1,8-dihydroxy-10-[(4-methoxyanilino)methylidene]anthracen-9-one | 202916-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-dihydroxy-10-[(4-methoxyanilino)methylidene]anthracen-9-one
• CAS: 202916-84-5
• 化学式: C₂₂H₁₇NO₄
• 分子量: 359.381
• InChiKey: BMTLXGFSGLFQCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  78.79
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,8-dihydroxy-10-[(4-methoxyanilino)methylidene]anthracen-9-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以40%的产率得到1,8-dihydroxy-10-[(4-hydroxyanilino)methylidene]anthracen-9-one
  参考文献：
  名称：

  10-Aminomethylene-1,8-dihydroxy-9(10H)-anthracenones: Inhibitory action against 5-lipoxygenase and the growth of HaCaT cells

  摘要：

  A novel series of 10-aminomethylene substituted 1,8-dihydroxy 9(10H)-anthracenones was synthesized and evaluated both in the bovine polymorphonuclear leukocyte 5-lipoxygenase (5-LO) and in the HaCaT keratinocyte proliferation assay for their enzyme inhibitory and antiproliferative activity, respectively. The synthesis required readily available formanilides as starting materials and a modified Vilsmeier type reaction with the parent anthracenone. The most potent inhibitor of 5-LO was a 4-hydroxyphenyl analog, whereas a 4-nitrophenyl substituent was essential for potent antiproliferative activity. The results of this study indicate that an activated double bond at C-10 of phenylalkylidene-substituted anthracenones is required for potency.

  DOI：

  10.1016/s0223-5234(97)82775-4
• 作为产物：
  描述：

  地蒽酚 、 4'-甲氧基甲酰苯胺 在 吡啶 、 N,N-二甲基丙烯基脲 、 氯化亚砜 作用下， 生成 1,8-dihydroxy-10-[(4-methoxyanilino)methylidene]anthracen-9-one
  参考文献：
  名称：

  10-Aminomethylene-1,8-dihydroxy-9(10H)-anthracenones: Inhibitory action against 5-lipoxygenase and the growth of HaCaT cells

  摘要：

  A novel series of 10-aminomethylene substituted 1,8-dihydroxy 9(10H)-anthracenones was synthesized and evaluated both in the bovine polymorphonuclear leukocyte 5-lipoxygenase (5-LO) and in the HaCaT keratinocyte proliferation assay for their enzyme inhibitory and antiproliferative activity, respectively. The synthesis required readily available formanilides as starting materials and a modified Vilsmeier type reaction with the parent anthracenone. The most potent inhibitor of 5-LO was a 4-hydroxyphenyl analog, whereas a 4-nitrophenyl substituent was essential for potent antiproliferative activity. The results of this study indicate that an activated double bond at C-10 of phenylalkylidene-substituted anthracenones is required for potency.

  DOI：

  10.1016/s0223-5234(97)82775-4

文献信息

• 10-Aminomethylene-1,8-dihydroxy-9(10H)-anthracenones: Inhibitory action against 5-lipoxygenase and the growth of HaCaT cells
  作者：K Müller、A Sellmer、H Prinz

  DOI：10.1016/s0223-5234(97)82775-4

  日期：1997.11

  A novel series of 10-aminomethylene substituted 1,8-dihydroxy 9(10H)-anthracenones was synthesized and evaluated both in the bovine polymorphonuclear leukocyte 5-lipoxygenase (5-LO) and in the HaCaT keratinocyte proliferation assay for their enzyme inhibitory and antiproliferative activity, respectively. The synthesis required readily available formanilides as starting materials and a modified Vilsmeier type reaction with the parent anthracenone. The most potent inhibitor of 5-LO was a 4-hydroxyphenyl analog, whereas a 4-nitrophenyl substituent was essential for potent antiproliferative activity. The results of this study indicate that an activated double bond at C-10 of phenylalkylidene-substituted anthracenones is required for potency.