)-(4-phenylmethoxyphenyl)methyl] 4-phenylmethoxybenzoate
• CAS: 209347-50-2
• 化学式: C₄₆H₃₄O₉
• 分子量: 730.771
• InChiKey: YEIGXXZPYKYLGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,8-diacetoxy-10-[(4-benzyloxybenzoyloxy)-4-benzyloxyphenylmethylene]-9(10H)-anthracenone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以20%的产率得到10-(4-benzyloxybenzoyl)-1-(4-benzyloxybenzoyloxy)-8-hydroxy-9(10H)-anthracenone
  参考文献：
  名称：

  10-Benzoyl-1,8-dihydroxy-9(10H)-anthracenones: Synthesis and biological properties

  摘要：

  The synthesis and biological properties of 10-benzoyl-1,8-dihydroxy-9(10H)-anthracenones are described. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT and the 5-lipoxygenase enzyme in bovine polymorphonuclear leukocytes. In addition. generation of hydroxyl radicals was determined as measured by deoxyribose degradation. The results obtained with the new compounds show that substitution with a 4-hydroxy (4f) or a 4-benzyloxy group (4i) at the phenyl ring of the C-10 substituent resulted in potent antiproliferative agents. No correlation was found between hydroxyl-radical formation and the 5-LO inhibitory or antiproliferative action of the compounds. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80010-x
• 作为产物：
  描述：

  4-苯甲氧基苯(甲)酰氯 、 1,8-diacetyloxy-9(10H)-anthracenone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以27%的产率得到1,8-diacetoxy-10-[(4-benzyloxybenzoyloxy)-4-benzyloxyphenylmethylene]-9(10H)-anthracenone
  参考文献：
  名称：

  10-Benzoyl-1,8-dihydroxy-9(10H)-anthracenones: Synthesis and biological properties

  摘要：

  The synthesis and biological properties of 10-benzoyl-1,8-dihydroxy-9(10H)-anthracenones are described. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT and the 5-lipoxygenase enzyme in bovine polymorphonuclear leukocytes. In addition. generation of hydroxyl radicals was determined as measured by deoxyribose degradation. The results obtained with the new compounds show that substitution with a 4-hydroxy (4f) or a 4-benzyloxy group (4i) at the phenyl ring of the C-10 substituent resulted in potent antiproliferative agents. No correlation was found between hydroxyl-radical formation and the 5-LO inhibitory or antiproliferative action of the compounds. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80010-x

文献信息

• 10-Benzoyl-1,8-dihydroxy-9(10H)-anthracenones: Synthesis and biological properties
  作者：Klaus Müller、Reinhold Altmann、Helge Prinz

  DOI：10.1016/s0223-5234(98)80010-x

  日期：1998.3

  The synthesis and biological properties of 10-benzoyl-1,8-dihydroxy-9(10H)-anthracenones are described. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT and the 5-lipoxygenase enzyme in bovine polymorphonuclear leukocytes. In addition. generation of hydroxyl radicals was determined as measured by deoxyribose degradation. The results obtained with the new compounds show that substitution with a 4-hydroxy (4f) or a 4-benzyloxy group (4i) at the phenyl ring of the C-10 substituent resulted in potent antiproliferative agents. No correlation was found between hydroxyl-radical formation and the 5-LO inhibitory or antiproliferative action of the compounds. (C) Elsevier, Paris.